Chicago Date Night

A Virgin Experience Gifts Collection

(103 Reviews)

From: $199

Romantic Chicago Experiences for Couples

Let Them Choose Their Perfect Date!

Take the guesswork out of gift-giving and let your friend or loved one choose their perfect date with this Chicago Date Night collection!

Our handpicked selection of top-rated experiences for two allows the happy couple to select the experience of their choice and book a date convenient for them.

Whether seeking a picturesque sunset paddle or an adrenaline-filled adventure to remember - this Date Night gift has something for every type of couple!

Price: $199

Quantity:

Give.

Give the gift of romance with a handpicked selection of our favorite experiences for couples.

Book.

Your recipient selects their dream date and books a time convenient for them.

Enjoy!

Go out, have fun, and create a memory to last a lifetime!

Summary

Let Them Choose Their Perfect Date!

Take the guesswork out of gift-giving and let your friend or loved one choose their perfect date with this Chicago Date Night collection!

Our handpicked selection of top-rated experiences for two allows the happy couple to select the experience of their choice and book a date convenient for them.

Whether seeking a picturesque sunset paddle or an adrenaline-filled adventure to remember - this Date Night gift has something for every type of couple!

Do I have to choose the experience at the time of purchase?

No - This Date Night gift is different from our other experience vouchers because you are giving your recipient the gift of choice! We have handpicked a collection of our top-rated experiences for couples and your recipient can choose which experience they would like to do and when.

Of course if your recipient chooses to do an experience not included in the Date Night Collection, they are welcome to exchange this gift and apply the monetary value of the voucher toward any other experience on our site.

Is this Date Night gift exchangeable?

Absolutely! The value of this package can be applied towards any experience on the site. To exchange, click on the "My Vouchers" tab in your account.

Does this gift have any restrictions?

No, but some experiences included do have differing guidelines for things like age, weight, and height. Please be mindful of these restrictions when choosing your perfect date!

What if the experience chosen costs less than the voucher?

No problem! Your recipient will have the balance to use for future bookings toward any experience on the site.

Tour for 2

Lakefront Bike Tour

Tour for 2

(3)

Kayak Tour at Night

Tour for 2

(4)

iFly Indoor Skydiving - Lincoln Park

2 Flights for 2

iFly Indoor Skydiving - Naperville

2 Flights for 2

iFly Indoor Skydiving - Rosemont

2 Flights for 2

Walking Chicago Pizza Tour

Tour for 2

Wedding Dance Lessons

1 Hour of Dance Lessons

(1)

Self-Guided Deep Dish Pizza Tour

Tour for 2

River North Food Tour

Tour for 2

(2)

Murder Mystery Dinner Show

Dinner for 2

(8)

Chicago Walking Food Tour

Tour for 2

Chinatown Food & Culture Tour

Tour for 2

(1)

Ultimate Chicago Food & Bike Tour

Tour for 2

Below are 103 reviews from experiences included in this collection:

View More Reviews:

Chinatown Food & Culture Tour Chicago Date Night Nov 10, 2021 By: Melissa G

Nick was great. Very nice and friendly. Food was plentiful and in various parts of old and new Chinatown.

Response from Virgin Experience Gifts

Hi Melissa! I think YOU are great, for leaving such a wonderful review! It's delightful to hear how much Nick added to your overall experience, clearly you were in the best hands. I hope the food was savory and getting to immerse yourself in the culture of Chicago's Chinatown was sweet, on this unique touring experience. All my best, Courtney

Wedding Dance Lessons Chicago Date Night Sep 24, 2021 By: Jeff P

Our instructor was very nice and helpful. She made us feel comfortable and at-ease the entire time!

Response from Virgin Experience Gifts

Hi Jeff! I am so thrilled you enjoyed your Wedding Dance Lessons and that your instructor provided you with a laid back and pleasant atmosphere. I sincerely hope your choreographed twirls, dips, and spins impress your wedding guests and that you can cherish these magical moments for years to come! All my best, Elizabeth

Architectural Kayak Tour Chicago Date Night Sep 23, 2021 By: Jon K

Our guides were great!

Response from Virgin Experience Gifts

Hello Jon! I think you’re great for embarking on this unique adventure! Ecstatic to hear you enjoyed your guides, I hope they provided you with a fascinating look into Chicago’s architectural history from the perspective of your kayak. Cheers! Courtney

Architectural Kayak Tour Chicago Date Night Sep 10, 2021 By: Lisa P

The guide and other staff were great. Lots of positive energy all around. Highly recommend knowing your fitness level before going on one of these. Three hours is a lot of paddling!

Response from Virgin Experience Gifts

Hi Lisa! Great staff and positive energy sound like an excellent combo for your paddle on the Chicago River! Three hours does sound like a lot of paddling, but I hope the sight seeing of Chicago’s Historic Buildings was everything you imagined it’d be. I appreciate your feedback on knowing your fitness level and will be sure to pass that along to future paddlers! Cheers! Courtney

Architectural Kayak Tour Chicago Date Night Sep 10, 2021 By: Frank R

It is safe. I went with my two kids and wife. The instructor was near who need him. And all over it was great!

Response from Virgin Experience Gifts

Hello Frank! What an incredible review for a wonderful adventure! It is so great to hear that you had such a 5-star experience with your guide and your family. Being safe is an absolute must so we are thrilled that you could experience this together! Best, Brianna

Pizza Tour Chicago Date Night Aug 17, 2021 By: Melissa G

Jonathan is a true gem! He is very animated and engaging the whole time. Thank you for making our tour so enjoyable.

Response from Virgin Experience Gifts

Hi there, Melissa! Thanks so much for leaving such a great review! I was actually just on the phone with Jon and was able to share your glowing review with him. He was so happy! I know they've been rearing up to begin offering tours again and made sure to make things even better than before! I'm so happy you were able to have a great time with some great people and pizza! Cheers, Jake.

River North Food Tour Chicago Date Night Aug 02, 2021 By: Eric V

Very good, and informative. One suggestion, we found out the the company doing the tours had additional restaurant -dining options that we would have preferred over this one. While we greatly enjoyed it, as residents of greater Chicagoland we would have picked one with all hidden gems over this one , which has some but also had Portillos and Lou Malnatis , great for out of towners but we go to both regularly. We did not see those options on the website

Response from Virgin Experience Gifts

Hello Eric! Thank you kindly for sharing your experience! We greatly appreciate your feedback regarding the hidden gems of Chicago and we will work with our experience providers to ensure we provide all of the experiences. However, despite revisiting some restaurants, we are thrilled to hear that you greatly enjoyed your time being a tourist in your own backyard! Kind Regards, Brianna

River North Food Tour Chicago Date Night Jul 27, 2021 By: Joyce H

The River North Food Tour was excellent in many ways! There was a good variety of restaurants on the tour, and the food was great! We walked from restaurant to restaurant, and along the way, our tour guide talked about the buildings we passed by, Chicago sports figures, and some history about the city.

Response from Virgin Experience Gifts

Hi Joyce, Thank you for taking the time to write this beautiful review! It so delightful to hear that you had such an amazing experience and learned so much during your tour. Our experience providers work so hard to provide a fulfilling and exciting tour and it sounds like you were able to witness it first hand. Cheers to amazing food and the history of Chicago! Kind Regards, Brianna

Sunset Kayak Tour Chicago Date Night Jun 25, 2021 By: Allyson D

Excellent guides Always aware of weather situation

Response from Virgin Experience Gifts

Hi Allyson, We're so glad you had a great time out on our Sunset Kayak Tour! The safety of our customers is always our number one priority and we're very pleased that your guides took such great care of you while out on the water! Cheers to more fun adventures in the future! With our best, Garrett

Architectural Kayak Tour Chicago Date Night Oct 01, 2020 By: Valerie K

It was great. I enjoyed the trip and David our tour guide was amazing. He was very knowledgeable of the history and kayak skills.

Response from Virgin Experience Gifts

Hello Valerie, Fantastic! I am overjoyed to hear you enjoyed your time on the water for this wonderful kayak adventure. We are so happy that David could provide you with some great information on your tour. We will be sure to pass along your kind words to him! Thank you so much for sharing your experience with us. Cheers, Chandi

Fireworks Kayak Tour Chicago Date Night Jul 21, 2020 By: Grant S

It was a lot of fun and encouraged us to potentially go again!

Response from Virgin Experience Gifts

Hi there Grant! So happy to hear you had such a great time. We would love to get you out for round 2 whenever you are ready! Cheers, Chandi

Murder Mystery Dinner Show Chicago Date Night Feb 21, 2020 By: Ashley K

The murder mystery was fun! The food options were good and the acting was amusing. There was a bit of time to socialize but not really enough to investigate more than 2 people. The documentation said iced tea and coffee included, but it was not offered to our table at all. The servers dropped off the food and did not come back, so if something was wrong or missing, there was no opportunity to have it fixed.

Response from Virgin Experience Gifts

Hi there, Ashley. I am so glad to hear that despite the non-ideal beverage situation, you were able to have a blast! Our partners certainly strive to provide ample time for socializing, service, and the show - thought it is certainly a lot to orchestrate! Please do let me know next time you're looking to get out on an awesome experience! Best, Jake.

Pizza Tour Chicago Date Night Feb 07, 2020 By: Karen H

We did this as a family activity with our adult children. The whole group enjoyed the pizza and seeing the city on the clean and comfortable bus. The tour guide was great, trying to make everyone feel comfortable and ensuring people had what they needed.

Response from Virgin Experience Gifts

What a great review! Our experience providers are the best - they'll always ensure everyone is having an amazing time. I'm so glad we were able to bring you and your family together over the best pizza Chicago has to offer! Cheers, Jake.

Pizza Tour Chicago Date Night Jan 28, 2020 By: Alejandro S

The pizza was amazing and our tour guide made it even better. He was extremely knowledgeable and made the tour completely worth it. Would highly recommend.

Response from Virgin Experience Gifts

What a wonderful review, thanks so much for writing in! I'm so glad to share this with our amazing experience provider, as I know they are always striving to be the best in the biz!

Murder Mystery Dinner Show Chicago Date Night Nov 04, 2019 By: Kevin D

The experience overall was good. The show and actors were great. Dinner was good.

Response from Virgin Experience Gifts

Hi Thuy, Glad to hear you had a fun time! I hope you keep us in mind next time you want to get out on another unique adventure! Cheers, Inah

Pizza Tour Chicago Date Night Oct 15, 2019 By: Molly M

Danny was great! You not only got to try great pizza but he also gave you a tour of Chicago on the ride to the different pizzerias. Totally recommend!

Response from Virgin Experience Gifts

Hi Molly, A little history, great pizza, and a fun guide - what more can you ask for? Cheers to fun new memories in the Windy City! Warm regards, Inah

Treetop Adventure with Go Ape Chicago Date Night Oct 11, 2019 By: Maria W

Exceeded expectations! 2.5 hour obstacle course! Great time. Will be back very soon with the whole family!

Response from Virgin Experience Gifts

Hi Maria, That's what we love to hear! We looking forward to hosting you again, along with your family! Cheers, Inah

Murder Mystery Dinner Show Chicago Date Night Oct 03, 2019 By: Michael B

We had a great time, very interactive. Would definitely recommend it.

Response from Virgin Experience Gifts

Wonderful, that's what we love to hear! The interaction between the actors and the guests is so integral to the show and I'm glad you enjoyed it! Did you figure out the murderer? Cheers, Inah

Architectural Kayak Tour Chicago Date Night Sep 12, 2019 By: Richard S

Excellent trip with experienced guides

Architectural Kayak Tour Chicago Date Night Sep 12, 2019 By: Bethany L

Our architectural kayak tour with Kayak Chicago was our highlight of our weekend trip to Chicago over Labor Day. The equipment is top of the line and in great shape. We received adequate paddling instruction before getting on the water. The only thing we wanted was more architectural interpretation & details, but overall it was great and definitely worth the money.

Sunset Kayak Tour Chicago Date Night Sep 03, 2019 By: Tammi O

Awesome kayaking experience. Bubba our guide was very knowledgeable and friendly. Great views of the city. We would definitely do it again. Thanks Kayak Chicago!

Architectural Kayak Tour Chicago Date Night Sep 03, 2019 By: Maggie O

Great tour! The guides were super knowledgeable about the history & architecture, were very attentive to the whole group, and were hilarious! Also they gave lots of great tips prior to getting in the water for how to navigate of it was your first time kayaking. 10/10 would recommend this excursion!

Response from Virgin Experience Gifts

Hi there Maggie! WOW! What an awesome review! We will be sure to pass the kind words on to our partners. We are overjoyed to hear that not only was a very informative and educational experience, it was exciting, funny, and beginner friendly! Looking forward to getting out on the water again soon. Best, Sophia

Treetop Adventure with Go Ape Chicago Date Night Aug 05, 2019 By: Victoria D

The zip lining adventure was amazing and a lot of fun. The booking through cloud 9 was confusing and took a while for the codes to be activated. The coure was about 2 to 3 hours long and used a lot of upper body strength to climb the different courses to get to each zip lining.

River & Lake Architectural Cruise Chicago Date Night Aug 05, 2019 By: Sandra H

Tour guide Griffin was great!

River & Lake Architectural Cruise Chicago Date Night Jul 22, 2019 By: Robert K

We enjoyed the cruise very much. The crew was great especially the guide, her name was like Tequila, very informative and entertaining, BUT the trip ended abruptly because of a down pour while in the locks on the way back. She kept order and safety. But we were not able to thank her or tip her for that matter. I would of liked to talk to her at the end.

Sunset Kayak Tour Chicago Date Night Jul 17, 2019 By: Serica R

This was a great night! The tour was the perfect length and the guide was fantastic.

Kayak Tour at Night Chicago Date Night Jul 16, 2019 By: Paula K

So much fun! This is a well-organized event with plenty of instruction prior to hitting the river. It was a beautiful night, full of gorgeous sights along the Chicago River, and a good workout, too! Highly recommended!

Murder Mystery Dinner Show Chicago Date Night Apr 29, 2019 By: Angela V

This was different than what I expected. The audience is part of the show. The experience is not like other events I have attended where there is a stage this is set in a banquet hall and is interactive. I enjoy watching more than participating. The food was great.

Response from Virgin Experience Gifts

Hi Angela, Thank you for taking the time to write in about your experience. The Murder Mystery Dinner Show is certainly a unique experience, and a big aspect of what sets it apart from other such shows is the interactivity. The actors even sit among the audience to further enhance the feeling of being part of the show! I understand how that can be overlooked in reading the description, and I'm sorry that the evening wasn't what you expected. I am glad to hear that the food was a shining moment though! If you ever feel like exploring another adventure that may be more to your liking, I've placed a $25 voucher into your account for use towards booking a different experience! Warm Regards, Inah

Murder Mystery Dinner Show Chicago Date Night Mar 01, 2019 By: Rick B

Great time

Response from Virgin Experience Gifts

Hi Rick, A great time for a great customer, thanks for sharing! Cheers, Inah

Murder Mystery Dinner Show Chicago Date Night Mar 01, 2019 By: Mike &

The dinner theater was so much fun. Food was excellent. Service was awesome, and the show was a lot of fun. Definitely recommend!

Response from Virgin Experience Gifts

Hi Heather, Thank you for taking the time to write a review. I'm so happy to hear you had a great experience. Let us know when you feel like getting out on another adventure! Warm Regards, Inah

Murder Mystery Dinner Show Chicago Date Night Feb 22, 2019 By: Nicole K

Murder Mystery Dinner Show was a blast! I can’t wait to do it again!

Response from Virgin Experience Gifts

Hi Nicole, That's wonderful! Let us know when you feel like honing your detective skills even more! Cheers, Inah

Pizza Tour Chicago Date Night Jan 22, 2019 By: Mary H

We had so much fun on this tour! Danny, our tour guide, was very knowledgable and personable. There was a great choice of pizza places...not your big name chains. The pizza was amazing...some of the best pizza we've had! The ride to each place provided a view of the city along with some history and information about each neighborhood. This tour is a must do!

Response from Virgin Experience Gifts

Hi Lisa, Thank you so very much for your kind words! I'll be sure to pass your compliments on to Danny. I know our tour guides take a lot of pride in showing their guests off-the-beaten-path spots and imparting their knowledge about the city. Cheers to great pizza and new Chicago memories! Warm Regards, Inah

Pizza Tour Chicago Date Night Jan 22, 2019 By: Hope S

It was incredible! I felt like I was on a fun field trip. I learned so much about Chicago pizza along with some general history of Chicago. Our tour guide, Danny, was also fabulous and I loved his enthusiasm!

Response from Virgin Experience Gifts

Hi Hope, We happen to think you're incredible! Great pizza, a little history, and a fun guide - what more can you ask for? Cheers, Inah

Bikes, Bites, and Brews Tour - West Side Route Chicago Date Night Oct 12, 2018 By: Amanda W

Our tour with Bobby's Bike Hike was amazing! It wasn't the most optimal weather, but still a great time -- Courtney was enthusiastic, informative, & fun. When booking another tour, I will try to do ones that she leads. The places we stopped were great as well -- my favorite being the chocolate shop at the end! I bought a scotcharoo that was TO DIE FOR. SO GOOD.

Response from Virgin Experience Gifts

Hi Amanda, I know you were originally looking to take another tour and I'm happy to hear that we were able to send you out on an experience just as great, even though Mother Nature wasn't being cooperative. I'll be sure to pass your kind words along to Courtney! Nothing like a nice chocolate treat at the end of a bike ride right? Cheers, Inah

Architectural Kayak Tour Chicago Date Night Oct 08, 2018 By: Candice Y

We had an incredible time on the Architecture Kayak Tour with our host Bubba. We spent a gorgeous afternoon getting to know the city close-up during our 5-mile kayak. The tour was the highlight of our first trip to Chicago. We highly recommend Kayak Chicago!

Response from Virgin Experience Gifts

What a neat way to experience Chicago for the first time. I'm so glad to hear you had a wonderful tour with Bubba. We love working with them also! Thanks for sharing! Best, Brooke

Sunset Kayak Tour Chicago Date Night Oct 01, 2018 By: Noémie M

It was a nice tour on kayak ! Nice view of Chicago , the night , and the buildings ! Great stories !

Response from Virgin Experience Gifts

Great to hear you had kayaking. Thanks for your review! Best, Brooke

Treetop Adventure with Go Ape Chicago Date Night Sep 04, 2018 By: Ryan H

An absolute blast!! Bought this for my husband for his birthday and we had so much fun. Paired with brunch at Solstice, it was the perfect day spent together! The forest preserve is gorgeous.

Response from Virgin Experience Gifts

What a fun way to celebrate a birthday! I'm glad to hear it turned out so perfect for both of you. Thanks for writing in. Best, Brooke

Treetop Adventure with Go Ape Chicago Date Night Sep 04, 2018 By: Melody G

We registered for this zip line experience as a wedding gift and redeemed it the following summer. I loved that the timing was super flexible in terms of when we redeemed it, and we had the option to exchange it for a different experience or even add people to our reservation. We kept it as just my husband and I, and we both had a blast. The organization was very courteous and professional, responding quickly to emailed questions and giving a good training experience when we arrived at the course. The course had a great mix of daring challenges in the treetops and ziplines and was the perfect length, about 2.5 hours. Because of the way the course is spread out, it felt for a while like we were the only ones on the course and was really nice to have that privacy to enjoy the adventure as newlyweds. And it was so neat to be above the treeline at the last stop on the course! I'd highly recommend this experience to anyone who likes a little outdoor adventure and isn't too afraid of heights.

Treetop Adventure with Go Ape Chicago Date Night Sep 04, 2018 By: JULIE S

While the ropes course was acceptable - the Tarzan jump was the best part! The zip lining portion of the course was EXTREMELY disappointing! Short lines that sent you into a runway of mulch - not what I would expect from an activity labeled "Ultimate Zip Line Adventure Course". Very short slow zip lines that land your but in the dirt.

Sunset Kayak Tour Chicago Date Night Aug 28, 2018 By: Fred D

We had a great time on the sunset paddle. The staff was happy and fun. Istruction was clear and easy to understand. Great way to see the city. The river was busy with some boat traffic but I always felt safe on the "Mighty Chicago River" because the guides communicated well and at times took charge of the boat traffic.

Kayak Tour at Night Chicago Date Night Aug 28, 2018 By: Monica D

We had a great time on the night kayak tour! I purchased it for my boyfriend’s birthday and he had a great time! We were on the water for about 2 hours and it was the perfect amount of time.

Murder Mystery Dinner Show Chicago Date Night Aug 28, 2018 By: Renee W

The show was entertaining, the food was great, and we had a lot of fun!

Bikes, Bites, and Brews Tour - North Side Route Chicago Date Night Aug 28, 2018 By: Shaz &

We had a great tour guide. The choices of places to eat was great. We covered good amount of Chicago neighborhoods. I highly recommend this tour to anyone who loves biking and eating.

Treetop Adventure with Go Ape Chicago Date Night Aug 28, 2018 By: Danielle C

Very fun! Great experience!

Treetop Adventure with Go Ape Chicago Date Night Aug 28, 2018 By: Kaitlan C

Great views and challenging course - we had a great time.

Pizza Tour Chicago Date Night Jun 04, 2018 By: Wendy &

A delightful interesting tour!!! We learned many facts about Chicago and pizza!!! Everyone in our group was very friendly, easy to talk to and fun!!!

Bikes, Bites, and Brews Tour - North Side Route Chicago Date Night Jun 04, 2018 By: Jane S

Amazing , fun & worthwhile Courtney was a great guide

Pizza Tour Chicago Date Night Jul 25, 2017 By: Bob F

Received our pizza tour experience as a Christmas gift. My wife and I had a great time. Danny, our tour guide, was great. If you love pizza, this is the tour for you. We thought that we would be going to some of the "famous named" pizza places. This tour takes you to the lesser known neighborhood spots. We went to 4 different places, and had 4 different styles of pizza. An added bonus is that the tour also gives you great views of Chicago and the different neighborhoods. This tour is a must see and do!!

Treetop Adventure with Go Ape Chicago Date Night Jul 10, 2017 By: Jessica B

I had a blast at ziplining. Instructions was great. I felt like there was enough staff around to help if needed, but there was no hand-holding.They really let you experience it for yourself your way. I'd definitely go back.

Architectural Kayak Tour Chicago Date Night Sep 22, 2016 By: Cassie P

It was a beautiful day on the Chicago River, had a blast!

Pizza Tour Chicago Date Night Sep 02, 2016 By: Molly W

We loved our tour and our guide. He was very knowledgeable, funny, easy-going, and a lot of fun to hang out with for the afternoon. We loved that we not only learned about pizza but also about Chicago. I lived in Chicago for 5 years and loved actually learning about the pizza I so often enjoyed. Great tour - 5 star all the way! Thanks for the great experience!

Pizza Tour Chicago Date Night Aug 17, 2016 By: Jessica W

Pizza was great and our tour guide was awesome! I really enjoyed him. He was so funny and knowledgeable about our city. My only complaint is the amount of profanity he used, that was a little bummer, but other than that I enjoyed my experience.

Architectural Kayak Tour Chicago Date Night Aug 16, 2016 By: DarylAnn W

The kayak tour was awesome! It got tiring towards the end, but our tour guide pulled us the whole way back to the beginning! He was very funny and informative!

Bikes, Bites, and Brews Tour - North Side Route Chicago Date Night Aug 10, 2016 By: Karen L

It was good, although 13 miles might be a bit much for two hours. Could use a little more food provided given that it was over the lunch hour. And perhaps a more leisurely pace.

Fireworks Kayak Tour Chicago Date Night Aug 09, 2016 By: Stephanie P

The guides were fantastic, however way too many people were booked for the trip. It was a nightmare of people crashing into each other. Hurry up then wait. It was not a relaxing evening at all. We went as a family yet none of us were able to stay together with 20 other kayaks, all with zero experience in trying to navigate. If the group was smaller it would have been much more enjoyable. The smell was awful as well. The downtown Chicago views were fabulous, just way too many people.

River & Lake Architectural Cruise Chicago Date Night Jul 18, 2016 By: Linda A

On Navy Pier, there needs to be better signage directing patrons to the kiosk. There needs to be a better way to direct people to which line they should be in to board the boat. The tour guide on the boat is extremely negative in his comments about the city of Chicago. We also noted that the guide spent more time talking about how disgusting and dirty the river is, than he did about the architecture of the city. It was also very difficult to hear him from where we were sitting (toward the stern of the boat). Sitting at the back of the boat was a definite mistake as we were sucking in diesel fumes the entire trip. All in all, I'd not recommend this excursion to anyone and am very disappointed.

Treetop Adventure with Go Ape Chicago Date Night Jul 12, 2016 By: Bruce L

Outstanding experience. Outstanding service.

Lakefront Bike Tour Chicago Date Night Jun 28, 2016 By: Marti B

We loved our Father's Day neighborhood bike ride. Our guide was fun and very knowledgeable about Chicago. She instructed us on how to navigate the streets and sidewalks in a safe way. It was just challenging enough to be exciting, but not scary. Our weather was perfect and the ride was very enjoyable. I would recommend this bike tour to anyone who feels comfortable on a bike. It was an easy ride and the scenery was magnificent.

Pizza Tour Chicago Date Night May 31, 2016 By: Gregory L

This was a great experience. The 4 pizza places we visited were all awesome. We learned a lot about the history of pizza, and Joe (our tour guide) was great.

Sunset Kayak Tour Chicago Date Night Sep 18, 2015 By: Catriona S

Fantastic experience kayaking down the Chicago River -- what a great way to see the city. Guides were extremely friendly and knowledgeable. Three hours on the water is a long time paddling if you're not used to it, so be prepared for tired arms!

Architectural Kayak Tour Chicago Date Night Sep 08, 2015 By: Debra C

We had a lot of fun. It was a great experience. Very easy and fast booking experience.

Fireworks Kayak Tour Chicago Date Night Sep 02, 2015 By: Chad E

While I am not a water-lover, and have NO experience in kayaking, I absolutely LOVED the trip. It was very easy to do, and the guides were over-the-top friendly and amazingly helpful to a novice. This was a gift to my husband and myself, and we went with the kids on the trip -- had a blast! We would do it again!! All the staff was amazing!!!!

River & Lake Architectural Cruise Chicago Date Night Aug 27, 2015 By: Carla P

Great!

Architectural Kayak Tour Chicago Date Night Aug 14, 2015 By: Bob P

The staff didn't have our reservations and we had to show her our confirmation email. The trip was great though. I recommended this tour to my boss, & he is booking his family's adventure shortly.

Architectural Kayak Tour Chicago Date Night Jul 31, 2015 By: Lori K

Enjoyed the kayaking. Wished that the group was smaller. 27 was too large to hear what the guide was saying. It also made it difficult to kayak -- bumping and crashing. Wish the tour covered more architectural information. I thought that we would hear more about the buildings. Seems to be more a short history lesson. Still was fun, but not what was expected.

Architectural Kayak Tour Chicago Date Night Jul 17, 2015 By: Thomas M

We love our guide and the overall experience. The only issue was that the location is a bit removed from downtown, so it does mean a fairly long paddle to get downtown and to return to the starting point. But the guide made it enjoyable with stops along the way.

Kayak Tour at Night Chicago Date Night Jul 15, 2015 By: Martin H

The instructors were helpful. They clearly knew lots about the city, but only shared a little. One story of the loss of the SS Eastland ship was fascinating and well told. More of this would have been great.

Sunset Kayak Tour Chicago Date Night Jul 01, 2015 By: Nicole R

It was a getaway I had surprised my husband with and am so glad I did! It was a blast and I would go again.

Bikes, Bites, and Brews Tour - North Side Route Chicago Date Night Jun 25, 2015 By: Amanda K

Hands down BEST tour I've ever been on. Gabe was an incredible tour guide. He was knowledgeable, friendly and definitely went the extra mile to make sure everyone was informed, entertained, & enjoying their time on the tour. The equipment provided was in excellent condition. Already planning a subsequent trip with more friends for this fall!

Pizza Tour Chicago Date Night Feb 17, 2015 By: Carol B

The pizzas were varied and wonderful. Jonathan was a fabulous guide, who shared lots of interesting history about pizza and Chicago along the way. We look forward to doing this tour again with out-of-town visitors.

Bikes, Bites, and Brews Tour - North Side Route Chicago Date Night Nov 06, 2014 By: Jill K

Spent our 15th anniversary celebration with Gabe. He did a fabulous job with Bikes, Bites and Brew tour despite the November wind and chill. Cloud 9 Living went above and beyond notifying the bakery of our anniversary. Swirlz made us special cupcakes for the occasion! Great tour, great guide, great fun!

Lakefront Bike Tour Chicago Date Night Oct 28, 2014 By: Michael P

It was a great time. Everything was speedy and efficient.

Architectural Kayak Tour Chicago Date Night Sep 10, 2014 By: John S

I had an awesome time! The guides were great! Dave truly knows his Chicago history, architecture, and is guaranteed to make you smile and laugh, even if you become exhausted. The whole staff was fantastic. Truly professional and a fun sense of humor. I HIGHLY RECOMMEND THIS EXPERIENCE!

Pizza Tour Chicago Date Night Jun 17, 2014 By: Anna K

I enjoyed the Chicago Pizza Tour. Something to consider going forward, Some guests may only eat cheese pizza. The current structure of the tour does not allow them to ask for cheese as an alternative to what has been ordered. Maybe make an announcement at the beginning of the tour thta should you prefer cheese only it is available.

Bikes, Bites, and Brews Tour - North Side Route Chicago Date Night Jun 16, 2014 By: Monique M

Awesome trip!

Lakefront Bike Tour Chicago Date Night May 21, 2014 By: Michelle G

Gabe was a very knowledgable guide. We learned a lot about Chicago. We were able to look at the city the next few days and appreciate what we were seeing. It was a great ride, very easy and flat. The bikes were in great condition. The staff and Bobby's Bike owner also chatted with us. Very friendly staff - great tour.

Pizza Tour Chicago Date Night Sep 19, 2013 By: Leslie K

Excellent way to learn about Chicago history along with the background on pizza families and the art of this dining phenomenon. Jonathan was an excellent tour guide!

Architectural Kayak Tour Chicago Date Night Sep 06, 2013 By: Sylvie L

My only criticism is that the first part (and last, since we come back that way) of the canal stinks. The tour itself was really interesting. Full of information.

Sunset Kayak Tour Chicago Date Night Aug 19, 2013 By: Kirsten K

We had a wonderful time paddling around the city and we can't wait to try it again!

Bikes, Bites, and Brews Tour - North Side Route Chicago Date Night Aug 19, 2013 By: Shannon K

It was so refreshing to take part in something that allowed us to be tourists for the day and to learn about some hidden gems in Chicago! We did it as an anniversary celebration and it was awesome to try something new. I wouldn't be surprised if we do our own "Bikes, Bites and Brews tours" sampling new foods and drinks around this great city, feeling inspired!

Pizza Tour Chicago Date Night Jan 22, 2013 By: Alison S

Awesome tour! Absolutely loved each pizza place we went to and the history behind the pizzerias was fascinating. HIGHLY RECOMMEND!

Pizza Tour Chicago Date Night Jan 22, 2013 By: Timothea M

Guide was very knowledgeable about the history and the city. He was enthusiastic. Booking process was simple.

Sunset Kayak Tour Chicago Date Night Nov 28, 2012 By: Christa H

Todd, our guide, did a fantastic job of preparing us for our kayaking adventure. Even though we had kayaked before, his training session taught us a great deal and made our experience even better! We had a beautiful evening, great company, and a helpful and patient guide. Thank you so very much!

Architectural Kayak Tour Chicago Date Night Oct 08, 2012 By: Diane S

Very nice trip, it was nice to be able to switch from the evening paddle to a day time trip since we booked so late in the season. Great way to see the city. Was a little rough where the bigger boats were traveling, but overall a very enjoyable paddle.

Architectural Kayak Tour Chicago Date Night Oct 08, 2012 By: Joanne M

Wow! Such a great and well planned kayaking trip. The staff were friendly and nothing was a bother. They were open to questions & feedback and keeping us all safe on the water. The knowledge was well delivered. I will be looking to purchase this experience for friends coming over to visit Chicago for the first time.

Bikes, Bites, and Brews Tour - North Side Route Chicago Date Night Aug 23, 2012 By: Kathia G

Refreshing look at the city not just for tourists. I booked this tour as an anniversary present for myself and boyfriend (he is from Chicago) and he couldn't stop saying how cool it was and didn't know half of the things the tour guide was telling us about along the way.

Bikes, Bites, and Brews Tour - North Side Route Chicago Date Night Jul 18, 2012 By: Kris K

My wife and I had a great time. Weather was perfect. Great pace. We would definitely do it again.

Fireworks Kayak Tour Chicago Date Night Jul 14, 2012 By: Tracy R

We had a good experience with Cloud 9. We went with Kayaking Chicago on the fireworks tour. We received good enough instructions regarding how to kayak prior to our excursion. However, our only feedback is for Kayaking Chicago and that is to give more of an orientation prior to the excursion regarding conditions, timing, program, etc.

Fireworks Kayak Tour Chicago Date Night Jul 13, 2012 By: Lynne T

The group was extremely large especially for an evening event. There was so much attention being paid to safety and managing a large group that it really lost the recreational aura and was more of an exercise. The paddling was cumbersome because we had to stay so close together and we had to stop quite often to wait for others or stay out of the way. I think smaller groups (10 max.)with friendlier guides would have completely changed the experience. I completely understand the goal of safety, but if you are agreeing to take 50+ people out on the chicago river all at one time, in the dark, on a very busy night; it changes the whole experience. I have kayaked a lot in the wilderness and I would not recommend this event at all. I am glad I did it because I have always wanted to, but I would never do it again. I think Kayak Chicago just loaded up their list for profit and it spoiled it for me. I was told that this size group is typical for a booking and that is the reason I would never recommend this trip. Thanks Cloud 9. I appreciate your help.

Fireworks Kayak Tour Chicago Date Night Jul 09, 2012 By: DAVID C

The times listed on the booking (8-10pm) were not accurate. The experience lasted until 11:30pm. This would have been fine if we had known this ahead of time. Instead we were scrambling to return to our hotel, change, and find dinner after midnight.

Pizza Tour Chicago Date Night Jun 29, 2012 By: Kristen C

John, our tour guide, was absolutely wonderful. Even though we love pizza, we literally tried four different types of pizza that we had never had. We would go on this tour again.

Pizza Tour Chicago Date Night Jun 26, 2012 By: Lisa G

My only complaint was that nowhere (on the Cloud 9 experience description or on the confirmation from Chicago Pizza Tours) did it say anything about parking at the restaurant where we met. Therefore, I made the mistake of assuming -- since my husband and I are local to Chicago and are familiar with going downtown -- that Pizano's would have valet parking, which is normally reasonably priced at even the most high-end Chicago restaurants. We arrived within the appointed meeting time, only to find there was no valet parking. So we went to the nearest self-park garage and were disappointed at having to choose this option as, in our experience, self-park garages can be as much as $23 for 3+ hours. However, we figured it might be less because it was Sunday afternoon. Following the experience, we were stuffed and on a bit of a high from the good time we'd had and the new people we'd met. When we paid for our parking we were shocked to see that we were charged $32 for a little over four hours. It literally almost ruined the day and left a terrible taste in our mouth as our final impression of the experience. We had splurged on this experience and would NOT have purchased it knowing that we'd shell out another $32 (almost half the cost of the experience itself) for parking. But my biggest issue with it is that I wasn't EXPECTING it and I feel that either Cloud 9 or Chicago Pizza Tours should have given us some idea about the parking and we could have planned accordingly. Again, I go downtown frequently and when I know to plan ahead, I use ParkWhiz and can get very inexpensive parking near any location. I feel very upset that I didn't do so, but again, I feel like parking instructions should have been made clear to the purchaser of the experience. In closing, I would ONLY recommend Cloud 9/Chicago Pizza Tours with the huge caveat of "buyer beware" as it relates to parking!

Pizza Tour Chicago Date Night Jun 20, 2012 By: Denise J

The experience turned out to be beyond our prior anticipations! Being natives of the area we learned so much more and enjoyed the tasty selections. Loved the guide and pilot! Very knowledgeable and friendly, lots of fun!!!-Tom Janusz

Fireworks Kayak Tour Chicago Date Night Jun 11, 2012 By: Jay R

It was a good work out experience without any prep and training as a first timer. I wish the kayaks were ready and moved to the water or if there were dollies or carages available for them. I was not very happy waiting in line, carrying my own kayak while I have paid to have a good experience.

Kayak Tour at Night Chicago Date Night May 22, 2012 By: Lada R

It was beautiful! Thank You!

Pizza Tour Chicago Date Night Apr 04, 2012 By: Linda H

It is not often that you see a tour guide who is so passionate about what he does. Chicago Pizza Tour was as inspiring as it was fun...all due to the passion of Joe, the owner and guide. Four thumbs up from my group!!!

Private Art Lessons Chicago Date Night Oct 31, 2011 By: Mark S

It was a great session. I was early and they were accommodating. They were friendly, knowledgeable, and provided a positive experience. They spent the time to answer all my questions thoroughly and were encouraging.

Architectural Kayak Tour Chicago Date Night Sep 19, 2011 By: Dennis K

Had an absolutely wonderful time. As a long time Chicago area resident I thought I knew the river....I was given a very different and unique view of it. My guide Brad was exceptional.

Fireworks Kayak Tour Chicago Date Night Sep 12, 2011 By: Paul S

Fantastic experience! My wife and I had fun starting with the instruction through the end. The guides were very knowledgeable and dedicated to kayaking. We had a great time and will probably go again.

Pizza Tour Chicago Date Night Aug 23, 2011 By: Lawrence P

Well run. Guide-well informed/knowledge re: pizza. Great fellow tourists. Good overall experience.

Architectural Kayak Tour Chicago Date Night Aug 08, 2011 By: Lisa T

Our experience was awesome! Our guide was fun and informative and made the experience great! Having never been in a kayak before our guide made me feel relaxed and taught me enough about the in's and out's of paddling a kayak to make me feel comfortable. Thanks for a great adventure!

Pizza Tour Chicago Date Night Aug 06, 2011 By: Christopher O

It's too expensive.

Fireworks Kayak Tour Chicago Date Night Jun 27, 2011 By: Cynthia Z

What a great experience and what a workout! The tour guides helped us feel comfortable and safe on our trip. We loved watching the fireworks from a different point of view. Great time! We'd definitely recommend it to our friends!

$199 Chicago Date Night

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Experiences Included

Escape Room

Treetop Adventure with Go Ape

Pizza Tour

Architectural Kayak Tour

Bikes, Bites, and Brews Tour - North Side Route

Fireworks Kayak Tour

Bikes, Bites, and Brews Tour - West Side Route

Private Art Lessons

Sunset Kayak Tour

River & Lake Architectural Cruise

Ultimate City Bike Tour

Lakefront Bike Tour

Kayak Tour at Night

iFly Indoor Skydiving - Lincoln Park

iFly Indoor Skydiving - Naperville

iFly Indoor Skydiving - Rosemont

Walking Chicago Pizza Tour

Wedding Dance Lessons

Self-Guided Deep Dish Pizza Tour

River North Food Tour

Murder Mystery Dinner Show

Chicago Walking Food Tour

Chinatown Food & Culture Tour

Ultimate Chicago Food & Bike Tour

Customer Reviews

Not Sure? Let them choose.

Chicago Date Night

A Virgin Experience Gifts Collection

Let Them Choose Their Perfect Date!

How It Works

Give.

Book.

Enjoy!

Summary

Let Them Choose Their Perfect Date!

Frequently Asked Questions

Experiences Included

Escape Room

Treetop Adventure with Go Ape

Pizza Tour

Architectural Kayak Tour

Bikes, Bites, and Brews Tour - North Side Route

Fireworks Kayak Tour

Bikes, Bites, and Brews Tour - West Side Route

Private Art Lessons

Sunset Kayak Tour

River & Lake Architectural Cruise

Ultimate City Bike Tour

Lakefront Bike Tour

Kayak Tour at Night

iFly Indoor Skydiving - Lincoln Park

iFly Indoor Skydiving - Naperville

iFly Indoor Skydiving - Rosemont

Walking Chicago Pizza Tour

Wedding Dance Lessons

Self-Guided Deep Dish Pizza Tour

River North Food Tour

Murder Mystery Dinner Show

Chicago Walking Food Tour

Chinatown Food & Culture Tour

Ultimate Chicago Food & Bike Tour

Customer Reviews

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