A diverse cultural scene unlike any other in the US, the third largest city in the country with more things to do than you could ever think possible: there’s a reason Chicago is one of America’s most visited cities. From its impressive architecture to delicious food trends like deep dish pizza, there’s quite literally something for everyone to enjoy here.
Whether it’s exploring the area by foot, taking to the water with a cruise or uncovering its Irish heritage, Chicago is home to it all. Here, we’ve put together some of our favorite things to do in Chicago including can't-miss landmarks and plenty of unforgettable experiences.
Dining Cruises
This outing is without doubt one of the best things to do in Chicago. A dining cruise is the perfect way to enjoy a few hours on the lake and a delicious meal at the same time. And the great news is that there’s plenty of choices too from brunch to lunch to dinner. So, sit back and chill out as you cruise past some of the Windy City’s towering buildings and spectacular waterfront.
Millennium Park
Millennium Park is the city’s best place to kick back outdoors. Covering an impressive 24.5 acres, the park is home to some of Chicago’s most famed attractions including Cloud Gate (a.k.a. The Bean) as well as Crown Fountain. You can even take your sightseeing up a level with Virgin Experience Gifts’ architecture and highlights tour around the city led by an experienced and entertaining local guide.
Driving Experiences
For a completely unique and one hundred percent thrilling activity, check out one of Virgin Experience Gifts’ Chicago Driving Experiences. Get behind the wheel of your dream car at a world-class racecourse or leave it to the experts and enjoy a high-speed passenger ride for the driving adventure of a lifetime.
Navy Pier
Often called the People’s Pier, Navy Pier is one of Chicago’s main attractions. Housing a 200 foot Ferris wheel, museums, theaters and more, the sheer amount of things to do on the pier warrants spending a day or two here.
Flying Experiences
Explore the Windy City from sky-high with one of our epic flying experiences. Ranging from helicopter lessons to hot air balloons and beyond, soar over skyscrapers and check something off the bucket list while you’re in the city. If you need some more inspiration, we recommend indoor skydiving. Feel the adrenaline rush of floating, flying and free-falling from a clear safe indoor wind tunnel.
Wrigley Field
Home to the Chicago Cubs, Wrigley Field is the second-oldest Major League baseball park in the US. Known for its unique traditions and charm, it’s definitely worth trying to catch a game of baseball while you’re in town. Alternatively, ballpark tours offer an insider’s look into the legendary 100 year history of this popular attraction.
Murder Mystery Dinner
Do dinner out a bit differently. Satisfy your inner crime-lovers as you enjoy an electrifying murder mystery dinner with America’s most popular interactive dinner theater company. Enjoy an elegant four-course meal immersing yourselves in a modern-day mystery, following leads and investigating clues to figure out whodunnit. Remember – everyone is a suspect…even you!
Willis Tower
In the heart of downtown Chicago lies the famed Willis Tower. Standing proud at 110 stories, the tower is one of the tallest buildings in the world and second in North America. On a clear day, views can span 50 miles and thrill-seekers can get even closer to the action with the Skydeck and Ledge which sits 103 stories up.
Beer Spa Session
The Windy City is not short of one-of-a-kind experiences and a beer spa day is just that. Take a break from sightseeing with a 75 minute session discovering the rejuvenating power of beer, the calming benefits of sauna steaming and float in a cedar tub filled with a restorative infusion.
The Magnificent Mile
The Magnificent Mile draws millions of visitors and shopaholics every year. Featuring numerous galleries, boutiques and flagship stores, the district is one of Chicago’s most thriving. The Mile is also in the heart of the city’s famous culinary scene offering a delectable spread of eateries.
Kayak Tours
For avid paddling enthusiasts, Chicago is brimming with places to kayak that offer a unique perspective of the city’s skyline and surrounding nature areas. With a variety of themed tours on offer from architectural to sunset, they’re a sure-fire way to see the city like you’ve never seen it before.
Lincoln Park Zoo
Home to more than 1,000 animals, the 35-acre Lincoln Zoo is consistently top of visitors’ to do lists in Chicago. Completely free to enter, the zoo is always acquiring new residents meaning you’re likely to spot some cute baby animals when you visit. There’s numerous events that take place throughout the year including wine festivals, craft brews and kid singalongs.
Outdoor Scavenger Hunt
Sure, you could just go to the attractions but isn’t it more fun to uncover them as part of a treasure hunt? Explore the city’s fascinating artwork and architecture in an entirely new way with an app-lead scavenger hunt. Across 14 different challenges, stroll through Chicago’s streets and marvel at the famed landmarks like Millennium Park along the way.
Art Institute of Chicago
Truly world-class, the institute displays more than 300,000 pieces of artwork, covering a variety of mediums from paint to photography to sculpture. The institute is most well-known for its exhibitions of Georges Seurat's 1884 A Sunday Afternoon on La Grande Jatte and Renoir's 1879 Acrobats at the Cirque Fernando.
Food Tours
For many folks, the way to their heart is through the stomach so no to-do list is complete without at least one food activity. Discover decadent foods, desserts and beverages with a food tour strolling through the streets of Chicago. Of course, you can’t talk about the Windy City’s culinary scene without mentioning their famed specialty; the deep pan pizza tour will highlight the places that played a key role in the growth of Chicago’s deep pan reputation.
Music Box Theater
To get your fix of timeless Hollywood blockbusters, head to the Music Box Theater. The two-screen cinema shows the latest indie productions, regularly hosts director Q&As and serves traditional movie snacks like popcorn with butter.
Golf
Considered by many to be the metropolitan golf mecca of the Midwest, it’s hardly surprising that there’s an array of golfing days out in Chicago. Whether you’re a pro on the green or just a pro at watching Tiger Woods tee off on TV, spending the day at one of Chicago’s finest golf courses is always a good idea. You can even sharpen your swing with a golf lesson from a PGA Pro covering expert tips and techniques to help you gain confidence on the green.
Shedd Aquarium
If Lake Michigan’s got you thinking about underwater worlds, you’ll want to head on over to the Shedd Aquarium. Inside, you’ll discover thousands of aquatic creatures that reside here from all over the world including penguins, sharks and a Giant Pacific Octopus.
Helicopter Tours
Put a new spin on the best things to do in Chicago and scope out famed landmarks and favorite sights from above with a helicopter tour. This fun sky-high adventure will typically take you on a 30-to-45 minute ride past The Windy City’s attractions like Wrigley Field, Millennium Park and Navy Pier.
The Chicago Riverwalk
The Riverwalk provides pedestrianized access along Chicago’s picturesque waterfront. The trail is lined with restaurants, bars and offers a picture-perfect perspective of the city’s dazzling skyline.
Date Night Collection
Spending quality time with your partner is always a good idea and that’s where Virgin Experience Gifts’ comes in with a curated Chicago Date Night Collection. The types of date night activities are almost endless. Go kayaking, feel the adrenaline rush of indoor skydiving, enjoy a private art lesson or one of the many tours: food, brews, bikes and more.
Garfield Park Conservatory
One of the largest greenhouses in the US, Garfield Park Conservatory is home to around 600 plants. Marvel at the huge trees in the Palm Room or visualize what Illinois looked like back in the day in the Fern Room.
Guided Bike Tours
If you want to sightsee in style, you’ll definitely want to check out the range of Chicago Bike Tours. Pedal a cool, cruiser bike as you hit the city’s main attractions on two wheels. Along the way, a guide will entertain you with funny stories and little-known facts.
Adler Planetarium
The first of its kind in America, the Adler Planetarium built in 1930 is a building dedicated to the study of astronomy and astrophysics. From inside the prominent dome, you can travel through the universe in a state-of-the-art digital projection. Outdoor highlights include the Skyline Walk with some of the best views in Chicago.
The Green Mill
Bust out the trendiest threads you own and make your way over to The Green Mill. Slinging drinks since before The Prohibition, The Green Mill is a popular fixture on Chicago’s live jazz scene. Grab a selfie outside the iconic marquee before dancing the night away with plenty of tasty cocktails.
The things to do in Chicago don’t stop there! For more fun outings, don’t miss the full range of experiences in the Windy City here.
