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Climb aboard a state-of-the-art helicopter and get ready to see the Windy City from an entirely new perspective. Soar high above the city in a daytime, evening, or twilight tour for remarkable views of the Chicago cityscape. Watch the city shine below while you learn about city landmarks, history, notable events, and more. Details
TripAdvisor user rating 4.50 out of 5
484 Reviews
$189.99 $180.49
You Save: $9.50

Art Institute of Chicago

Downtown, Chicago
Boasting more than 1.5 million local, national, and international visitors a year, the Art Institute of Chicago is a must-see destination. Located at 111 South Michigan Avenue in the World’s Fair Building, the Art Institute is home to a world-class collection of fine art ranging from contemporary pieces to historic works of art such as Pablo Picasso’s, “The Old Guitarist” and Grant Wood’s, “American Gothic.” Details
TripAdvisor user rating 5.00 out of 5
24004 Reviews
$35.00

Skydeck Chicago

Downtown, Chicago
Located on the 103rd floor of the former Sears Tower, Skydeck Chicago offers a unique way to see The Windy City and beyond from a jaw-dropping 1,353 feet in the air. Open 365 days a year, this exciting attraction also offers museum-quality exhibits, a fascinating theater presentation and more. Guests can step out on The Ledge’s glass boxes, which extend about 4.3 feet from the Skydeck. Details
TripAdvisor user rating 4.50 out of 5
17439 Reviews
$26.00 $21.00
You Save: $5.00
Immerse your family into one-of-a-kind LEGO® exhibits, rides, 4D theaters, and so much more at the LEGOLAND® Discovery Center in Chicago. Tour the LEGO® factory, ask a pro builder all of your questions, and build to your heart’s desire! From the DUPLO Village to MINILAND Chicago, there’s so much to explore. With 11+ attractions to enjoy, it’s fun for the whole family. Details
TripAdvisor user rating 3.50 out of 5
1524 Reviews
$24.95 $19.95
You Save: $5.00
An unforgettable dining cruise over Lake Michigan, Chicago Odyssey offers a scenic escape from land to see The Windy City’s breathtaking skyline from the sea. Guests can enjoy all that the ship has to offer, including three climate-controlled decks with a dance floor and LED lighting, a wide range of wine and microbrew selections, a delicious dinner, and a rooftop lounge with modern furniture. Details
TripAdvisor user rating 4.50 out of 5
34 Reviews
$88.26 $77.22
You Save: $11.04
Chicago Crime Tours offer luxurious 90-minute tours of the Windy City, revealing some of its darker history of infamous criminals and gangsters. Guests can ride comfortably in a luxury, climate-controlled bus while learning about Al Capone, John Dillinger, Terrible Tommy, and more, while seeing famous crime scenes, like the Biograph Theatre, Clark Street Bridge, Holy Name Cathedral and more. Details
TripAdvisor user rating 4.50 out of 5
1057 Reviews
$36.24

Tall Ship Windy

Chicago, Northern Illinois
One of the best ways to see Lake Michigan and the Chicago city skyline, Tall Ship Windy takes guests on a leisurely cruise on the water. Sailing from the Navy Pier, guests can anticipate breathtaking views on the 148-foot traditional four-masted gaff topsail schooner. With three spacious decks with seating, passengers can sit back, relax, and take in the views on this 75-minute tour. Details
TripAdvisor user rating 4.50 out of 5
1315 Reviews
$37.00
Offered by Spirit Cruises, the Spirit of Chicago features a breathtaking experience for guests to view the beautiful Chicago skyline while dining, drinking and dancing at sea. The cruise ship provides a rooftop lounge, three climate-controlled interior decks with stunning panoramic windows, a live DJ and spacious dance floors, full-service bars and a delicious meal fit for any palate. Details
TripAdvisor user rating 4.00 out of 5
441 Reviews
$81.46

Best of Chicago - Grand Tour

Gray Line Chicago • Chicago, Northern Illinois
Best of Chicago - Grand Tour

This is a comprehensive tour of everything Chicago has to offer. Travel through both the North Side and South Side business and residential districts. All the points of interest covered in the North Side and South Shore tours are included in the Grand Tour. Details
TripAdvisor user rating 3.00 out of 5
276 Reviews
$52.95

Chicago Day Bike Tours

Fat Tire Tours • Chicago, Northern Illinois
Hop on a bike and pedal from Grant Street to Lincoln Park! This tour takes you through eight prestigious neighborhoods and makes numerous stops for incredible photo opportunities. You will hear the history of Chicago from a knowledgeable guide as you appreciate the stunning city architecture and beautiful lakefront. This tour is a fantastic way to see Chicago’s most famous sites! Details
TripAdvisor user rating 5.00 out of 5
14 Reviews
$42.51

Chicago Evening Segway Tour

City Segway Tours • Chicago, Northern Illinois
Enjoy the thrill of riding a Segway while observing the beautiful sunset over Chicago’s most famous sites including Grant Park, Buckingham Fountain, Lake Michigan Lakefront. and the Museum Campus. A knowledgeable guide will keep you on your toes with fun facts and history along the way. The city skyline at nightfall is truly a spectacle to behold! This experience is a great way to spend an evening with friends and family. Details
TripAdvisor user rating 5.00 out of 5
925 Reviews
$70.85

Chicago Fireworks Segway Tour

City Segway Tours • Chicago, Northern Illinois
Hop on a Segway and glide to an exclusive viewing location for the Navy Pier's famous evening fireworks show. Not only will you beat the crowds and have a perfect vantage point, but you will also get a sightseeing experience on the way. Visit Buckingham Fountain, the Lake Michigan Lakefront, Monroe Harbor, and many other famous sites. Once the show is over, your guide can help you find the perfect nightcap. Details
TripAdvisor user rating 5.00 out of 5
925 Reviews
$76.30

Chicago Sunset Bike Tour

Fat Tire Tours • Chicago, Northern Illinois
Enjoy a leisurely bike ride through the city as the daylight dips below the horizon on the Chicago Sunset Bike Tour! You will see iconic sites like never before as beautiful setting rays create a colorful display of light. This sightseeing experience offers incredible Skyline views and visits many hidden gems of the city. Riding a bike is the most pleasant way to travel around Chicago and is fun for all ages! Details
TripAdvisor user rating 5.00 out of 5
14 Reviews
$42.51

Historic Chicago - South Side Tour

Gray Line Chicago • Chicago, Northern Illinois
Historic Chicago - South Side Tour

This land tour will take you past all the sights of Chicago’s Historic South Side. You will head south out of the Loop down Michigan Avenue past Art Institute of Chicago, the starting point of historic Route 66, Grant Park, and the site of Chess Records. Your journey will continue along Lake Michigan on South Lake Shore Drive. Traveling on, you will see President Obama’s home, Robie House, University of Chicago and Jackson Park, and the Museum of Science & Industry. The return trip will take you through Museum Campus and past Buckingham Fountain. Details
TripAdvisor user rating 3.00 out of 5
276 Reviews
$34.95
Step into the lives of Chicago’s most notorious criminals as you embark on this nighttime tour. From the comfort of an air-conditioned bus, you’ll encounter iconic crime scenes and historic bars. Drinks are not included. On this 2.5-hour luxury bus tour through the streets of Chicago, you’ll learn about everything from the legendary Al Capone to the St. Valentine’s Day Massacre. Details
TripAdvisor user rating 4.50 out of 5
1057 Reviews
$40.82

Odyssey Chicago River

Entertainment Cruises • Chicago, Northern Illinois
Enjoy a delicious multi-course meal made from fresh ingredients as you sail the beautiful Odyssey Chicago River! See the city's most iconic buildings, and learn fun facts and history along the way. If you want a luxurious Chicago journey that is both entertaining and relaxing, this cruise is for you! With brunch, lunch, and dinner cruises available, you can choose the itinerary that works best for your schedule. Details
TripAdvisor user rating 5.00 out of 5
68 Reviews
$122.26 $106.98
You Save: $15.28
Scenic Chicago - North Side Tour

This is the tour for those looking to experience the vitality and excitement of Chicago! You'll drive through Chicago's main business section, one of the busiest financial centers in the world. You'll tour the famous "Loop" and State Street - the great street where Chicago's fame began. Next, travel by the striking Richard J. Daley Plaza with its acknowledged masterpiece, the Pablo Picasso sculpture, created specifically for Chicago. You will take a ride on Wacker Drive, the double-decked thoroughfare that winds its way under the city. Also, journey over the Chicago River, which flows backward due to one of the world's greatest engineering feats.

On this tour, you'll see the famous white Wrigley Building that announces the beginning of the Magnificent Mile and Michigan Avenue, where Chicago's most exclusive stores exhibit their wares. You'll see Chicago's elegant seven-level shopping complex, the renowned Water Tower Place, alongside one of the tallest buildings in the world, the John Hancock Center. You will also travel through Lincoln Park, a thousand acres of greenery, lagoons, flowers, and zoo. You'll see Wrigley Field - the home of the Cubs (visits not on game days), the Botanical Gardens, Chicago Historical Society, Newberry Reference Library, and an Indian Totem Pole. Also, enjoy a twenty minute stop at the Lincoln Park Conservatory.

If you're looking for a day of adventure in Chicago, then this is the tour for you! Details
TripAdvisor user rating 3.00 out of 5
276 Reviews
$34.95

The Escape Game Chicago

Chicago, Northern Illinois
You’re trapped in a room with your closest friends and family. There’s 60 minutes on the clock and a world of puzzles to solve before you can escape. Do you think your group can band together to beat the clock? At Escape Game Chicago, you can choose from different themed rooms including a heist scenario and a jailbreak. Use your teamwork and communication skills to beat the challenges and escape! Details
TripAdvisor user rating 5.00 out of 5
2566 Reviews
$35.99 $33.99
You Save: $2.00

Two Hour Chicago Segway Tour

City Segway Tours • Chicago, Northern Illinois
Segway is the newest trend when it comes to touring because you can cover more ground. Plus, it’s just plain fun! You will have numerous Instagram-worthy photo opportunities as you travel to the best spots in Chi-Town including Grant Park, Buckingham Fountain, the Crown Fountain, and so much more! Your knowledgeable guide will reveal interesting facts and history of Chicago along the way. Details
TripAdvisor user rating 5.00 out of 5
925 Reviews
$70.85