Chicago Attractions and Things to Do

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Select Your Chicago Experience:

360 CHICAGO

Chicago

Get ready for an unforgettable experience at the 360 Chicago Observation Deck, located on the 94th floor of 875 North Michigan Avenue (John Hancock Center)! With 360 Chicago tickets, soak in breathtaking panoramic views of the Windy City and Lake Michigan from 1,000 feet above the Magnificent Mile. Elevate your Chicago trip with this must-see attraction! Details

20 Reviews

$26.79

Total Price: $30.00 (USD)

Medieval Times Dinner and Tournament Illinois

Medieval Times Dinner and Tournament Chicago/Schaumburg Castle • Schaumburg

One of the country’s longest-running dinner attractions, Medieval Times Dinner and Tournament Chicago offers a fun and exciting way to enjoy a feast with family or friends. Enjoy a banquet-style four-course feast without utensils while watching six brave knights compete in skill games atop spirited Andalusian stallions. Details

1051 Reviews

$76.95 $66.95

Total Price: $73.88 (USD)

You Save: $10.00

Architecture River Tour from Navy Pier

Shoreline Sightseeing • Chicago

Step aboard the Shoreline Architecture River Cruise from Navy Pier and discover the magic of the Windy City's architectural wonders! Glide past over 40 iconic buildings, from the majestic John Hancock Center to the historic Wrigley Building, as your expert guide provides detailed descriptions. Kids age 2 and under are free, and the tour is dog-friendly, too. Details

2 Reviews

$39.00

Total Price: $39.00 (USD)

Go City Chicago Explorer Pass

Go City Chicago • Chicago

The Chicago Explorer Pass by Go City is an affordable and convenient way to see the best of Chicago. Choose from over 30 top attractions, including Skydeck Chicago, Adler Planetarium, and Field Museum. Enjoy flexibility and savings as you explore at your own pace. Perfect for travelers looking to see more while spending less! Details

2 Reviews

$84.00 $79.06

Total Price: $79.06 (USD)

You Save: $4.94

Chicago Crime Tours

Chicago Crime Tours and Experiences LLC • Chicago

Discover the Windy City's dark history with Chicago Crime Tours. This 1.5 to 2-hour experience takes you to infamous crime scenes like the Biograph Theatre, Clark Street Bridge, and Holy Name Cathedral. Hear gripping tales of Al Capone, John Dillinger, Thomas "Terrible Tommy" O'Connor, and more—all from the comfort of a climate-controlled sightseeing bus. Details

3003 Reviews

$42.00

Total Price: $46.84 (USD)

LEGOLAND Discovery Center Chicago

Schaumburg

Unleash your imagination at LEGOLAND Discovery Center Chicago, where interactive exhibits, themed rides, and millions of LEGO bricks await. Explore MINILAND®, build and race creations, and enjoy 4D cinema adventures—perfect family fun for LEGO fans of all ages. Details

1610 Reviews

$24.99

Total Price: $26.19 (USD)

iFLY Indoor Skydiving - Chicago Lincoln Park

iFLY Indoor Skydiving - Chicago Lincoln Park • Chicago

Located just minutes from the Lincoln Park Conservatory and Old Town Triangle, iFLY Indoor Skydiving Chicago Lincoln Park offers the rush of free-falling in a safe and controlled environment—no airplane or parachute needed. Whether you are a first-timer or a seasoned flyer, expert instructors will guide you through an unforgettable adventure. Come fly today! Details

148 Reviews

$125.00

Total Price: $135.88 (USD)

Art Institute of Chicago Skip-the-Line Guided Tour

Babylon Travel & Tour Services • Chicago

Bypass the wait with a skip-the-line guided tour of the Art Institute of Chicago. Immerse yourself in a world-class collection, featuring Impressionist and modern masterpieces, such as Sunday on La Grande Jatte by Georges Seurat and Nighthawks by Edward Hopper. Let an expert guide reveal the stories behind both iconic artworks and lesser-known treasures. Details

42 Reviews

$85.00 $81.00

Total Price: $81.00 (USD)

You Save: $4.00

Flyover in Chicago

Chicago

Flyover Chicago tickets give you access to an immersive flight experience at Navy Pier, featuring motion seat technology, a 65-foot spherical screen, and a soaring musical score enhanced by scents and mists that make Chicago's skyline and lakefront feel vividly real. Details

$33.95 $31.95

Total Price: $35.70 (USD)

You Save: $2.00

Chicago River Architecture Tour

Wendella Tours & Cruises • Chicago

This Chicago architecture boat tour by Wendella showcases over 50 architectural landmarks like Marina City and Willis Tower in 45- or 90-minute options. Enjoy narrated skyline views from open-air decks or climate-controlled interiors. Each cruise blends history, design, and unforgettable riverfront perspectives. Details

132 Reviews

$28.00 $26.00

Total Price: $26.00 (USD)

You Save: $2.00

Go City Chicago All-Inclusive Pass

Go City Chicago • Chicago

Discover as many sites as you can with the All-Inclusive Chicago Pass by Go City. With access to over 40 attractions, you can enjoy a variety of experiences for guests of all ages and interests, including museum admission, theater tours, and sightseeing trips. Save money and plan your adventure through Chicago’s urban jungle with this one-of-a-kind passport! Details

1 Reviews

$149.00

Total Price: $149.00 (USD)

Medieval Torture Museum Chicago

Chicago

Visit Medieval Torture Museum Chicago and discover the most extensive Middle Ages torture exhibits in the U.S. Located in the Chicago Loop, explore the interactive museum’s elaborate torture devices and realistic execution depictions that are not for the faint of heart! Do you have the courage to endure a visit to the horrifying evidence of human cruelty? Details

1249 Reviews

$37.45 $35.83

Total Price: $39.96 (USD)

You Save: $1.62

Chicago's Chinatown Food and Walking Tour

Bobby's Bike Hike - Chicago Bike, Walking & Food Tours • Chicago

Celebrate the city’s vibrant Chinese heritage on a Chinatown food tour in Chicago, savoring dim sum, noodles, and regional specialties. Discover the neighborhood’s rich cultural history while sampling local favorites at hidden-gem restaurants in Chinatown Square and along Wentworth Avenue. Details

4774 Reviews

$79.99 $69.99

Total Price: $69.99 (USD)

You Save: $10.00

Architecture River Tour from Michigan Avenue

Shoreline Sightseeing • Chicago

The 75-minute Shoreline Sightseeing Architecture River Tour from Michigan Avenue departs near the Magnificent Mile for a cruise through all three branches of the Chicago River. Pass 40+ landmarks, including the John Hancock Center and Wrigley Building, while expert guides share the architects, engineering breakthroughs, and designs behind Chicago's skyline. Details

2 Reviews

$46.00

Total Price: $46.00 (USD)

Big Bus Tours Chicago

Big Bus Tours Chicago • Chicago

Take in Chicago’s skyline from an open-top double-decker bus. Big Bus Tours Chicago makes sightseeing effortless with a hop-on, hop-off service. See famous landmarks like Millennium Park, Willis Tower, and Navy Pier while learning from insightful commentary. Ride at your own pace, capturing stunning views with convenient stops near top attractions. Details

1 Reviews

$49.00

Total Price: $49.00 (USD)

Chicago by Night: 90 Minute River and Lakefront Cruise

First Lady • Chicago

Take in sweeping views of Chicago’s skyline from the water on the Chicago by Night Cruise. As you glide along the Chicago River and the Lake Michigan shoreline, a knowledgeable guide shares insights into the city’s architecture, history, and cultural landmarks. Watch as the skyline lights up at dusk, offering a striking and memorable perspective of the city. Details

1 Reviews

$50.00 $45.00

Total Price: $45.00 (USD)

You Save: $5.00

Chicago Favorites Food and Walking Tour

Bobby's Bike Hike - Chicago Bike, Walking & Food Tours • Chicago

Sample some of Chicago's famous dishes on the Chicago Favorites Ultimate Food & Walking Tour. Indulge in deep-dish pizza, the original chocolate brownie, and local craft beers. Visit some of the most renowned restaurants and bars in the city. Along the way, you’ll come across Chicago’s landmarks, well-known neighborhoods, and historic spots. Details

4770 Reviews

$79.99 $72.99

Total Price: $80.36 (USD)

You Save: $7.00

iFLY Indoor Skydiving - Chicago Naperville

iFLY Indoor Skydiving - Chicago Naperville • Naperville

Located minutes from The Morton Arboretum and Arrowhead Country Club, iFLY Naperville offers the ultimate indoor skydiving experience for adventurers of all ages. Soar in a state-of-the-art wind tunnel with expert instructors guiding each flight. No experience necessary—just bring your sense of adventure and prepare for a flight experience of a lifetime. Details

279 Reviews

$125.00

Total Price: $125.00 (USD)

iFLY Indoor Skydiving - Chicago Rosemont

iFLY Indoor Skydiving - Chicago Rosemont • Chicago

Just minutes from O’Hare International Airport and Fashion Outlets of Chicago, iFLY Rosemont offers a thrilling indoor skydiving experience for first-timers and seasoned pros alike. Enjoy a 1.5-hour flying experience in a state-of-the-art vertical wind tunnel, no parachute needed. Let your dreams take flight at iFLY Indoor Skydiving - Chicago Rosemont! Details

381 Reviews

$125.00

Total Price: $131.02 (USD)

American Writers Museum

Chicago

In the heart of downtown Chicago, the Writers Museum on Michigan Avenue walks you through centuries of American history and culture from the writers' perspective. The American Writers Museum-Chicago is the only museum devoted to diverse US writers and writings, with fun multi-sensory exhibits to celebrate the past and promote the future of American literature! Details

453 Reviews

$16.00 $14.00

Total Price: $14.28 (USD)

You Save: $2.00

Bikes, Bites, & Brews - Chicago's Signature Dishes Bike Tour

Bobby's Bike Hike - Chicago Bike, Walking & Food Tours • Chicago

Hop on your bike and get ready for a tasty tour through Chicago’s most diverse and delicious neighborhoods. You’ll stop at local eateries loved by locals all while learning about Chicago’s history, notable landmarks, and restaurants. This four-hour tour includes all food and beverages, along with bikes to ride if you don’t have one. Details

4775 Reviews

$89.99 $81.99

Total Price: $90.27 (USD)

You Save: $8.00

Canine Cruise on Chicago's First Lady

First Lady • Chicago

Sail with your pup on the 90-minute, dog-friendly Canine Cruise through the Chicago River and Lake Michigan. Take in skyline views, live architectural commentary, and thoughtful amenities for both dogs and their humans. It's one of the most unique and pet-friendly things to do in Chicago. Details

478 Reviews

$46.00 $41.00

Total Price: $41.00 (USD)

You Save: $5.00

Chicago 3D Fireworks Cruise

First Lady • Chicago

Hop aboard the Chicago fireworks cruise on Lake Michigan and watch the night sky light up in 3D. Departing from the Chicago Riverwalk, take in the panoramic skyline views from the open-air deck with lively narration on the way to the Harbor Lock. Then, enjoy a spectacular fireworks show enhanced with complimentary 3D glasses and synchronized music. Details

1 Reviews

$52.00 $48.00

Total Price: $48.00 (USD)

You Save: $4.00

Chicago Premier Dinner Cruise on Lake Michigan

City Cruises Chicago Navy Pier • Chicago

Indulge in a premier Chicago dinner cruise aboard Odyssey Lake Michigan. Departing from Navy Pier, pass by iconic landmarks such as Willis Tower, Adler Planetarium, and more. Whether celebrating a special occasion or simply looking for a unique dining experience, this dinner cruise in Chicago offers an unforgettable evening of elegance and fine dining. Details

$144.90

Total Price: $199.67 (USD)

Chicago's Lakefront Neighborhoods Bicycle Tour

Bobby's Bike Hike - Chicago Bike, Walking & Food Tours • Chicago

This award-winning Chicago bike tour takes you through vibrant neighborhoods and along the scenic Lakefront Trail. Explore Lincoln Park, Old Town, and the Gold Coast with a local guide. Bikes and helmets are included, with photo stops at some of the city's most iconic views. Details

4775 Reviews

$54.99 $49.99

Total Price: $55.04 (USD)

You Save: $5.00

Chicago's Ultimate City Bike Tour

Bobby's Bike Hike - Chicago Bike, Walking & Food Tours • Chicago

Explore Chicago's iconic landmarks on a three-hour guided bike tour with Bobby's Bike Hike. Enjoy a leisurely nine-mile ride along the Lakefront Trail, visiting sites like Museum Campus, Millennium Park, and more. Perfect for all fitness levels. Details

4774 Reviews

$54.99 $50.99

Total Price: $56.12 (USD)

You Save: $4.00

First Lady Sightseeing Cruise: Chicago River & Lake

First Lady • Chicago

Explore Chicago’s skyline and landmarks on a 90-minute guided river and lake cruise aboard the First Lady. Enjoy expert commentary on architectural icons like Willis Tower, Tribune Tower, and the Wrigley Building. This family-friendly cruise offers stunning views and insights into the city’s rich history and design legacy. Details

1 Reviews

$46.00 $42.00

Total Price: $42.00 (USD)

You Save: $4.00

Lake and River Architecture Boat Tour

Wendella Tours & Cruises • Chicago

Wendella's Chicago Lake and River Architecture Tour offers expert narration and skyline views from both the river and Lake Michigan. Cruise past more than 50 landmarks along the river, then pass through the Chicago Lock into Lake Michigan for panoramic views stretching from Navy Pier to Grant Park. Details

$45.00 $41.00

Total Price: $41.00 (USD)

You Save: $4.00

Night Crime Tours

Chicago Crime Tours and Experiences LLC • Chicago

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

2995 Reviews

$47.00

Total Price: $52.41 (USD)

Skyline Lake Tour

Shoreline Sightseeing • Chicago

Take in Chicago's skyline from the open waters of Lake Michigan on this 30-minute Chicago skyline lake tour from Navy Pier. Cruise past iconic landmarks like Willis Tower, Aqua Tower, and the Chicago Harbor Lighthouse as pre-recorded commentary shares the story behind the city's architecture. Details

$32.50

Total Price: $32.50 (USD)

Spirit of Chicago Lunch Cruise on Lake Michigan

City Cruises Chicago Navy Pier • Chicago

Set sail on a Chicago lunch cruise for a casual day out on Lake Michigan aboard the Spirit of Chicago. Departing from the iconic Navy Pier, the cruise will pass by iconic landmarks such as the Willis Tower and Adler Planetarium. Feast on a delectable chef-prepared lunch buffet while enjoying stunning views of the Chicago skyline and onboard entertainment. Details

1 Reviews

$91.90

Total Price: $126.64 (USD)

The Chicago Theatre Tour Experience

Chicago

Step into the spotlight with The Chicago Theatre Tour! Marvel at the French Baroque-style architecture, walk the iconic stage, and explore behind-the-scenes areas where entertainment legends like Frank Sinatra and Dolly Parton once stood. From the grand lobby to the Wurlitzer organ, every corner tells a story of Chicago's rich cultural history. Details

$27.95 $24.06

Total Price: $26.42 (USD)

You Save: $3.89

Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck

Travel Curious • Chicago

See Chicago from the ground up and from way up high on this private Chicago walking tour! Discover more about The Windy City while taking advantage of all the city has to offer– including the expansive trails of Millennium Park, the opulent stores on Magnificent Mile, unique art and architecture that defines the city, and a stunning view of the Chicago skyline. Details

1 Reviews

$411.00

Total Price: $419.22 (USD)

Discover the Best Things to Do in Chicago

Visiting the Windy City offers a wide range of things to do in Chicago. You can explore vibrant, diverse neighborhoods, each with a distinct character and cultural background. As a result, the possibilities feel nearly endless.

Whether you visit in summer or winter, Chicago offers something for every interest. In other words, the city’s versatility makes it a destination for everyone.

Experience Chicago’s Music and Architecture

Award-winning jazz and blues are an integral part of Chicago’s soul. Even without seeking them out, street musicians often fill the air with melodies that capture the city’s spirit.

If architecture piques your interest, take an enlightening walking tour through the city. There, the blend of historic and modern buildings showcases Chicago’s evolution over time.

Enjoy Sports, Lakefront Views, and Local Flavor

Sports enthusiasts will feel right at home in Chicago. For example, you can cheer on the Cubs at Wrigley Field or support the Bulls and Blackhawks at the United Center. Meanwhile, sailing on Lake Michigan offers a different kind of thrill, with the city skyline as your backdrop.

No list of Chicago things to do feels complete without its renowned culinary scene. From famous deep-dish pizza to a wide range of global cuisines, the city gives your taste buds plenty to enjoy.

At the same time, Chicago’s art scene stands out for those who love visual storytelling. Because of this variety, the city blends creativity, culture, and flavor in every neighborhood.

Top Things to Do in Chicago

Explore the city’s diverse neighborhoods, each with a distinct character.
Indulge in iconic culinary delights, including famous deep-dish pizza.
Join the vibrant sports scene, from baseball games to sailing adventures.
Take an architectural tour that highlights Chicago’s dynamic evolution.

Embrace Chicago’s tempting allure through its music, architecture, cuisine, sports, and art. Altogether, these experiences define the authentic things to do in Chicago.

Unlock Your Chicago Adventure Today with Tripster's Unbeatable Experiences!

Do not wait another moment. Start creating your unforgettable Chicago adventure today with Tripster. From thrilling sports games and arts performances to serene parks and historic sites, so much awaits your discovery.

Immerse yourself in the heart of American culture and excitement, all at unbeatable prices. Book your tickets now through Tripster and make the most of your next trip. After all, a Chicago experience is more than a journey; it is a treasure trove of memories waiting to be made.

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Chicago Things to Do

Select Your Chicago Experience:

360 CHICAGO

Medieval Times Dinner and Tournament Illinois

Architecture River Tour from Navy Pier

Go City Chicago Explorer Pass

Chicago Crime Tours

LEGOLAND Discovery Center Chicago

iFLY Indoor Skydiving - Chicago Lincoln Park

Art Institute of Chicago Skip-the-Line Guided Tour

Flyover in Chicago

Chicago River Architecture Tour

Go City Chicago All-Inclusive Pass

Medieval Torture Museum Chicago

Chicago's Chinatown Food and Walking Tour

Architecture River Tour from Michigan Avenue

Big Bus Tours Chicago

Chicago by Night: 90 Minute River and Lakefront Cruise

Chicago Favorites Food and Walking Tour

iFLY Indoor Skydiving - Chicago Naperville

iFLY Indoor Skydiving - Chicago Rosemont

American Writers Museum

Bikes, Bites, & Brews - Chicago's Signature Dishes Bike Tour

Canine Cruise on Chicago's First Lady

Chicago 3D Fireworks Cruise

Chicago Premier Dinner Cruise on Lake Michigan

Chicago's Lakefront Neighborhoods Bicycle Tour

Chicago's Ultimate City Bike Tour

First Lady Sightseeing Cruise: Chicago River & Lake

Lake and River Architecture Boat Tour

Night Crime Tours

Skyline Lake Tour

Spirit of Chicago Lunch Cruise on Lake Michigan

The Chicago Theatre Tour Experience

Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck

Discover the Best Things to Do in Chicago

Experience Chicago’s Music and Architecture

Enjoy Sports, Lakefront Views, and Local Flavor

Top Things to Do in Chicago

Unlock Your Chicago Adventure Today with Tripster's Unbeatable Experiences!