All Chicago Tours &amp; Excursions in 2026 - page 16

Chicago Bears Football Game at Soldier Field

4 hours

from $4,958

Elevate your travel experience in Chicago with luxurious limousine transfers that redefine comfort and sophistication. Whether it’s a corporate event, wedding, or a night out, each ride offers plush interiors and exceptional service from professionally trained chauffeurs. Enjoy complimentary bottled water as you glide through the city in style, taking in the vibrant urban landscape. With options ranging from sedans to spacious SUVs, every detail is catered to ensure your journey is seamless and memorable. - Premium vehicles including Cadillac and Mercedes-Benz options - Professional chauffeurs familiar with the best routes - 24/7 service to accommodate your schedule - Group bookings available for larger parties or events

Luxury Limousine Transfers in Chicago

Free Cancellation
1 hour

from $180

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests enjoy a private ride through iconic neighborhoods and landmarks while learning about the city’s history, culture, and architecture at their own pace. Ideal for airport transfers, short stays, and first-time visitors seeking a relaxed yet memorable city experience

Chicago Exotic Auto Experience

3 to 7 hours

from $1,800

Take part in a unique evening Happy Hour Cruise, featuring fresh craft beers while cruising the stunning Chicago skyline. Every Thursday and Friday evening, this 2-hour experience begins on Lake Michigan, sails through the locks, and navigates the Chicago River, providing breathtaking views and delightful sunsets. On Thursdays, a representative from Phase Three Brewing will be onboard to share insights about their innovative ales and lagers, enhancing your tasting experience. On Fridays, we showcase live music. This cruise is exclusively for adults 21 and older, making it the perfect outing for beer enthusiasts looking to unwind in a vibrant setting. - Enjoy a 2-hour sunset cruise - Cruise through Lake Michigan and downtown Chicago's iconic skyline - Exclusively for adults 21 and over, ensuring a mature atmosphere

Happy Hour Fireboat Cruise

381

Free Cancellation
2 hours

from $80

Discover the wild heart of Chicago on our guided walking tour through Lincoln Park, where nature and history meet in one unforgettable experience. What sets our tour apart is the seamless blend of three iconic destinations—the Peggy Notebaert Nature Museum, the lush Lincoln Park Conservatory, and the vibrant Lincoln Park Zoo—curated into one dynamic, story-filled journey led by a knowledgeable local guide. You'll marvel at the butterflies in flight, wander through exotic gardens under glass, and encounter wildlife from around the world—all while uncovering the hidden history and surprising beauty of this beloved urban oasis. Whether you're a first-time visitor or a lifelong Chicagoan, this tour offers fresh insights, natural wonders, and photo-worthy moments at every turn. Book now and see why Lincoln Park is one of Chicago’s most treasured gems!

Lincoln Park Nature Museum & Zoo Private Walking Tour

5.0

(2)

Free Cancellation
2 hours

from $250

Logan Square Walking Tour Experience

Free Cancellation
1 hour 20 minutes

from $35

Likely to Sell Out

Chase away your Monday blues with Chicago’s coolest concert at sea! Hop aboard the historic Tall Ship Windy for a 2-hour live blues music cruise on Lake Michigan, featuring city skyline views and a rotating roster of top local and international artists. With a full-service bar and plenty of space to move, relax, and dance, this floating music event blends unbeatable atmosphere with legendary sounds—perfect for date nights, group outings, or music lovers looking for a summer highlight. VIP boarding upgrades and kid discounts available. Book early; these shows sell out fast!

Monday Night Concert Series: Blues and Views Aboard Tall Ship

1616

2 hours

from $81

Step into a world where every detail is curated for comfort, style, and precision. Our plush Sprinter vans offer spacious interiors, leather seating, ambient lighting, and onboard amenities that turn every ride into a first-class experience. Be greeted by VIP chauffeurs — professionally trained, impeccably dressed, and committed to delivering white-glove service from door to destination. Whether you're heading to a corporate engagement, private event, or weekend escape, our team ensures you arrive with confidence and grace. Enjoy seamless airport pickup with real-time flight tracking, curbside coordination, and zero wait time. From O’Hare to Midway and beyond, we make your arrival smooth, stress-free, and elevated.

Group Van Transfers from Chicago O'Hare and Midway Airports

Free Cancellation
1 to 2 hours

from $300

Skip the crowds this is a private tour for your group only! Embark on a captivating journey through Chicago’s most illustrious addresses, where each step tells a story of architectural brilliance, historical grandeur, and cultural allure. From the soaring heights of 1150 Lake Shore Drive to the opulent corridors of the Original Playboy Mansion, this tour invites you to delve into the heart of the city’s rich heritage. Discover hidden stories behind iconic facades, walk the paths of the influential, and immerse yourself in the elegance that has shaped Chicago. This isn’t just a tour; it’s your gateway to experiencing the soul of a city that prides itself on architectural marvels and legendary tales. Make history your playground and become the hero of your own Chicago adventure with us.

Likely to Sell Out

Echoes of Elegance Private Tour Chicago’s Architectural Splendors

Free Cancellation
2 hours

from $652

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent Mile—or dive deep into 1920s mobster hangouts and hidden Prairie Style masterpieces. Ask about literally anything that catches your eye—from a Gilded Age historic district to a secret jazz club or a towering steel-and-glass skyscraper. The Windy City's deepest secrets are entirely yours to uncover. Point & Discover: Snap a photo of any monument or museum masterpiece to instantly receive a captivating and accurate story. It’s like having a historian in your pocket! Ultimate Freedom: Navigate seamlessly with interactive map-based audio tours. Your schedule, your pace, your rules. Choose Your Vibe: Select a narrator persona that matches your style—from a deep-diving scholar to a fun companion for the kids. Get Started: 7 Days of Premium Access available instantly for iPhone and Android.

Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

5.0

(2)

Free Cancellation
7 days

from $12

This beginner-friendly chocolate class turns a classic confection into an approachable, rewarding skill. Led by Chef Janet, the experience focuses on teaching essential techniques while keeping the atmosphere relaxed and fun. You’ll learn how to temper chocolate correctly, experiment with popular fillings and use molds to create beautifully shaped treats. Chef Janet breaks everything down step by step, making the process easy to follow even if you’ve never worked with chocolate before. With plenty of tasting, hands-on practice and a supportive environment, this Chicago class is ideal for dessert lovers, curious home cooks or anyone looking for a creative night out that ends on a sweet note.

Fun Chocolate Making Class With a Local Chef in Chicago

Free Cancellation
2 hours

from $75

Discover Chicago’s infamous gangster past on a private, fully personalized tour through the city’s historic Prohibition-era streets. Travel in comfort with your English-speaking driver, who shares captivating stories about Al Capone, rival gangs, speakeasies, and legendary crime events of the 1920s and 1930s. Begin at Biograph Theater, where John Dillinger was shot, then visit the St. Valentine’s Day Massacre site, a pivotal moment in Al Capone’s rise. Explore Holy Name Cathedral, the Cook County Criminal Court Building, and Harry Caray’s Italian Steakhouse, all linked to Chicago’s mob history. Conclude in the Chicago Loop, uncovering hidden speakeasies and secret nightlife spots from the Prohibition era. With a flexible, door-to-door itinerary, this private tour offers an immersive, thrilling look into the city’s dramatic gangster history.

Chicago Gangsters and Prohibition Private History Tour

Free Cancellation
2 hours

from $114

Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods with personalized attention and insider knowledge. Enjoy a hassle-free day with transportation, tickets, and lunch included. Explore Millennium Park, Navy Pier, and more, with plenty of photo opportunities and fascinating stories. Book now for an unforgettable Chicago adventure!

Likely to Sell Out

Chicago Small Group City Tour

Free Cancellation
9 to 10 hours

from $415

Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration! Whether you’re collaborating with your crew or turning up the competition, Let’s Roam Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza. Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll! With Let’s Roam, every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure!

A Spectacular Scavenger Hunts Chicago Adventure

Free Cancellation
1 hour 30 minutes

from $15

2 hours Private Evening Walking Tour with the Ghosts of Chicago

Free Cancellation
2 hours

from $350

Considered Chicago’s original “Millionaire’s Row,” Prairie Avenue in the Near South Side is renowned for its Gilded Age mansions—and this tour makes exploring easy (and delightfully spooky). In the evening, meet your guide in front of the Glessner House, and set off with ghost-hunting gear to accompany you. In between spotting highlights including the Marshall Field Jr. Mansion and the Henry B. Clarke House, you’ll hunt for specters and hear ghost stories.

Special Offer

Tourgoers in front of the Marshall Field Mansion

Prairie Avenue Haunted History Tour and Ghost Hunt

5.0

(12)

2 hours 20 minutes

from

$32

$37

Book your private transfer from Chicago O`Hare Airport (ORD) to Chicago and return. Avoid the hassle of waiting in long taxi or shared shuttle queues and use our private, door-to-door airport transfer. Your driver will be waiting for you at the scheduled time, and you can travel comfortably to your destination. • We track your flight. • Our driver greets you with a name plate. • We provide door-to-door service. • There are no hidden charges. • We use clean cars and professional drivers.

Chicago O`Hare Airport (ORD) to Chicago: Round-Trip Transfer

Free Cancellation
1 hour

from $202

Book with us for unmatched luxury and service: Premium Experience: Enjoy sophistication and style with our luxurious fleet and tailored experiences. Professionalism: Our skilled chauffeurs prioritize your comfort and safety, ensuring a seamless journey. Customization: Tailor your trip to your preferences, making every detail unforgettable. Convenience: Seamless booking, real-time tracking, and 24/7 support make travel effortless. Value: Experience luxury at competitive prices with transparent rates and unbeatable value. Safety: Your safety is our priority, with stringent measures and expertly trained chauffeurs. Choose A1 Chicago Limo Services for an unparalleled travel experience. Book now and elevate your journey.

Luxury Sedan 4 Hours Sightseeing Tour

Free Cancellation
2 to 4 hours

from $250

Experience Chicago from the water on a captivating history tour along the iconic Chicago River and Lake Michigan. As you glide through the heart of the city and the Chicago Harbor Lock, expert guides bring the past to life with stories of Chicago’s rise from a frontier town to a world-class metropolis. Discover legendary events like the Great Chicago Fire, marvel at historic landmarks, and gain a deeper appreciation for the maritime history that shaped the city you see today. Travel through the Chicago Harbor Lock and learn about the engineering marvels that reversed the flow of the Chicago River. Learn about how the Chicago Harbor Lock connects the Great Lakes to the Mississippi watershed.

Chicago River and Lake Michigan History Boat Tour

10249

Free Cancellation
1 hour 15 minutes

from $46

Comfortable Roundtrip Tour from your hotel in Chicago to Chicago Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.

Private Shopping Tour from Chicago to Chicago Premium Outlets

Free Cancellation
5 to 6 hours

from $292

Come see Chicago's hottest up-and-coming burlesque stars! Experience the next generation of spectacle at Rising Stars, an alluring burlesque and variety revue that honors the Windy City's storied legacy of live entertainment. This high-energy showcase brings together the city's most captivating emerging burlesque dancers and variety entertainment for a night full of fun, whimsy, humor, and seduction. Whether you're a long-time fan of burlesque or a curious newcomer, we invite you to come enjoy Stars & Garters' intimate venue, world-class cocktails, and unforgettable performance artists. Every Rising Stars show features a unique roster of talent, so there's reason to come back again and again. (Follow @starsandgarterstheater on instagram to see when your favorite performers are scheduled for a show.)

Special Offer

Rising Stars Burlesque Revue Tickets in Chicago

Free Cancellation
2 to 3 hours

from

$24

$30

GPS Audioguide app: From Loop to Millennium Park (Offline).

Chicago, a city with undeniable charm, awaits you for a walking exploration of its 25 must-see attractions. From the Riverwalk to Marina City to the famous Cloud Gate, this tour takes you through the history and architecture of Windy City. See iconic venues like the Chicago Theatre and Willis Tower, while learning fascinating stories about Al Capone and Prohibition. An enriching experience for architecture, history and gastronomy lovers, all in one day. - 7.2 km tour through points of interest in Chicago - Discover the historical and modern heritage of the city - Explore at your own pace with captivating audio stories - Ideal for travelers in a hurry or those on a quick visit to Chicago

Chicago Audio Guided Walking Tour 3h and 25 Audio Commentaries

Free Cancellation
3 hours

from $7

Don’t rely on strangers or selfies to capture your vacation memories—with this private photoshoot experience, you’ll walk away from your Chicago getaway with professional photos to commemorate your experience. For solo travelers, the 30-minute Bronze Package offers 20 edited, hi-res photos; the 60-minute Silver Package is ideal for couples, and offers 35 photos; and the 100-minute Gold Package is perfect for larger groups, and offers 60 photos.

Private Photo Session with a Local Photographer in Chicago

3.0

(1)

30 minutes

from $294

From the Gotham chaos in The Dark Knight to the explosive battles of Transformers, Chicago’s skyline has played a starring role in countless blockbusters. On today’s Chicago Film and Television Tour, you'll explore the city through the lens of movie magic. Begin at one of Chicago’s most iconic theaters, seen in The Blues Brothers and Transformers. Stroll through downtown streets flanked by skyscrapers featured in the Joker’s money truck chase scene in The Dark Knight. At Union Station, relive the dramatic staircase sequence from The Untouchables, where Kevin Costner’s character battles criminals as a baby carriage tumbles down. Visit the University of Chicago, whose Gothic architecture and academic prestige have made it a popular filming location. Along the way, admire Chicago’s rare mechanical lift bridges and architectural wonders that make the city a perfect backdrop for filmmakers. In Chicago, every corner holds a scene, and every street tells a story—waiting for you to explore.

Iconic Action Film and Movie Locations 1 Day Tour in Chicago

Free Cancellation
9 hours

from $151

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Amena_S, Apr 2026

Top tier experience

It was amazing from start to finish. Very aesthetically pleasing and service and food was top tier. Our server Heather was a perfect 10 across the board. Her recommendations, her spirit, her genuine energy was a breath of fresh air. She helped us with food selections, which were amazing down to photo opportunities. She even led us to the amazing bartender Keisha who made the best bottomless mimosas to say the least. We had to stop by the bar to let Ms Keisha know how well she mixed those cocktails. This was truly an amazing birthday brunch experience. Great way to start my birthday!!!

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Bysheera_H, Mar 2026

Loved it!

The line moves rather quickly. Be on time so you don’t have to rush. Our tour guide John was phenomenal, his knowledge of Chicago’s architecture was expansive and he made us laugh throughout. The views are gorgeous and the ride was smooth. We went at sunset and it was worth it! Lastly, dress warm.😄

Chicago Favorites Ultimate Food and Walking Tour

Jennifer_H, Mar 2026

I had an incredible time...

I had an incredible time on the Chicago Favorites Food & Walking tour, and a huge part of that was our guide, Gabe! He was the perfect mix of entertaining and informative. It’s rare to find someone who is so clearly an expert on the city but also has a great sense of humor that keeps the energy high the whole time. You can tell Gabe truly loves what he does, and it made the entire experience feel special. Highly recommend requesting him if you can!

Chicago River 90-Minute Architecture Tour

Katie_M, Mar 2026

Our tour guide John made the experience even more AMAZING!

John from Wendella was our tour guide and he was AMAZING!! My entire family was so entertained by him. He was HILARIOUS and 1000% made the tour so much fun! He has to be a comedian, he was so funny. We just loved him! And the architecture was breathtaking. I would definitely recommend taking this tour. And get John as your tour guide!

Chicago Architecture River Cruise

Janelle_B, Mar 2026

Take this tour

This is a great tour! It provides up close views of the Chicago skyline and riverfront. Our guide Richard shared many stories about Chicago history and facts about its architecture while keeping the conversation interesting with a touch of humor. I would highly recommend the tour for the boat ride, views of the skyline and riverfront alone, but you probably will also learn a few new facts about Chicago and its architecture as a bonus.

Chicago Architecture Center River Cruise aboard First Lady

Christina_T, Mar 2026

A must do while in Chicago

Booked this tour over the other operators because of the contributions the company gives back to non-profit organizations and the tour did not disappoint. Mark was our guide and he was extremely knowledgeable. The views of the skyline, Wrigley Tower, Sears Tower, etc. were breathtaking. Highly suggest for anyone interested in the architecture of Chicago or just wanting a nice night out with amazing views. Will definitely book again when in Chicago.

Field Museum of Natural History Admission Tickets

Julie_C, Mar 2026

Too Much for 1 Day

There is so much to see and explore. Get rest before coming and go see the things you’re interested in first. There is so much to see and experience that it can’t be done in a single day. My kids have very different tastes and we split up. There was something of intense interest for both.

Chicago Crime and Mob Bus Tour

Jean_P, Mar 2026

My birthday experience

This was our first bus tour in Chicago. The address was for a library, so we went inside. The library worker told us a bus would be out front, so we asked one of the bus drivers and he was the driver for our tour. It was a beautiful day, and also my birthday, and we enjoyed the tour very much. Jay, was the guide and she was very knowledgeable and offered many tidbits to the tour.

Flyover in Chicago

Krystal_M, Jan 2026

Flyover with friends

I had an incredible time! I feel like every city should have something like this! We got to experience the whole city without actually stepping foot in some of the cities most highlighted landmarks. Of course we would actually want to see but our short time here would not permit. This was the next best thing you could do. Definitely recommend 10/10

Chicago Architectural River Cruise

Linda_L, Oct 2025

Awesome Experience

This was more than just an informative or educational experience. This was a totally awesome experience. Our guide, Tyler was exceptional. He really new his stuff. So very knowledgeable. I appreciate everything, it was wonderful. The weather was a bit chilly, but it didn't take away from the wonderful cruise we had.

Lake Michigan Sunset Cruise in Chicago

Lauren_T, Oct 2025

Our tour guide, John, was...

Our tour guide, John, was full of energy and provided plenty of knowledge about Chicago history while making it a fun environment. The music was a variety of genres so there is something for everyone. We didn’t purchase any beverages while on the cruise, but they did let us know it was available. Worth the money for sure! Picture worthy.