All Chicago Tours &amp; Excursions in 2026 - page 5

Verse Immersive Holographic Theater in Chicago

from $52

4.2

(34)

30 minutesFree Cancellation

from $40

4.8

(41)

O'Hare Airport Transfer to Chicago, Sedan, Curbside - Top Rated

30 minutes to 1 hourFree Cancellation

from $133

Chicago Walking Tour: Must-See Chicago

(141)

1 hour 30 minutesFree Cancellation

from $35

Explore Chicago by Segway with the benefit of a scenic 7- or 8-mile tour led by your guide. Start with an orientation to operating the Segway and a few minutes to practice. Then roll through the paths of Grant Park to Buckingham Fountain and glide along the Chicago lakefront to view attractions such as Museum Campus, Shedd Aquarium, The Field Museum, and Soldier Field, homefield for the Chicago Bears.

2-Hour Chicago Lakefront & Museum Campus Segway Tour

(348)

Enjoy an active and entertaining way to explore Chicago’s highlights with this small-group Segway tour. Meet your guide at a convenient location in downtown Chicago, get acquainted with your Segway before setting off, and then hit the road. You’ll discover top Windy City highlights, including Millennium Park, the Buckingham Fountain, the Museum Campus, and more, all while learning about the city’s history and insider facts from your guide.

from $70

2-Hour Guided Segway Tour of Chicago

4.7

(493)

from $65

Lincoln Park Hauntings Ghost Investigation Tour

(45)

2 hours 15 minutesFree Cancellation

from $40

- Chicago's Highest Rated Limo And Car Service - 10 Years in the limousine business - Proven track of exceptional customer service - Professional, Safe, Fully Uniformed Chauffeurs - FBI Background checks for all drivers - $350,000 Commercially Insured - GPS tracking devices on all vehicles - "Driver ON Location" automated text message - Chicago Based company Skip the stress of a taxi or shared shuttle between Chicago downtown and O'Hare airport with the Highest rated limousine service in Chicago on Trip Advisor and Yelp. A professional driver will pick you up at Chicago O'Hare Airport at curbside. Travel in a comfortable, newer private sedan for a safe and relaxed ride. All our drivers are licensed and insured and all our sedans carry a $350,000 insurance policy.

O'Hare Airport Transfer to Chicago by Luxury Sedan - Inside Meet

(6)

30 minutes to 1 hourFree Cancellation

from $154

A piece of cheese showing what I look for to tell your fortune.

Fortune Reading with Cheese in Chicago

(23)

Discover some of the Windy City’s spookiest ghost stories—and step back in time to the era of gangsters, bootleggers, jazz performers, and more—on this small-group walking tour. Meet your guide in Chicago’s Lincoln Park neighborhood, and set off after dark. You’ll visit supposedly haunted former burial grounds, pubs, theaters, and more—and will hear about macabre legends and unexplained happenings as you go.

from $65

Feel the presence of the unseen as we wander through haunted history under the moon's glow.

Embers of the Windy City: Chilling Chicago Ghost Tours

4.4

(121)

Skip the guesswork and discover the real haunts of Capone, Dillinger, and The Outfit on a walking tour that then also you shows how those same streets become movie stars. Walk the city corners seen in *The Untouchables* and *Public Enemies,* and hear how Chicago wrote the script for American gangster history. This isn’t just another sightseeing tour—it’s a front-row seat to crime, cinema, and the city that made them both.

from $26

Chicago Crime and Movies Tour

(52)

1 hour 30 minutesFree Cancellation

from $35

Discover one of downtown Chicago's highlight museums, and explore the works of leading artists across myriad media and genres, when you book tickets to the Museum of Contemporary Art. Choose from multiple entry times throughout the day, make your own way to the museum, and get ready to explore. Exhibitions are ever-changing, but you can expect to see works by artists the likes of Kara Walker, Jasper Johns, Cindy Sherman, and beyond.

Chicago Museum of Contemporary Art: General Admission Ticket

3.5

(92)

1 to 3 hoursFree Cancellation

from $22

Sit back and take in some magic—and enjoy a one-of-a-kind night on the town—during this engaging Chicago show. Show up a few minutes before curtain time to get the best possible seat and start sipping the drinks you brought. Cups and bottle openers are available for your use. Buying your tickets in advance means less waiting for entry; you'll be sure to get the day and time you that fits your schedule.

Trickery Chicago Magic Show

(96)

1 to 2 hours

from $41

Glide through Millennium Park’s ice rink on your Chicago Seasonal Tour, where bright lights and winter fun capture the Chicago Holidays and Christmas spirit.

Discover many of Chicago’s best-known landmarks—and see the city dressed up in its festive best—on this holiday walking tour of the Windy City. Come bundled and join your guide and small group to explore the famous Christkindlmarket. Then continue to discover Millennium Park’s ice rink and Christmas tree, stroll the Magnificent Mile’s glowing lights, and more while you hear fun facts and cultural insights from your guide.

Chicago Seasonal Stroll Walking Tour of Holiday Attractions

(5)

Travel through architectural history on this express, small-group walking tour, which covers Chicago's most famous buildings in chronological order (and which is speedy enough to cater to the most time-pressed travelers). With a guide in the lead, there's no need to fuss over maps or worry about directions. Simply stroll along and listen to the in-depth commentary on Chicago's architectural history; you'll learn about each building, and will have plenty of chances to stop for photos.

from $45

Chicago Walking Tour: A Walk Through Time

(207)

1 hour 30 minutesFree Cancellation

from $35

Embark on a captivating walking tour that delves into the intriguing legacy of the Midwest's most notorious mobsters and gangs. Immerse yourself in the rich history of the Windy City as you stroll through its vibrant streets, where the echoes of a century of Mob activity intertwine with the modern cityscape. Traverse the iconic Michigan Avenue, once a hub of illicit operations masterminded by the infamous Al Capone, and uncover the hidden secrets of the past that now lie beneath the surface of changing demographics and contemporary establishments. Brace yourself for chilling tales of mob hits and ongoing underworld dealings, as you unravel a dark and compelling narrative that still resonates through the streets today.

Gangs and Mobsters Crime Tour at Chicago

(2)

Set sail for a memorable experience on Lake Michigan with a Signature Chicago Brunch Cruise that is as scenic as it is delicious! You'll savor a chef-prepared buffet and bottomless mimosas while in our comfortable indoor areas. Marvel at unparalleled views of Chicago’s iconic landmarks, such as Willis Tower and Navy Pier from inside or enjoy fresh breezes on the open-air decks. This fun-filled brunch cruise experience for all ages is complete with lively DJ entertainment, dancing, games, and a fully stocked cash bar. Elevate your weekend plans with a one-of-a-kind brunch cruise on the water!

from $26

City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

4.3

(3)

Discover one of Chicago’s top architectural marvels when you explore Frank Lloyd Wright’s UNESCO-listed Frederick C. Robie House, located right on the University of Chicago’s campus. Considered a masterpiece of Prairie School architecture, the building is famed for its cantilevered roof and rich wood details. Save money when you book tickets to the house in advance; call ahead to reserve a space on one of the museum’s frequent, small-group public tours.

from $94

Frank Lloyd Wright Robie House Admission

4.2

(132)

Best Chinatown Food and Walking Tour in town! The Chicago’s Chinatown Food and Walking Tour is a 3-hour immersive culinary and cultural experience designed to highlight the unique tastes, rich history, and vibrant culture of Chicago’s Chinatown. This comprehensive tour combines a curated food-tasting journey with an exploration of iconic landmarks, making it the most enriching and flavorful Chinatown experience available in such a short duration. All of the restaurants and shops we pick for you are our member businesses of Chicago Chinatown Chamber of Commerce with guaranteed food quality and hospitality! You get the most of your money and time! A minimum of 4 participants is required for this experience. If the minimum is not met, the tour may be canceled, and you will receive a full refund.

from $27

Taste of Chicago's Chinatown Food Tours

(2)

3 hoursFree Cancellation

from $85

Special Offer

Discover the unique flavor of our Absolutely Chicago E-Bike Tour. Experience the city's rich history, stunning architecture, and breathtaking views as you pedal along on our state-of-the-art electric bikes. From iconic landmarks to hidden gems, this unforgettable adventure combines adventure, warmth, and loads of fun. Immerse yourself in the vibrant atmosphere of Milton Olive Park, the wonder of Soldier Field, and capture unforgettable photos at the majestic Buckingham Fountain. With flexible routes and a focus on hidden treasures, our tour offers a truly unique and memorable experience through the heart of Chicago.

2 Hour Chicago Landmarks & Lakefront E-Bike Tour

(4)

Live the mythical Route 66 as it should be: at your own pace, with freedom and with the feeling of being walking a living history. This audio guide accompanies you from Chicago to Los Angeles, transforming each stretch of road into an experience full of context, curiosities and stories that give meaning to the journey. You don’t just drive – you understand the landscapes, cities and small towns that marked the American dream. No schedules, no groups and no rush, just you, the road and a voice that guides you at the right time. If you’ve always dreamed of doing Route 66 for real, this audio guide is the most authentic and simple way to live it.

from

$61

$72

Guided Audio Road Trip Route 66

6 daysFree Cancellation

from $30

Worried about navigating public transportation, or finding your own way to your hotel upon arriving in Chicago? Leave all the logistics to your driver instead—and enjoy a stress-free experience—when you book a private transfer service from either O’Hare or Midway International Airports. Meet your driver after grabbing your bags, hop aboard your air-conditioned vehicle, and relax as you’re whisked straight to your destination.

Private Transfer Chicago Airport MDW to Chicago Downtown

3.5

(54)

30 minutes to 1 hourFree Cancellation

from $50

Price varies by group size

Arrange for a stress-free ride to O'Hare International Airport (ORD) or Midway Airport (MDW) with this private transfer service. Meet your professional chauffeur at your hotel in downtown Chicago (or other Chicagoland destinations), and relax on the journey to the airport in a private sedan or minivan. You can leave the navigation to someone else, and reach the airport relaxed and in time for your flight.

Private Departure Transfer to Chicago Airports (ORD)(MDW)

3.8

(91)

from $90

Chicago River 90-Minute Architecture Tour

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Michael_B, Apr 2026

Great day out

Great experience,speaker was very informative!! I would definitely recommend this to anyone especially being from Chicago I felt ashamed not knowing a lot of the history. My city is very beautiful and has a great story behind it and the tour showed you it all.

Chicago Architecture River Cruise

Stacey_W, Apr 2026

Worth every penny!

Love this cruise! I would do it EVERY time I visit Chicago if I had the opportunity. Always learn something new. Our guide was very knowledgable. I love seeing the reflections of the mirrored buildings on each other. Such a beautiful skyline. It was a bit chilly October 31, but wear a winter coat, hat and gloves and you're good to go!

Flyover in Chicago

Sharon_S, Apr 2026

Great Experience...Flyover Chicago!

This was a great experience. You really feel that you are flying over Chicago. The ride is not "scary" as my daughter thought it would be (I think she was imagining a rollercoaster of some sort). You will get to see all of the highlights of Chicago and more...not spoiling it for you...go check it out!

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 Architecture Center River Cruise aboard First Lady

Elizabeth_T, Mar 2026

Anthony is the best!

This tour is an absolute must for anyone visiting Chicago. The First Lady is a beautiful boat and all the staff was very professional. Our guide Anthony was incredibly knowledgeable about the architecture and history of every building along the river as well as a lot of history regarding Chicago. His presentation was spectacular!! We will be back and highly recommend to others!

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 Architectural River Cruise

Christopher_M, Mar 2026

Excellent Chicago River Boat Tour

This was the best boat tour we have ever taken. Tyler was excellent. He was informative and very knowledgeable. He gave us an excellent overview of Chicago history and architecture. We appreciated that he did not try to be a comedian, as some guides do. The whole experience was enjoyable and informative. It was well worth the money and time. The rest of the crew was helpful and professional.

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.

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.