Top Chicago City Tours - page 3

Chicago Private Night Skyline and Lakefront Scenic Tour

Price varies by group size

from $116

There’s so much amazing architecture in Chicago but wandering around alone can leave you overwhelmed, and unsure of what you’re looking at. Check out some of Chicago's most important new buildings on an architecture walking tour. The tour is focused on the area around the Chicago Architecture Center (CAC), beside the Chicago River, so you don’t get overwhelmed exploring the whole city. Admission to the CAC’s galleries is also included.

Chicago Architecture Walking Tour: What's New

(80)

1 hour 30 minutesFree Cancellation

from $35

Experience Chicago in a new way on this small-group Segway tour. Visit Chicago’s "front yard," and see more of the sights in less time. Glide along the fragrant floral paths of Grant Park to the famous Buckingham Fountain. Then, travel along the banks of Lake Michigan to the Museum Campus for top-notch views of the city’s iconic skyline. Guided Segway training and helmets are included, making this a beginner-friendly tour.

Chicago Landmarks & Museum Campus Small Group Segway Tour

(230)

On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. Follow a local guide along quiet streets, city parks, and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. As you go, glimpse offbeat attractions like the Playboy Mansion, Oprah’s penthouse, and the Victorian houses of Old Town.

from $70

Smiles ear to ear as you ride our Chicago Bike Tour through scenic Lakefront Neighborhoods. Fresh air, open paths, and lake views make this the ultimate Bicycle Tour in Chicago.

Bike Tour of Chicago's Lakefront Neighborhoods

(241)

3 hoursFree Cancellation

from $59

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables, The Dark Knight, The Bear, and more. See the theater from Public Enemies, Harold Washington Library from Ocean’s Eleven, the Chicago Board of Trade and Calder’s Flamingo from Ferris Bueller, iconic Blues Brothers spots, and Bruce Wayne’s penthouse and Harvey Dent’s office from The Dark Knight. Perfect for film buffs and Chicago enthusiasts alike.

Private Downtown Chicago TV and Movie Sites Guided Walking Tour

4.7

(3)

2 hours

from $132

Price varies by group size

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

3 hoursFree Cancellation

from $7

Embark on the adventure of a lifetime! Step aboard the iconic California-Chicago Train Expedition as we whisk you away on a journey that combines the thrill of train travel with the magic of California's breathtaking scenery. From the vibrant streets of Oakland to the sun-kissed Lakes of Salt Lake City, discover the majestic United States, like never before. Immerse yourself in the glitz and glamour of Las Vegas, experience the majesty of the Sierra Nevadas, and savor the world-class views of the Rocky Mountains. With luxurious accommodations, gourmet dining, and expertly guided excursions, this is the tour that dreams are made of. You can start from either CA, CO, or IL. Don't worry about other people, this tour is completely tailored to you with the Pintours App! With our app, you can pause the tour, and check out the locations as long as you want! You can skip a stop you don't like, and you have all the best information about each stop at your fingertips.

Continental US Train Zephyr Adventure CA -CO - Il

3.5

(2)

3 daysFree Cancellation

from $5

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)

Experience Chicago in unparalleled style with a 10-mile cruise through the city in a luxury or exotic vehicle. Glide through iconic streets, turning heads at every stop, while taking in the captivating sights of the Windy City. Whether you're a resident or visitor, this exclusive ride offers a fresh perspective of Chicago's vibrant energy and charm. Don’t miss the chance to explore the city like never before—reserve your adventure and drive through Chicago’s heart in true sophistication. All tour vehicles are subject to availability During This Ride You May See Views Of The Following Land Marks: Little Italy Willis Tower Harold Washington Library The Chicago Theatre Millennium Park Grant Park Buckingham Fountain Magnificent Mile Gold Coast Museum of Science & Industry Lake Michigan And much more! We cannot guarantee that all sites on this list will be seen in your tour.

from $70

Uncover Chicago’s Most Bespoke Shopping Destinations

Downtown Chicago City Tour In a Lamborghini[60 Minute Experience]

45 minutes to 1 hour

from $99

Likely to Sell Out

️ Chicago Instagram Walking Tour (Private & All- Inclusive)

(2)

4 hoursFree Cancellation

from $236

Discover many of Chicago's best-known landmarks—and explore without breaking a sweat—on this private electric bike tour. Meet your guide right at the Buckingham Fountain, grab your e-bike and helmet, and get ready to explore. You'll view Lakefront landmarks like the Field Museum and Adler Planetarium, will zip right along the waters of Lake Michigan, and will stop to soak up picture-perfect views of the Chicago skyline.

Chicago Lakefront Electric Bike Tour

4.5

(17)

45 minutes to 1 hourFree Cancellation

from $69

4.5

(16)

Chicago Helicopter 25-Mile Tour for up to Three Passengers

15 minutesFree Cancellation

from $650

Get a chance to experience the Windy City from multiple vantage points during this two-hour, small-group boat tour in Chicago. Hop aboard a secure and reliable US Navy-built Rigid Inflatable Boat (RIB) for a unique sightseeing experience. Pass by iconic sights such as Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and more, all while comfortably seated in a group capped at only six people.

Small-Group Sightseeing Boat Tour in Chicago

(95)

1 hour 30 minutesFree Cancellation

from $89

Get to know the foodie Chicago neighborhood made famous by "The Bear"—and taste your way through some of the Windy City's best bites—on this small-group walking tour of River North. Visit locals-loved hotspots that represent the best of the city's dining scene, and Be sure to come hungry: You'll try everything from tacos and Italian beef sandwiches to deep-dish pizza, all while learning about the neighborhood's history and food culture.

River North Food Walking Tour

4.7

(88)

3 hoursFree Cancellation

from $89

Step into the heart of Chicago with this in-depth, small-group walking tour of the Loop neighborhood, the heart of the Windy City's downtown. Stop to check out the elevated “L” train, admire historic buildings, discover lesser-known corners of this vibrant area, and view its best-known public artworks, too. You’ll come away with a deeper sense of Chicago’s rich history and architecture.

Chicago Loop Walking Tour

(55)

Sample some of the Windy City's tastiest donuts—and head to locals-loved dessert destinations that most visitors miss—on this one-of-a-kind walking tour. With your guide in the lead, head to a number of Chicago’s tastiest donut bakeries, all while exploring the city's vibrant downtown Loop neighborhood. All tastings are included in the tour cost, and vegan, gluten-, and nut-free options are also available upon request.

from $60

Delicious Donuts & City Sights: Chicago's Original Donut Tour

(1,409)

Delve into the rich history and notable architecture of one of Chicago’s most luxurious neighborhoods—and learn insider stories as you go—with this self-led smartphone audio walking tour. Upon booking, download the app and set off at a time and pace that work best for you. You’ll discover Gold Coast landmarks from historic piano bars to the original Playboy Mansion, and can stop and start the tour whenever you like.

from $70

Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk

4.3

(7)

50 minutes

from $8

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 10 PASSENGERS TOTAL. Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago. Our services include pick up from your downtown Chicago hotel, a 3-4 hour private City Tour in a chauffeured vehicle, and the services of one of our knowledgeable guides. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops. These stops include, but are not limited to Millennium Park, Lincoln Park Conservatory, Museum Campus, and more. The tour will be interactive and entertaining, covering history, architecture and culture. We share stories to bring Chicago's rich history to life. Once the tour concludes, we will drop your group off at your preferred, downtown Chicago location.

Private City Tour 6-10ppl

(2)

3 to 4 hoursFree Cancellation

from $770

Taste food from around the world—and immerse yourself in some of the Windy City's most characterful, locally beloved neighborhoods—on this half-day biking and tasting tour of Chicago. With just a small group for company, you'll follow your guide through the city streets, stopping for views of Chicago’s famous architecture and seeing more than you could if traveling on foot. In between, stop for bites like Polish pierogis, locally made chocolates, and Mexican tacos.

Taste robust flavors on our Chicago Food & Bike Tour. Ride a Bicycle through the Westside and savor bold bites—one of the top Culinary Things to do in Chicago.

Chicago's West Side Foodie Ride Bike Tour

(112)

4 hoursFree Cancellation

from $99

Private Wicker Park and Bucktown Walking Tour

(3)

2 hours 30 minutesFree Cancellation

from $195

Chicago is world-renowned for its architecture—and this small-group walking tour offers the ideal introduction to its iconic buildings, its architectural eras, and the starchitects who have left their impression on the city. Meet your guide at the Chicago Architecture Center and set off on foot: you’ll discover highlights like the Wrigley Building and Marina City, will see works by Renzo Piano and Frank Gehry, and will learn all about Chicago history.

Chicago Walking Tour: Connecting Past and Present

(38)

1 hour 45 minutesFree Cancellation

from $35

4.3

(6)

Private Frida and Friends Tour in Pilsen

from $240

Lakefront Segway Tour in Chicago

4.6

(145)

1 hour 30 minutesFree Cancellation

from $75

Chicago Architecture Tour - Skyscrapers, History and Photo Ops

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and construction history. Get a unique chance to combine touring by foot and by L train, and see the city’s most iconic landmarks like The Rookery Building, Chicago Cultural Center, First Arts Building, and more 19th and early 20th-century masterpieces. Be ready to see the City by the Lake from a new perspective and get to know it even closer as you stroll down its streets and travel by train. Enjoy the small-group experience and don’t miss a thing as you travel Discover the downtown and historical building together with your local knowledgeable guide Marvel at architectural landmarks of the City by the Lake and get to know the stories behind them Combine a walking tour with a train to see more landmarks and iconic sights on one tour.

2 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops

(1)

Chicago River 90-Minute Architecture Tour

from $89

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Top Attractions in Chicago

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What are people saying about Chicago

CHELELL_G, Apr 2026

The best architectural boat cruise in chicago.

The architecture tour was amazing the tour guide was very knowledgeable about the towers when they were built and the history about it .the views are spectacular I highly recommend any one that has the love for architect and skylines to take this tour.

Chicago Architecture River Cruise

Katy_A, Apr 2026

Excellent boat tour

The boat architecture tour did not disappoint! The guide was excellent. He kept things entertaining and informative. The length of about an hour and fifteen minutes was perfect. I had to make a last minute time change and they cheerfully accommodated my request. Highly recommend!

Chicago in a Day: Food, History & Architecture Walking Tour

Tracey_M, Apr 2026

Brilliant tour of Chicago

A lot of walking but the pace is decent and is totally flat. Some stairs but that’s inside the buildings Dash was my guide, knew loads about the city and made the tour truly interesting! I learnt so much from it and was made extra special as I’d done the boat tour the previous day and had seen the exterior of the buildings but Dash took us inside to view the architecture and extended his knowledge of which was really informative. We rode the train loop and was able to see inside the floors and other architectural features on the sides of the buildings We sampled chocolate brownie, Chicago's hot dog, beef sandwich and deep dish pizza A fantastic tour, so pleased I booked it early on my trip (day 2) as it helped me get my bearings of the city Thanks Dash, truly thankyou for a fab tour !!

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Louann_M, Apr 2026

super enjoyable and informative architectural rivercruisr

I followed my maps but when I arrived the boat entrance wasn't marked well, but otherwise the whole experience was great! it was very easy boarding and getting a seat, the staff were all so nice…the tour was just long enough and the gal tour guide was lovely with an english accent, nice to listen to. We learned a lot about Chicago’s history along with timeline of the buildings how they were built and special building materials used, super interesting and well done. it was a lovely day as well which made it so nice, I highly recommend, is my first time to Chicago, great thing to do for all ages!

Chicago Favorites Ultimate Food and Walking Tour

Marsha_M, Apr 2026

5 STARS ASK FOR MICKY. Great entertainment

This food tour is more than just eating! Micky is a top notch guide and you learn the history and legends about Chicago. All the Food was fantastic! There are just enough places that you don't get too much. The nice walk around after each stop was timed well. The entire tour was entertaining. Ask for Micky as your guide.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Cristina_M, Mar 2026

Great tour to learn about Chicago in less than 2h!

The tour was great! We were in Chicago less than 2 days as my colleague and I were coming back from work meetings in other state and we didn't have a lot of time to explore the city on our own. We learn a lot from Spencer (our guide) not only about interiors but also about the history and culture of the city. He also pointed out scenes from famous movies which make it fun! He made us very cool photos and Also he recommended us a few places to have a proper Chicago lunch 😋 and also send us after other recommendations to do. Really enjoyed our time in the city and obviously the tour! Thank you Spencer! 😉

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 Night Crimes Tour by Bus

Crystal_M, Oct 2025

Had an amazing time on...

Had an amazing time on this tour!!!! Hearing the stories and stoping at some of the same locations these gangsters and outlaws actually visited , stood, worked and even lost their lives at was quite the experience! The bus driver and tour guide were very professional . Our transportation bus was very nice, clean and comfortable. So glad I took this tour!! Thank you !!!