Top Chicago City Tours - page 4

BYOB Chicago River Guided History Tour

Chicago River Tiki Bar Party Cruise from Chicago Riverwalk

(4)

from $65

1 hour 15 minutes

4.0

(123)

from $42

Chicago Architecture Walking Tour: What's New

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

1 hour 30 minutesFree Cancellation

Get to know the “must eats” in Chicago's buzzing Loop District on this small-group or private walking tour. As you explore, listen to in-depth commentary from your guide about the culinary history of Chicago, and get a taste of the city's most iconic foods, from hot dogs to deep-dish pizza. You'll enjoy personalized attention and the chance to chat about your favorite tastings, all while admiring Chicago landmarks along the way.

(90)

from $35

Chicago Loop Food Tour: Taste the Most Iconic Local Eats

4.8

(122)

from $87

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

Chicago Walking Tour: Connecting Past and Present

1 hour 45 minutesFree Cancellation

Experience the best of the Chicagoland area in style and comfort with our exclusive SUV tours. Discover the city's iconic landmarks, including the breathtaking parks, the famous Cloud Gate (The Bean), world-class museums, and renowned stadiums. Whether you’re attending a concert, exploring historic sites, or enjoying a day at the park, our professional chauffeur service ensures a seamless and luxurious journey. With our SUV tours, you'll have the flexibility to explore at your own pace. Visit top attractions like Millennium Park, the Art Institute of Chicago, and the Field Museum. Enjoy a thrilling game at Wrigley Field or United Center or take in a concert at Allstate Arena. Our chauffeur will drop you off and pick you up at each location, providing you with the utmost convenience. Book your tour today and let us take care of the details. Travel in comfort and make the most of your time in Chicagoland with our premium SUV tour service.

(43)

from $35

Luxury SUV 4 Hour Sightseeing Tour

from $350

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

Experience the best of America’s Great Lakes region on this five-day guided road trip from Chicago. Travel along scenic routes to iconic lakeshores, enjoy in-depth tours of Pictured Rocks National Lakeshore, and discover cultural landmarks in Chicago, Milwaukee, Traverse City, Mackinac Island, and Holland. Your itinerary balances history, nature, and local flavor, with comfortable vehicle transport, professional guides, and daily breakfast included. Designed for travelers who want to see more than city highlights, this journey offers a true taste of Midwestern adventure—with plenty of opportunities for sightseeing, local cuisine, and unique attractions along the way.

4.9

(56)

from $60

5-Day Tour of Superior, Huron and Michigan from Chicago

5-Day Tour of Superior, Huron and Michigan from Chicago

5 daysFree Cancellation

from $1,348

It would take days to visit all of Chicago’s famous sights, but who has that kind of time? Cover the highlights of the Windy City during this private half-day walking tour. From the Magnificent Mile to Millennium Park, you’ll tick off top attractions while your guide fills you in on Chicago’s history. Finally, enjoy panoramic views overlooking the city from Hancock Tower’s Observation Deck—admission tickets included.

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

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

3 hoursFree Cancellation

(3)

from $240

Haunted Ghosts & The Chicago Outfit Segway Tour

Likely to Sell Out

️ Chicago Instagram Walking Tour (Private & All- Inclusive)

4.7

(38)

from $75

Likely to Sell Out

4 hoursFree Cancellation

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!

from $236

Chicago Small Group City Tour

9 to 10 hoursFree Cancellation

from $465

Enjoy an immersive way to discover Chicago's more recent architectural heritage with this small-group walking tour. Led by your architectural expert guide, you'll discover many of the Windy City's modern, postmodern, and other newer structures, including works by architects like Mies van der Rohe, Bertrand Goldberg, and beyond. As you go, your guide will point out the buildings many visitors overlook, and share stories from their history you wouldn't otherwise hear.

Chicago Walking Tour: Modern Architecture

1 hour 30 minutesFree Cancellation

4.9

(67)

from $35

Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

Explore the best of the Great Lakes region on this four-day tour departing from Chicago. Travel through lakeside cities like Milwaukee, Green Bay, and Traverse City, discover national parks and stunning beaches, and visit the iconic Mackinac Island—ranked among the world’s most beautiful islands. Guided by local experts, you’ll enjoy scenic walks, museum visits, and the region’s natural wonders with comfortable transport and included breakfasts. This well-paced trip gives nature lovers and explorers the ultimate lakeshore adventure across Superior, Huron, and Michigan.

Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

4 daysFree Cancellation

from $1,125

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

3 to 4 hoursFree Cancellation

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 works best for you. Discover Gold Coast landmarks from historic piano bars to the original Playboy Mansion, and stop and start the tour whenever you like.

from $770

Per group

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

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

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

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.

from $89

Continental US Train Zephyr Adventure CA -CO - Il

Continental US Train Zephyr Adventure CA -CO - Il

3 daysFree Cancellation

3.5

If it’s your first time in Chicago or you just have limited time, make the most of a day in the Windy City on a private driving tour. Instead of navigating public transit or waiting for ride shares, relax as a dedicated driver takes you to all the major attractions of downtown and beyond, including Navy Pier, Michigan Avenue, Wrigley Field, Millennium Park, and Museum Campus. Plus, get local insight into Chicago along the way.

from $5

Luxury Sedan- Lincoln Continental, Cadillac XTS, Lincoln MKT or similar

Chicago 6-Hour City Tour by Sedan

6 hoursFree Cancellation

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.

from $960

Per group

Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour

Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour

2 hours

4.7

(3)

from $132

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the footsteps of the gangsters, bootleggers, hoodlums, gunmen, and crooked cops and politicians who made up what was known as the “Chicago Outfit” • Hear from producer Richard Junger, an urban historian, professor and author passionate about Chicago • Do it all in 45 minutes or linger at stops along the way with complete control over when you start and finish • Get unlimited use before your booking date and after it • Use the virtual tour option at home Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the VoiceMap app and enter your code. The app displays directions to the starting point, and when you’re in the right place, just pop in your headphones and tap start. VoiceMap has automatic GPS playback, with turn-by-turn directions. It also works offline.

Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

45 minutes to 1 hour

3.0

from $7

Skyline, Lakefront and Millennium Park Chicago Private Day Tour

Explore Chicago’s iconic landmarks and scenic lakefront on a private, fully personalized city tour. Travel in comfort with your English-speaking driver, who shares local stories, history, and insights while guiding you through the city’s most famous sites. Begin at Millennium Park to see the iconic Cloud Gate sculpture (“The Bean”), then visit Buckingham Fountain in Grant Park for stunning lake and skyline views. Drive through downtown to admire the Willis Tower Skydeck area, then enjoy the Chicago Riverwalk and Wacker Drive for striking architectural vistas. Continue to Navy Pier with its attractions and Centennial Wheel, then take a scenic drive along Lake Shore Drive for panoramic lakefront skyline views. Conclude at Lincoln Park and North Avenue Beach for one of the city’s most memorable photo spots. This flexible, door-to-door private tour offers a relaxed and immersive way to experience Chicago’s architecture, waterfront, and vibrant urban culture.

Skyline, Lakefront and Millennium Park Chicago Private Day Tour

3 hoursFree Cancellation

from $167

Take to the skies and experience Chicago from an entirely new perspective on this extended helicopter tour showcasing the city’s most iconic landmarks, neighborhoods, and waterfront views. The flight begins near the Chicago Fire Practice Facility before heading over Chinatown, where colorful architecture and historic streets create a striking aerial view. From there, you’ll pass McCormick Place, the largest convention center in North America, stretching along the lakefront and highlighting the scale of Chicago’s downtown footprint. Continuing north, you’ll fly over Northerly Island and Soldier Field, followed by the heart of the Museum Campus, where the Field Museum and Adler Planetarium sit against the backdrop of Lake Michigan. Grant Park comes into view next, often called Chicago’s front yard, leading to an aerial look at Millennium Park and the unmistakable curves of The Bean.

Chicago Helicopter Tour: Loop Tour

12 to 15 minutesFree Cancellation

3.0

Your journey begins with a southeast departure from the Vertiport, offering early views of the city’s iconic skyline. Flying east, you’ll head toward the lakefront and cruise south along the shoreline, passing Soldier Field, the Museum Campus, and continuing down to the historic Museum of Science and Industry in Hyde Park. From there, the route turns north, following Lake Michigan’s edge past Navy Pier, the John Hancock Center, and up to Montrose Harbor; a favorite city escape with marinas and beaches. You’ll then loop south once more, enjoying a sweeping view of Chicago’s lakefront before heading west to return to the Vertiport. It’s a dynamic tour showcasing both downtown and the scenic south shore in one unforgettable flight.

from $210

Chicago Helicopter Tour: City to Shoreline

Chicago Helicopter Tour: City to Shoreline

20 to 25 minutesFree Cancellation

4.2

(9)

from $350

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Chicago City Minibus Tour

Patti_B, Jul 2026

Our tour guide Alan was...

Our tour guide Alan was wonderful l! We had a great overview of the the city without being rushed. Alan also recommended a place for pizza after the tour and dropped us off at the restaurant so we didn't need to walk. Would highly recommend this tour and hopefully you'll be lucky to have Alan as your guide.

Chicago Architecture River Cruise

Kyuin_S, Jul 2026

Architecture tour

I took the 9:15 PM architecture tour and it was such a fun way to be a tourist in Chicago! The tour guide (who also hosts a podcast!) was amazing, super knowledgeable, explained everything so well, and made the whole experience really fun. I already recommended this tour to my friends, and they booked it for tonight! This tour seriously made me want to move to Chicago

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

Arianne_T, Jul 2026

Great tour hitting...

Great tour hitting architecture inside and outside with food experiences unique to Chicago! Our tour guide, Dave, was both friendly and knowledgeable and even brought cold water bottles for the entire group since it was hot outside during our tour! Would highly recommend for anyone who is looking to get their steps in while hitting the main attraction sites!

Chicago River 90-Minute Architecture Tour

Ryan_W, Jul 2026

Trip was very interesting...

Trip was very interesting and informative. The narrator was excellent! He had a great presentation and delivery, was very entertaining, and had a clear passion for the topic. I would highly recommend this to everyone from kids to seniors (which the the age range of our group)

Chicago Architecture Center River Cruise aboard First Lady

Beth_W, Jul 2026

Will definitely be back….Again!

The Architectural River Tour never disappoints! The Chicago skyline is constantly evolving, so every trip down the river feels fresh and exciting. There’s always something new to learn or notice, and the guides make the experience even better. Matt was fantastic—knowledgeable, engaging, and clearly passionate about the city’s history and architecture.

Chicago Lake and River Architecture Tour

Ioana_C, Jul 2026

Best tour of Chicago river and lake.

Best combination of lake and river tours. The Chicago skyline is wonderful to see it in its entire length and beauty from Lake Michigan. The tour guide was very knowledgeable and had a wonderful story to tell at “every corner”. Toilets were clean and there was no problem finding where to sit. We did not buy anything from the bar but everything looked clean and nice. Total duration of the tour is one and a half hours spent approximately half-half between the lake and the river part. Fun fact: lake is a couple of feet higher than the river and you can see that when crossing over during the tour. Chicago river flow direction was altered in the early 1900 to flow away from the lake and keep chicagos source of clean water intact.