Top Chicago City Tours - page 3

River North Food Walking Tour

3 hoursFree Cancellation

4.6

(94)

from $89

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 $168

Take your architecture spotting off the streets and inside some of the most iconic buildings in Chicago with this unique Art Deco-themed tour. Get up close and personal with the glamorous style of the early 20th century as you delve beyond the downtown facades to explore glorious interior spaces from the 1920s and 1930s, with their ornate brass and marble details, mosaics, stained glass, and other treasures that most architecture tours miss.

Likely to Sell Out

Chicago Architecture Walking Tour: Incredible Art Deco Interiors

Chicago Architecture Walking Tour: Incredible Art Deco Interiors

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.

4.9

(114)

from $35

Chicago Walking Tour: A Walk Through Time

Lakefront Segway Tour in Chicago

4.9

(220)

from $35

Special Offer

Chicago Scenic Driving Tour

Chicago Night Crimes Tour by Bus

(22)

from $315

Per group

Stop off the bus at Chicago Landmark Building with Prohibition Era History

2 hours to 2 hours 30 minutesFree Cancellation

Enjoy an introduction to Chicago’s highlights and history—on wheels. This small-group Segway tour offers a new, and zippy, way to explore. Meet your guide near Millennium Park, and begin with a personalized training session. Once you’re comfortable on your Segway, explore Millennium Park, roll along the Lakefront, and more. As you go, learn little-known Chicago stories and tidbits, from mafia history to the innovations that changed the city.

(503)

from $55

Chicago Insider Segway Tour

Experience Chicago’s glowing skyline and scenic lakefront on a private, fully personalized night tour. Travel in comfort with your English-speaking driver, who shares stories and insights about the city’s architecture, neighborhoods, and history as the skyline comes alive after sunset. Begin along the Magnificent Mile, where illuminated skyscrapers and elegant streets create a stunning urban scene. Continue to the Chicago River for reflections of iconic buildings, then visit Navy Pier with its sparkling Ferris wheel and waterfront views. Drive along Lake Shore Drive to admire the dramatic skyline over Lake Michigan, and finish at Adler Planetarium for one of the city’s most spectacular panoramic night views. This flexible, door-to-door private tour offers a relaxed, immersive way to enjoy Chicago’s landmarks and lakefront illuminated under the night sky.

4.9

(52)

from $72

Chicago Private Night Skyline and Lakefront Scenic Tour

Chicago Private Night Skyline and Lakefront Scenic Tour

(1)

from $113

Chicago’s “L,” or elevated train, is an icon of public transportation and a major feature of the Loop neighborhood. On this interactive tour, you’ll learn about the railway’s history while experiencing it as a rider. Meet your guide in the morning and set off with just a small group for company. As you ride between stops, you’ll also view Chicago icons like the Willis Tower, and will learn about the city’s architectural history.

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Enjoy a fun and scenic 90-minute Cycleboat Cruise along the beautiful Chicago River! Take in stunning skyline views as you pedal, relax, and sip your favorite drinks with friends, family, or that special someone. • 1.5-hour cruise up and down the iconic Chicago River • Comfortable boat with 10 cycle stations and bench seating at the front • Maximum capacity of 16 passengers — perfect for smaller groups or couples • BYOB! Bring your own beverages and snacks to enjoy onboard • Departs from the Water Plaza on the Chicago Riverwalk (between Wells Street and LaSalle Street bridges) Whether you want a lively group outing or a relaxing ride through the city, this Cycleboat Cruise is one of the most unique ways to see Chicago from the water — no full-boat rental required!

(99)

from $35

Likely to Sell Out

Chicago River Cycleboat Cruise

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.

(11)

from $65

Chicago Lakefront Electric Bike Tour

45 minutes to 1 hourFree Cancellation

4.6

(18)

from $69

Have only a limited amount of time to explore the Windy City? Leave the planning to someone else with this convenient SUV transfer service. Meet your private driver at a time and place that work best for you, and set off: You’ll be dropped off directly at top Chicago landmarks like Navy Pier, Wrigley Field, Michigan Avenue, and Millennium Park, with time for solo sightseeing at each stop.

4-Hour Chicago City Tour by SUV

4 hoursFree Cancellation

Enjoy a new perspective on the Windy City—and see more of its sights in less time, all without breaking a sweat—on this small-group, sunset Segway tour. With included instruction and hands-on guidance, get comfortable on your Segway in no time. Then, set off to discover top Chicago highlights from the Museum Campus and Millennium Park to Buckingham Fountain and beyond, all while the city's lights slowly come on.

(2)

from $800

Per group

Special Offer

Chicago Sunset Segway Tour

Head to one of Chicago’s top neighborhoods for food lovers—and try donuts from four of the Windy City’s top specialty bakeries—on this indulgent walking tour. Meet your guide at the Chicago French Market in the morning, and come hungry: you’ll enjoy four different donuts, each representing different culinary styles and traditions. As you go, wander the West Loop and Restaurant Row, and learn more about Chicago’s dining scene.

Delicious Donuts & Sweet Treats: West Loop Walking Tour

1 hour 30 minutes to 2 hoursFree Cancellation

The Serial Killer & Iconic Chicago Landmarks Bus Tour

(75)

from $70

1 hour 30 minutes

Chicago Explorer Pass: 35+ Things To Do - Includes 360 CHICAGO

(1)

from $42

1 to 30 days

4.0

(362)

from $84

Chicago Walking Tour: Art Deco Skyscrapers Loop

Admire the ornamental facades and intricate interiors of the Windy City's art deco buildings during this in-depth walking tour of the vibrant Loop. This small-group tour will introduce you to some of the city's highlight architectural landmarks and its rich history, all in a single excursion. As you go, get an up-close look at landmarks that many other tours overlook—and learn insider stories from your architecture-expert guide.

Chicago Walking Tour: Art Deco Skyscrapers Loop

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.

(186)

from $35

Chicago Loop Food Tour: Taste the Most Iconic Local Eats

(122)

from $87

Chicago River Tiki Bar Party Cruise from Chicago Riverwalk

Likely to Sell Out

1 hour 15 minutes

4.0

(123)

from $42

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

See the best of the Windy City, all in just half a day—and learn the stories behind its best-known sights—on this private tour. In the morning, meet your driver at your Downtown hotel, hop aboard your private vehicle, and set off with a tour guide in tow. You can look forward to seeing sights like Grant Park, Navy Pier, and Buckingham Fountain—and stopping for photo opportunities along the way.

(5)

from $45

Private Chicago Guided Tour with Hotel Pickup

Private Chicago Guided Tour with Hotel Pickup

4 hoursFree Cancellation

(5)

from $820

Experience Chicago like never before—and see more of the sights in less time—on this immersive bicycle tour. Ride the walking- and cycling-only Chicago Lakefront Trail to and through the city’s beautiful beaches, parks and lagoons. See the coast of Lake Michigan and the one-of-a-kind Chicago skyline, plus bustling Navy Pier, popular North Avenue Beach, the 35-acre Lincoln Park Zoo and Conservatory, and much more. The use of a bike and helmet is included.

Special Offer

Chicago Amazing Lakefront Bike Tour

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 daysFree Cancellation

3.5

(2)

from $5

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Chicago Architecture River Cruise

Kelli_R, Jul 2026

Family friendly tour

We had a wonderful time with our kids on the River architecture cruise. Despite having lived in the Midwest for 15 years, we had never done it. The kids both thought it was interesting (as did we!) and we got lucky with a gorgeous day. Our “cruise director” was Eric and he was great - informative and funny and left some time for us to just admire the buildings.

Chicago River 90-Minute Architecture Tour

Madison_G, Jul 2026

Unbeatable views of city with history!

Melissa, our tour guide was highly knowledgeable in all things architecture and history of the city. She also never tired from reciting the same spiel that she probably does numerous times a day. You learn all kinds of things that you probably wouldn’t have otherwise. We took the 8pm tour in the middle of July and we got to see the sunset and all the buildings lit up which was perfect.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Chad_W, Jul 2026

Very impressed!

The tour was beautiful and and the guide, Molly, was exceptional! She seemed quite knowledgeable and you could tell she loves the city and it's architecture. It was very cool and for my 16 year old daughter to be as impressed as she was, that's something!

Chicago Crime and Mob Bus Tour

Henry_C, Jul 2026

The host was fantastic...

The host was fantastic and his delivery was spot on. He kept it lighthearted and funny while still making it informative and interesting. I thought this was going to be a gangster tour with a focus on Al Capone, but they presented generations of crime stories, from the Chicago’s origins to the Crack dealing McDonalds employees. I was young when the Tylenol scare occurred and to go past the Walgreens where it happened was also interesting. The only negative feedback I can give is the bus broke down outside of Harry Cary’s and we had to figure out how to get back to the neighborhood we started in. Obviously this was a one off and I would not judge to tour by an unforeseen. Great tour and worth the price of admission.

Chicago Sightseeing River and Lake Cruise

Laurie_M, Jul 2026

Love Love Love First Lady

Wow! Prepare to see gorgeous views of the City! Our tour guide was a fun, walking, talking, singing encyclopedia of Chicago history. Welcomed breaks allowed our brains to rest up before the next heaping helping of river, lake, & architectural facts & folklore. Kids ages 8-10 loved it, particularly the stories about Montgomery Ward. Fellow passengers were friendly. Very nice all the way around.

Chicago Lake and River Architecture Tour

Kathleen_M, Jul 2026

Great river tour?

This tour was everything people said it would be. The boat went through the locks to Lake Michigan, very exciting. Our tour guide was very knowledgeable about the skyscrapers and their history. She also gave us a restaurant recommendation - The Chicago Brewhouse on the Riverwalk. We had a great time and dinner! Thank you!

Original Chicago Architecture Interiors Tour: Dazzling Interiors

KATHLEEN_M, Jul 2026

Awesome way to spend few hours!!

I live in the Chicagoland area. We just wanted to go to the city and do something different. This tour was awesome. Not too much walking, got to go in a lot of buildings with air-conditioning so the weather was not too much of an issue. We just loved it. Learned so much about buildings that we see every day but I’ve never actually gone into. Highly recommend it for locals as well as out-of-towners. Kate was an awesome guide if you can get her I’d recommend that as well.

Lake Michigan Sunset Cruise in Chicago

Lesley_H, Jul 2026

Don’t miss this one

Bookings are full, so get there at least a half hour before boarding to ensure you get seats together. Absolutely wonderful experience. Guide explains the history of buildings on the Chicago river then Boat goes to Lake Michigan for the sunset. You’re able to see Navy pier Hancock building, Sirrius (Willis) tower and many other Chicago landmarks coming back. The sky is beautifully lit.

Chicago Architecture Center River Cruise aboard First Lady

Michelle_K, Jul 2026

Very enjoyable tour!

I've wanted to do this tour for several years. It did not disappoint. We went right away in the morning (9:30 AM) and it was cool enough to enjoy and the boat wasn't croweded. The docent who volunteered was very knowledgeable and we loved hearing the history of each of the buildings. Great tour if you are even mildly interested in history and architecture and the river is beautiful!

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

Melinda_S, Jun 2026

Great architecture and delicious eats!

What a fun day of exploring the architecture and food of Chicago. We visited several historical buildings and learned more about the history from our tour guide Chad. It was a hot one but we ducked in and out of the AC and tried Chicago dogs, beef dips and deep dish pizza. It was just my husband and I on the tour so we were able to spend more time at places of interest like the Chicago Symphony performing at Millennium Park, an unexpected suprise! Highly recommended tour.