Top Chicago City Tours

Q: What are the best options for Chicago City Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Chicago City Tours are: River North Food Walking Tour Chicago Walking Tour: Modern Architecture Chicago Walking Tour: Connecting Past and Present Chicago Scenic Driving Tour Chicago City Private Tours

Q: What are the best kid-friendly options for Chicago City Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Chicago City Tours are: 5-Day Tour of Superior, Huron and Michigan from Chicago Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago Private and All-Inclusive Tour of Chicago Chicago Helicopter Tour: City to Shoreline Chicago Small Group City Tour View all kid-friendly Tours →

Q: Which Chicago City Tours have Instant Confirmation?

Chicago City Tours with Instant Confirmation include: Chicago Exotic Auto Experience Chicago 6-Hour City Tour by Sedan Private 45-Minute Chicago Skyline Helicopter Tour 4-Hour Chicago City Tour by SUV Private City Tour 6-10ppl View all Tours with Instant Confirmation →

Q: I need a ride! Which Chicago City Tours have Hotel Pickup?

No problem. These Chicago City Tours include Hotel Pickup: Chicago 6-Hour City Tour by Sedan 4-Hour Chicago City Tour by SUV Private City Tour 6-10ppl Private and All-Inclusive Tour of Chicago 4 Hours of Chicago City Tour Sedan View all Tours with Hotel Pickup →

Q: Got any more Chicago trip ideas?

We sure do. Check out our curated lists of hand-picked Chicago Tours. Top 10 Chicago 2026 Senior-friendly tours Chicago The best tours and activities for culture lovers in Chicago Top Day Trips from Chicago Things to do in Chicago this summer View all Chicago Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Chicago?

Based on our sales data over the past year, the most popular styles of tours and activities in Chicago are: Chicago Luxury & Special Occasions Chicago Luxury Tours Chicago Tours & Sightseeing Chicago Cruises, Sailing & Water Tours Chicago Boat Tours View all tour styles in Chicago →

Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views …More

5.0 (27)

Chicago Sunset Segway Tour

Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views...

1 hour 30 minutes Free Cancellation

5.0 (27)

from
$75

This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the …More

4.9 (52)

Chicago Insider Segway Tour

This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the...

2 hours Free Cancellation

4.9 (52)

from
$72

Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings

Recently voted one of Cool Shore Excursions's top food tours in the US. Discover the sweet side of the Windy City on the Underground Donut …More

5.0 (1,573)

Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings

Recently voted one of Cool Shore Excursions's top food tours in the US. Discover the sweet side of the Windy City on the Underground Donut...

2 hours Free Cancellation

5.0 (1,573)

from
$70

Chicago Landmarks and Museum Campus Small Group Segway Tour

Looking for fun things to do in Chicago? Explore the city with one of your professional guides on a scenic 6-7 mile tour. Begin your …More

5.0 (236)

Chicago Landmarks and Museum Campus Small Group Segway Tour

Looking for fun things to do in Chicago? Explore the city with one of your professional guides on a scenic 6-7 mile tour. Begin your...

2 hours Free Cancellation

5.0 (236)

from
$70

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have …More

4.7 (145)

Lakefront Segway Tour in Chicago

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have...

1 hour 30 minutes Free Cancellation

4.7 (145)

from
$70

Chicago West Loop Sweet Treats Food Tour: Donuts, Cookies, & More

We begin at a local shop synonymous for their quality donuts––Do-Rite Donuts. From there we’ll walk the Randolph corridor, learning about the history of Chicago’s …More

5.0 (95)

Chicago West Loop Sweet Treats Food Tour: Donuts, Cookies, & More

We begin at a local shop synonymous for their quality donuts––Do-Rite Donuts. From there we’ll walk the Randolph corridor, learning about the history of Chicago’s...

2 hours Free Cancellation

5.0 (95)

from
$70

This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will …More

5.0 (15)

Chicago Lakefront Electric Bike Tour

This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will...

45 to 60 minutes Free Cancellation

5.0 (15)

from
$69

This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the Magnificent Mile, and then heading into the Gold …More

5.0 (131)

Downtown Chicago Walking Pizza Tour

This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the Magnificent Mile, and then heading into the Gold...

2 to 3 hours Free Cancellation

5.0 (131)

from
$69

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Looking for fun things to do in Chicago? Look no further! Join one of our professional guides on a scenic 6-8 mile Chicago Segway tour. …More

5.0 (394)

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Looking for fun things to do in Chicago? Look no further! Join one of our professional guides on a scenic 6-8 mile Chicago Segway tour....

2 hours Free Cancellation

5.0 (394)

from
$67

Luxury Minibus Chicago City Tour with Architecture Cruise Upgrade

Experience the ultimate Windy City adventure on Chicago’s luxury guided minibus tour! Explore 20+ top landmarks with curated photo stops at Cloud Gate "The Bean", …More

4.9 (21)

Luxury Minibus Chicago City Tour with Architecture Cruise Upgrade

Experience the ultimate Windy City adventure on Chicago’s luxury guided minibus tour! Explore 20+ top landmarks with curated photo stops at Cloud Gate "The Bean",...

2 hours Free Cancellation

4.9 (21)

from
$65

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists. …More

4.9 (56)

Chicago Loop Walking Tour

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists....

2 hours Free Cancellation

4.9 (56)

from
$60

Bike Tour of Chicago's Lakefront Neighborhoods

This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence …More

4.9 (247)

Bike Tour of Chicago's Lakefront Neighborhoods

This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence...

3 hours Free Cancellation

4.9 (247)

from
$59

Chicago's Ultimate City Bike Tour of Top Downtown Attractions

Get acquainted with Chicago’s most iconic landmarks on this riotous guided Chicago bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city …More

5.0 (274)

Chicago's Ultimate City Bike Tour of Top Downtown Attractions

Get acquainted with Chicago’s most iconic landmarks on this riotous guided Chicago bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city...

3 hours Free Cancellation

5.0 (274)

from
$59

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, …More

5.0 (1)

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,...

3 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$58

Chicago Architecture Center River Cruise aboard First Lady

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only …More

5.0 (7,634)

Chicago Architecture Center River Cruise aboard First Lady

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only...

1 hour 30 minutes

5.0 (7,634)

from
$57

Chicago River Spectacular Fireworks Show and Tiki Bar Cruise

Fireworks Cruise Aboard Island Time – See the Sparks Fly the Island Party Way! Experience Chicago’s dazzling fireworks like never before—from the deck of our …More

4.5 (35)

Chicago River Spectacular Fireworks Show and Tiki Bar Cruise

Fireworks Cruise Aboard Island Time – See the Sparks Fly the Island Party Way! Experience Chicago’s dazzling fireworks like never before—from the deck of our...

1 hour 30 minutes

4.5 (35)

from
$54

Chicago City Tour with Architecture River Cruise Option

Uncover the Windy City on Chicago’s premier guided minibus tour! Discover 20+ top landmarks with photo stops at Cloud Gate "The Bean", Museum Campus, & …More

4.8 (728)

Chicago City Tour with Architecture River Cruise Option

Uncover the Windy City on Chicago’s premier guided minibus tour! Discover 20+ top landmarks with photo stops at Cloud Gate "The Bean", Museum Campus, &...

2 to 4 hours Free Cancellation

4.8 (728)

from
$50

Uncover the Windy City on Chicago’s premier guided minibus tour! Discover 20+ top landmarks with curated photo stops at Cloud Gate ("The Bean"), Museum Campus, …More

4.9 (689)

Chicago City Minibus Tour

Uncover the Windy City on Chicago’s premier guided minibus tour! Discover 20+ top landmarks with curated photo stops at Cloud Gate ("The Bean"), Museum Campus,...

2 hours Free Cancellation

4.9 (689)

from
$50

Enjoy the car-free lakefront trail and explore Chicago’s beaches, parks, lagoons, This tour offers a diverse mix of nature and attractions. Top sights include: The …More

3.6 (8)

Chicago Amazing Lakefront Bike Tour

Enjoy the car-free lakefront trail and explore Chicago’s beaches, parks, lagoons, This tour offers a diverse mix of nature and attractions. Top sights include: The...

1 hour 30 minutes Free Cancellation

3.6 (8)

from
$49

Best of Chicago: Premium Small Group City Tour

Discover Chicago on a 2.5-hour premium small group city tour combining landmark architecture, public art, and lakefront scenery. Begin along the Magnificent Mile and Chicago …More

5.0 (48)

Best of Chicago: Premium Small Group City Tour

Discover Chicago on a 2.5-hour premium small group city tour combining landmark architecture, public art, and lakefront scenery. Begin along the Magnificent Mile and Chicago...

2 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (48)

from
$48