Top Chicago Tours & Sightseeing

Q: What are the best options for Chicago Tours & Sightseeing?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Chicago Tours & Sightseeing are: Chicago Lakefront Electric Bike Tour Frank Lloyd Wright Oak Park Architecture Tour from Chicago Chicago-Style Holiday Hike: Festive Food and Walking Tour Chicago River Floating Tiki Bar Cruise Friday and Saturday Chicago Loop Walking Tour

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

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Chicago Tours & Sightseeing 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 Tours & Sightseeing have Instant Confirmation?

Chicago Tours & Sightseeing with Instant Confirmation include: Chicago Exotic Auto Experience Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens Chicago 6-Hour City Tour by Sedan Private 45-Minute Chicago Skyline Helicopter Tour 4-Hour Chicago City Tour by SUV View all Tours with Instant Confirmation →

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

No problem. These Chicago Tours & Sightseeing include Hotel Pickup: Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens Private Chicago City Minibus Tour Chicago 6-Hour City Tour by Sedan 4-Hour Chicago City Tour by SUV Private City Tour 6-10ppl 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 →

Field Museum of Natural History Early Access Ticket

Visit the Field Museum like a VIP on this one- hour early access VIP tour. Head inside the Field Museum at 8am before it opens …More

4.7 (57)

Field Museum of Natural History Early Access Ticket

Visit the Field Museum like a VIP on this one- hour early access VIP tour. Head inside the Field Museum at 8am before it opens...

2 to 4 hours Free Cancellation

4.7 (57)

from
$73

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

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all …More

4.9 (1,046)

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all...

3 hours Free Cancellation

4.9 (1,046)

from
$68

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

Chicago Gangsters and Ghosts Minibus Tour

Uncover the notorious history of Chicago's gangster era on this immersive bus tour that takes you through the city's most infamous landmarks. Visit the Palmer …More

4.9 (18)

Chicago Gangsters and Ghosts Minibus Tour

Uncover the notorious history of Chicago's gangster era on this immersive bus tour that takes you through the city's most infamous landmarks. Visit the Palmer...

2 hours Free Cancellation

4.9 (18)

from
$65

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise. Witness the stunning skyline as you glide across the water, leading up to …More

4.5 (17)

Chicago Fireboat Fireworks Cruise

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise. Witness the stunning skyline as you glide across the water, leading up to...

1 hour 30 minutes Free Cancellation

4.5 (17)

from
$63

Lake Michigan Fireworks Cruise in Chicago

No city embraces summer quite like Chicago. Join in the celebration with friends and family on this epic fireworks cruise. Get up-close and personal every …More

4.5 (127)

Lake Michigan Fireworks Cruise in Chicago

No city embraces summer quite like Chicago. Join in the celebration with friends and family on this epic fireworks cruise. Get up-close and personal every...

2 to 3 hours

4.5 (127)

from
$60

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

Chicago Hauntings Original Ghost Bus Tour

Often imitated but never matched, this 3 hour ghost bus tour with stops remains the "Best of Chicago" since its founding 23 years ago by …More

4.1 (136)

Chicago Hauntings Original Ghost Bus Tour

Often imitated but never matched, this 3 hour ghost bus tour with stops remains the "Best of Chicago" since its founding 23 years ago by...

3 hours Free Cancellation

4.1 (136)

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