Top Chicago Walking & Biking Tours

Q: Which Chicago Walking & Biking Tours have Instant Confirmation?

Chicago Walking & Biking Tours with Instant Confirmation include: Chicago Favorites Ultimate Food and Walking Tour Original Chicago Architecture Interiors Tour: Dazzling Interiors Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings Chicago in a Day Walking Tour: Food, History & Architecture Chicago's Chinatown Food and Walking Tour View all Tours with Instant Confirmation →

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

No problem. These Chicago Walking & Biking Tours include Hotel Pickup: Chicago City Private Tours 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 →

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

On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hancock …More

5.0 (3)

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

On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hancock...

3 hours Free Cancellation

5.0 (3)

from
$109

Private Wicker Park and Bucktown Walking Tour

This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time …More

5.0 (3)

Private Wicker Park and Bucktown Walking Tour

This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time...

2 hours 30 minutes Free Cancellation

5.0 (3)

from
$195

Best Chinatown Food and Walking Tour in town! The Chicago’s Chinatown Food and Walking Tour is a 3-hour immersive culinary and cultural experience designed to …More

5.0 (3)

Taste of Chicago's Chinatown Food Tours

Best Chinatown Food and Walking Tour in town! The Chicago’s Chinatown Food and Walking Tour is a 3-hour immersive culinary and cultural experience designed to...

3 hours Free Cancellation

5.0 (3)

from
$85

Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent …More

5.0 (3)

Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent...

7 days Free Cancellation

5.0 (3)

from
$11

West Town Hot Spots Tour By Studio W.I.P.

Our tours are not only personable (due to small group sizes), but also create an immersive experience with our knowledge and expertise in street art. …More

5.0 (3)

West Town Hot Spots Tour By Studio W.I.P.

Our tours are not only personable (due to small group sizes), but also create an immersive experience with our knowledge and expertise in street art....

90 to 105 minutes Free Cancellation

5.0 (3)

from
$27

️ Chicago Instagram Walking Tour (Private & All- Inclusive)

Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a …More

5.0 (2)

️ Chicago Instagram Walking Tour (Private & All- Inclusive)

Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a...

4 hours Free Cancellation

5.0 (2)

from
$236

Field Museum of Natural History Chicago Tour with Tickets

Skip the lines and uncover ancient wonders at Chicago’s Field Museum, home to SUE, the world’s most complete T. rex. Marvel at dazzling artifacts, real …More

5.0 (2)

Field Museum of Natural History Chicago Tour with Tickets

Skip the lines and uncover ancient wonders at Chicago’s Field Museum, home to SUE, the world’s most complete T. rex. Marvel at dazzling artifacts, real...

2 hours Free Cancellation

5.0 (2)

from
$113

Discover the streets of Lincoln Park, Chicago, and the Magnificent Lake Front on a high-quality electric bike rental from E-Z Rider Bike Shop. Our e-bikes …More

5.0 (2)

Electric Bike Tours in Lincoln Park

Discover the streets of Lincoln Park, Chicago, and the Magnificent Lake Front on a high-quality electric bike rental from E-Z Rider Bike Shop. Our e-bikes...

2 hours 30 minutes Free Cancellation

5.0 (2)

from
$85

Step into the shadows of Chicago’s past on this adults-only haunted pub crawl, where ghost stories, historic landmarks, and legendary nightlife collide. Beginning near the …More

5.0 (1)

Burning Spirits Haunted Pub Crawl

Step into the shadows of Chicago’s past on this adults-only haunted pub crawl, where ghost stories, historic landmarks, and legendary nightlife collide. Beginning near the...

2 hours Free Cancellation

5.0 (1)

from
$35

Chicago Photography Masterclass Private Photography Lesson

This tour is special because it combines a personalized street and night tour experience with expert photography guidance in Chicago. You’ll explore both iconic landmarks …More

5.0 (1)

Chicago Photography Masterclass Private Photography Lesson

This tour is special because it combines a personalized street and night tour experience with expert photography guidance in Chicago. You’ll explore both iconic landmarks...

3 hours Free Cancellation

5.0 (1)

from
$110

Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding …More

5.0 (1)

Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding...

4 hours Free Cancellation

5.0 (1)

from
$179

Hyde Park Walking Tour History Race and Urban Change

Discover the rich history and dynamic transformation of Hyde Park on this engaging walking tour. Delve into the neighborhood's evolution from a lakeside retreat for …More

5.0 (1)

Hyde Park Walking Tour History Race and Urban Change

Discover the rich history and dynamic transformation of Hyde Park on this engaging walking tour. Delve into the neighborhood's evolution from a lakeside retreat for...

3 hours Free Cancellation

5.0 (1)

from
$5

2 Hours Chicago Architecture Tour - Skyscrapers 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 …More

5.0 (1)

2 Hours Chicago Architecture Tour - Skyscrapers 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...

2 hours Free Cancellation

5.0 (1)

from
$89

Experience the authentic flavors of Chinatown on a 3-hour guided food tour curated by Chicago Tribune Good Eating Award winner Z.J. Tong. As you explore …More

5.0 (1)

Chinatown Food Tour

Experience the authentic flavors of Chinatown on a 3-hour guided food tour curated by Chicago Tribune Good Eating Award winner Z.J. Tong. As you explore...

3 hours Free Cancellation

5.0 (1)

from
$98

Private History and Architecture of Chicago Loop Walking Tour

This is a private walking tour with your group and expert tour guide Dave Lineal. Different tour start times available upon request. I am happy …More

5.0 (1)

Private History and Architecture of Chicago Loop Walking Tour

This is a private walking tour with your group and expert tour guide Dave Lineal. Different tour start times available upon request. I am happy...

2 hours 30 minutes Free Cancellation

5.0 (1)

from
$180

Private Cultural Walking Tour in Chicago with Lakefront Landmarks

This private cultural walking tour in Chicago presents the city’s architectural heritage and lakefront legacy. You will begin in Millennium Park, where public art reflects …More

5.0 (1)

Private Cultural Walking Tour in Chicago with Lakefront Landmarks

This private cultural walking tour in Chicago presents the city’s architectural heritage and lakefront legacy. You will begin in Millennium Park, where public art reflects...

2 hours Free Cancellation

5.0 (1)

from
$349

Private Christmas Walking Tour in Chicago with Christkindlmarket

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where architectural landmarks are …More

5.0 (1)

Private Christmas Walking Tour in Chicago with Christkindlmarket

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where architectural landmarks are...

2 hours Free Cancellation

5.0 (1)

from
$469

Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit

Channel your inner Sherlock Holmes in this murder mystery hunt around The Chicago Loop. In the “Murder in The Chicago Loop” transports you to the …More

5.0 (1)

Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit

Channel your inner Sherlock Holmes in this murder mystery hunt around The Chicago Loop. In the “Murder in The Chicago Loop” transports you to the...

1 hour Free Cancellation

5.0 (1)

from
$59

Wicker Park Walking Tour History Trivia and Local Flavors

Discover the vibrant Wicker Park neighborhood as you stroll from the Polish Triangle through the Milwaukee Avenue shopping and dining district. This guided walking tour …More

5.0 (1)

Wicker Park Walking Tour History Trivia and Local Flavors

Discover the vibrant Wicker Park neighborhood as you stroll from the Polish Triangle through the Milwaukee Avenue shopping and dining district. This guided walking tour...

90 to 120 minutes Free Cancellation

5.0 (1)

from
$40

Chicago Highlights Private Walking Tour with a Guide

Immerse yourself in Chicago's architectural heritage on an exclusive walking tour, delving into the city's iconic structures and Art Deco gems. Begin your intimate journey …More

5.0 (1)

Chicago Highlights Private Walking Tour with a Guide

Immerse yourself in Chicago's architectural heritage on an exclusive walking tour, delving into the city's iconic structures and Art Deco gems. Begin your intimate journey...

2 hours Free Cancellation

5.0 (1)

from
$46

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Chicago Walking & Biking Tours?

What are the best kid-friendly options for Chicago Walking & Biking Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Chicago Walking & Biking Tours are:

View all kid-friendly Tours →

Which Chicago Walking & Biking Tours have Instant Confirmation?

Which Chicago Walking & Biking Tours have Free Cancellation?

Chicago Walking & Biking Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Chicago Walking & Biking Tours have Hotel Pickup?

Got any more Chicago trip ideas?

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