Top Chicago Historical & Heritage Tours

Q: Which Chicago Historical & Heritage Tours have Instant Confirmation?

Chicago Historical & Heritage Tours with Instant Confirmation include: Chicago Crime and Mob Bus Tour Chicago City Minibus Tour Chicago Night Crimes Tour by Bus Original Chicago Architecture Interiors Tour: Dazzling Interiors Chicago's Original Gangster Tour by Bus View all Tours with Instant Confirmation →

Q: Which Chicago Historical & Heritage Tours have Free Cancellation?

Chicago Historical & Heritage Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include: Chicago Crime and Mob Bus Tour Chicago City Minibus Tour Chicago Night Crimes Tour by Bus Original Chicago Architecture Interiors Tour: Dazzling Interiors Chicago's Original Gangster Tour by Bus View all Tours with Free Cancellation →

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

No problem. These Chicago Historical & Heritage Tours include Hotel Pickup: The Bear Private Pedicab Food Tour of Chicago Chicago Private Neighborhoods Tour to Lincoln and Hyde Park Lincoln Park Secrets: Private Enchanted Pedicab History Tour One Day Galena and Dubuque Tour from Chicago Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens 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 →

Chicago Private Neighborhoods Tour to Lincoln and Hyde Park

Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares local …More

5.0 (1)

Chicago Private Neighborhoods Tour to Lincoln and Hyde Park

Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares local...

4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$77

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

The Art Institute in Chicago Highlights Tour & Photoshoot

Discover the Art Institute in a unique way that blends art, storytelling, and photography. After a warm welcome, we'll head inside with tickets included & …More

5.0 (5)

The Art Institute in Chicago Highlights Tour & Photoshoot

Discover the Art Institute in a unique way that blends art, storytelling, and photography. After a warm welcome, we'll head inside with tickets included &...

1 hour 15 minutes Free Cancellation

5.0 (5)

from
$101

Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking …More

5.0 (7)

Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking...

2 hours Free Cancellation

5.0 (7)

from
$50

Explore the Historic Old Post Office in Chicago

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once …More

5.0 (27)

Explore the Historic Old Post Office in Chicago

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once...

1 hour 30 minutes Free Cancellation

5.0 (27)

from
$15

Prairie Avenue Haunted History Tour and Ghost Hunt

Chicago's original Millionaire's Row, meet the ghosts of the Gilded Age. Marshall Field, George Pullman, Philip Armour, and many more used to live in this …More

5.0 (12)

Prairie Avenue Haunted History Tour and Ghost Hunt

Chicago's original Millionaire's Row, meet the ghosts of the Gilded Age. Marshall Field, George Pullman, Philip Armour, and many more used to live in this...

2 hours 20 minutes

5.0 (12)

from
$44

Haunted Chicago: Lincoln Park Ghost & History Walking Tour

This isn’t just a ghost tour, it’s a story-driven walk through one of Chicago’s most haunted landscapes, where real history and local legend collide. Unlike …More

4.3 (13)

Haunted Chicago: Lincoln Park Ghost & History Walking Tour

This isn’t just a ghost tour, it’s a story-driven walk through one of Chicago’s most haunted landscapes, where real history and local legend collide. Unlike...

1 hour 30 minutes Free Cancellation

4.3 (13)

from
$30

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This …More

5.0 (5)

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This...

2 hours 30 minutes Free Cancellation

5.0 (5)

from
$43

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Bronzeville, led by Historian Dilla, …More

5.0 (2)

2 Hour Bronzeville, Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Bronzeville, led by Historian Dilla,...

2 hours Free Cancellation

5.0 (2)

from
$45

Roundtrip Shuttle to South Side and Obama Presidential Center

Discover more of Chicago beyond downtown with this convenient South Side open-top shuttle transfer. Travel from central Chicago to some of the city’s most important …More

4.5 (20)

Roundtrip Shuttle to South Side and Obama Presidential Center

Discover more of Chicago beyond downtown with this convenient South Side open-top shuttle transfer. Travel from central Chicago to some of the city’s most important...

30 minutes Free Cancellation

4.5 (20)

from
$10

The Experience is more than a food tour. It is an immersive cultural experience that combines food, history, architecture, and storytelling in one of Chicago’s …More

5.0 (6)

Explore Chicago Black Culinary Heritage

The Experience is more than a food tour. It is an immersive cultural experience that combines food, history, architecture, and storytelling in one of Chicago’s...

2 hours 45 minutes Free Cancellation

5.0 (6)

from
$75

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

Explore haunted Chicago at your own pace and schedule. Go anytime. Why take this tour? -It's like an in person tour guide, only it's on …More

4.8 (6)

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

Explore haunted Chicago at your own pace and schedule. Go anytime. Why take this tour? -It's like an in person tour guide, only it's on...

60 to 75 minutes Free Cancellation

4.8 (6)

from
$10

Chicago in Spanish. Architecture. Mafia, Interiors, Underground

Discover the real Chicago with those who really know it! At ChicaGo Turismo we transform a simple tour into an unforgettable experience. More than visiting …More

5.0 (8)

Chicago in Spanish. Architecture. Mafia, Interiors, Underground

Discover the real Chicago with those who really know it! At ChicaGo Turismo we transform a simple tour into an unforgettable experience. More than visiting...

3 hours Free Cancellation

5.0 (8)

from
$45

Our Original Bus Tour is a deep dive into Chicago's most notorious era. Taking you to neighborhood gems you may not find on your own, …More

5.0 (4)

Original Chicago Prohibition Bus Tour

Our Original Bus Tour is a deep dive into Chicago's most notorious era. Taking you to neighborhood gems you may not find on your own,...

Free Cancellation

5.0 (4)

from
$55

Chicago Riverwalk Self-Guided Walking Tour

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city second Lakefront', the Riverwalk contains restaurants during the summer …More

4.4 (8)

Chicago Riverwalk Self-Guided Walking Tour

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city second Lakefront', the Riverwalk contains restaurants during the summer...

1 to 2 hours Free Cancellation

4.4 (8)

from
$13

Chicago Art Heist: Millennium Park Puzzle Adventure

You just stole Edward Hopper's Nighthawks from the Art Institute of Chicago. Now you need to disappear into the city before anyone notices. This self-guided …More

3.9 (11)

Chicago Art Heist: Millennium Park Puzzle Adventure

You just stole Edward Hopper's Nighthawks from the Art Institute of Chicago. Now you need to disappear into the city before anyone notices. This self-guided...

1 hour 35 minutes Free Cancellation

3.9 (11)

from
$8

Chicago Millennium Park Self-Guided Walking Tour

Enjoy moving at your own pace through Chicago's Millennium Park with an app as your guide. You and your private party can stop or start …More

4.6 (5)

Chicago Millennium Park Self-Guided Walking Tour

Enjoy moving at your own pace through Chicago's Millennium Park with an app as your guide. You and your private party can stop or start...

1 to 2 hours Free Cancellation

4.6 (5)

from
$13

Chicago Chinatown: Dragon Kings Puzzle Adventure

The year is 1375, and a devastating drought grips China. The Emperor sends you, his Imperial Advisor, to find the four Dragon Kings, rulers of …More

3.8 (10)

Chicago Chinatown: Dragon Kings Puzzle Adventure

The year is 1375, and a devastating drought grips China. The Emperor sends you, his Imperial Advisor, to find the four Dragon Kings, rulers of...

48 to 78 minutes Free Cancellation

3.8 (10)

from
$8

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

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