Top Chicago Tours & Sightseeing

Q: Which Chicago Tours & Sightseeing have Instant Confirmation?

Chicago Tours & Sightseeing with Instant Confirmation include: Hyde Park Walking Tour History Race and Urban Change Continental US Train Zephyr Adventure CA -CO - Il Chicago Self-Guided Audio Tour Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour Chicago Scav Hunt - An App-Guided Adventure 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 Night Skyline and Lakefront Scenic Tour Best of Chicago: Premium Small Group City Tour Skyline Lakefront and Millennium Park Chicago Private Day Tour Chicago Private Neighborhoods Tour to Lincoln and Hyde Park Frank Lloyd Wright Oak Park Architecture Tour from Chicago 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-Style Holiday Hike: Festive Food and Walking Tour

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holiday Hike, a 3-hour guided …More

5.0 (77)

Chicago-Style Holiday Hike: Festive Food and Walking Tour

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holiday Hike, a 3-hour guided...

3 hours Free Cancellation

5.0 (77)

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$85

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)

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$85

Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables, …More

4.8 (4)

Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables,...

2 hours

4.8 (4)

from
$87

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Taste all of Chicago’s classic eats on this 4 1/2 hr Adults-only guided food & bicycle tour! Join the expert guides of Bobby’s Bike Hike, …More

5.0 (761)

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Taste all of Chicago’s classic eats on this 4 1/2 hr Adults-only guided food & bicycle tour! Join the expert guides of Bobby’s Bike Hike,...

4 hours 30 minutes Free Cancellation

5.0 (761)

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$89

Enjoy Chicago’s only bus guided neighborhood pizza tour. Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the …More

4.9 (489)

Chicago Pizza Tour

Enjoy Chicago’s only bus guided neighborhood pizza tour. Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the...

3 hours 30 minutes Free Cancellation

4.9 (489)

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$89

On our 3 hour food walking tour of Chicago, you will taste delectable foods from 5 different delicious places. Tease your tastebuds as you savor …More

4.6 (96)

River North Food Walking Tour

On our 3 hour food walking tour of Chicago, you will taste delectable foods from 5 different delicious places. Tease your tastebuds as you savor...

3 hours Free Cancellation

4.6 (96)

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$89

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

Lincoln Park Secrets: Private Enchanted Pedicab History Tour

Our knowledgeable and licensed guide will drive you between each location in an open air motorized pedicab! Also a great option for anyone with mobility …More

5.0 (1)

Lincoln Park Secrets: Private Enchanted Pedicab History Tour

Our knowledgeable and licensed guide will drive you between each location in an open air motorized pedicab! Also a great option for anyone with mobility...

60 to 70 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$90

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, …More

4.8 (30)

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy,...

1 hour 15 minutes

4.8 (30)

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$91

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)

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$98

Chicago's West Side Foodie Ride Bike Tour

Take a detour off the beaten path, and explore the flavors of Chicago’s delicious West Side with Bobbys's Bike Hike & Food Tours, America's longest …More

5.0 (113)

Chicago's West Side Foodie Ride Bike Tour

Take a detour off the beaten path, and explore the flavors of Chicago’s delicious West Side with Bobbys's Bike Hike & Food Tours, America's longest...

4 hours Free Cancellation

5.0 (113)

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$99

Chicago Full-Day Walking Food Tour with Free Bike or Kayak Rental

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary …More

5.0 (3)

Chicago Full-Day Walking Food Tour with Free Bike or Kayak Rental

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary...

5 hours Free Cancellation

5.0 (3)

from
$99

Chicago Architecture River Tour & Hop-on Hop-off Sightseeing Tour

Save 20% when you bundle these two iconic Chicago experiences! Discover Chicago by road and river with a 48-hour Hop-on Hop-off Ticket and Shoreline Architecture …More

4.5 (46)

Chicago Architecture River Tour & Hop-on Hop-off Sightseeing Tour

Save 20% when you bundle these two iconic Chicago experiences! Discover Chicago by road and river with a 48-hour Hop-on Hop-off Ticket and Shoreline Architecture...

2 hours Free Cancellation

4.5 (46)

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$99

Let’s take photos at one of Chicago’s most famous spots - the bright red CHICAGO sign at the Chicago Theatre! During this 30-40 minute photo …More

5.0 (4)

Express Chicago Photo Tour of Landmarks

Let’s take photos at one of Chicago’s most famous spots - the bright red CHICAGO sign at the Chicago Theatre! During this 30-40 minute photo...

30 to 40 minutes Free Cancellation

5.0 (4)

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$99

Downtown Chicago City Tour In a Lamborghini[60 Minute Experience]

Experience Chicago in unparalleled style with a 10-mile cruise through the city in a luxury or exotic vehicle. Glide through iconic streets, turning heads at …More

5.0 (2)

Downtown Chicago City Tour In a Lamborghini[60 Minute Experience]

Experience Chicago in unparalleled style with a 10-mile cruise through the city in a luxury or exotic vehicle. Glide through iconic streets, turning heads at...

45 to 60 minutes

5.0 (2)

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$99

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

Immerse yourself in Chicago's rich history and vibrant culinary scene on this captivating walking tour. Discover the city's iconic architecture and Prohibition-era charm while indulging …More

4.9 (1,444)

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

Immerse yourself in Chicago's rich history and vibrant culinary scene on this captivating walking tour. Discover the city's iconic architecture and Prohibition-era charm while indulging...

4 hours 30 minutes Free Cancellation

4.9 (1,444)

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$101

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)

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$101

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)

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$109

Chicago's Fireworks Show aboard Tall Ship Windy!

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in …More

4.8 (24)

Chicago's Fireworks Show aboard Tall Ship Windy!

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in...

1 hour 30 minutes

4.8 (24)

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$114

The Blue-Collar side of Chicago many call it! This tour will show The Ford Factory, home of the steel mills, the blue-collar neighborhoods and many …More

4.7 (49)

Chicago Tour South Side

The Blue-Collar side of Chicago many call it! This tour will show The Ford Factory, home of the steel mills, the blue-collar neighborhoods and many...

4 hours Free Cancellation

4.7 (49)

from
$125