Top Chicago Luxury Tours

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

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Chicago Luxury Tours are: Chicago Movie Locations Tour Private Chicago City Minibus Tour Explore Chicago Black Culinary Heritage Chicago Architecture Gilded Interiors Walking Tour City Cruises Chicago: Premier Lake Michigan Brunch Cruise

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

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Chicago Luxury Tours are: Continental US Train Zephyr Adventure CA -CO - Il Roundtrip Shuttle to South Side and Obama Presidential Center Explore Chicago’s Indoor Mushroom Farm Experience Frank Lloyd Wright Robie House Admission West Town Hot Spots Tour By Studio W.I.P. View all kid-friendly Tours →

Q: Which Chicago Luxury Tours have Instant Confirmation?

Chicago Luxury Tours 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 Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour View all Tours with Instant Confirmation →

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

No problem. These Chicago Luxury Tours 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 Family Food and Bike Tour with Top Attractions

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past …More

4.9 (99)

Chicago Family Food and Bike Tour with Top Attractions

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past...

4 hours Free Cancellation

4.9 (99)

from
$79

Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours have ranked …More

4.9 (853)

Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours have ranked...

3 hours Free Cancellation

4.9 (853)

from
$80

Chicago: Gangsters and Food Tasting Walking Tour

Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Learn about Chicago's world-famous cuisine …More

4.7 (49)

Chicago: Gangsters and Food Tasting Walking Tour

Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Learn about Chicago's world-famous cuisine...

2 hours Free Cancellation

4.7 (49)

from
$80

Art Institute of Chicago Private Expert Guided Tour

Let our expert local guides share their passion with you for The Art Institute of Chicago on this private 2 hour tour. As you traverse …More

5.0 (137)

Art Institute of Chicago Private Expert Guided Tour

Let our expert local guides share their passion with you for The Art Institute of Chicago on this private 2 hour tour. As you traverse...

2 hours Free Cancellation

5.0 (137)

from
$80

Chicago Loop Food Tour: Taste the Most Iconic Local Eats

Join a local guide for the ultimate foodie adventure in Chicago’s historic Loop, tasting classics like deep‑dish pizza and Chicago‑style hot dogs while discovering insider …More

4.9 (130)

Chicago Loop Food Tour: Taste the Most Iconic Local Eats

Join a local guide for the ultimate foodie adventure in Chicago’s historic Loop, tasting classics like deep‑dish pizza and Chicago‑style hot dogs while discovering insider...

2 hours Free Cancellation

4.9 (130)

from
$81

360 CHICAGO Observation Deck & Hop-on Hop-off Sightseeing Tour

Explore Chicago at your own pace with a 48-hour hop-on hop-off bus tour, providing unlimited access to the city's iconic neighborhoods and landmarks. Relax on …More

4.5 (4)

360 CHICAGO Observation Deck & Hop-on Hop-off Sightseeing Tour

Explore Chicago at your own pace with a 48-hour hop-on hop-off bus tour, providing unlimited access to the city's iconic neighborhoods and landmarks. Relax on...

2 hours Free Cancellation

4.5 (4)

from
$84

Art Institute of Chicago Skip-the-Line Exclusive Guided Tour

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour …More

5.0 (362)

Art Institute of Chicago Skip-the-Line Exclusive Guided Tour

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour...

2 hours 30 minutes Free Cancellation

5.0 (362)

from
$84

Skip the Line Chicago Art Institute Tour Semi-Private 12ppl Max

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour …More

5.0 (255)

Skip the Line Chicago Art Institute Tour Semi-Private 12ppl Max

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour...

2 hours 30 minutes Free Cancellation

5.0 (255)

from
$84

Chicago Favorites Ultimate Food and Walking Tour

The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour. Stroll the …More

4.9 (2,394)

Chicago Favorites Ultimate Food and Walking Tour

The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour. Stroll the...

3 hours Free Cancellation

4.9 (2,394)

from
$85

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

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)

from
$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)

from
$85

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

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

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)

from
$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)

from
$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

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military …More

5.0 (39)

Chicago Shoreline Adventure Boat Tour

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military...

1 hour 30 minutes Free Cancellation

5.0 (39)

from
$90

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)

from
$91