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: Lincoln Park Secrets: Private Enchanted Pedicab History Tour Private Christmas Walking Tour in Chicago with Christkindlmarket Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit Wicker Park Walking Tour History Trivia and Local Flavors Chicago River Fireworks 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 →

Discover iconic Chicago movie locations with a private tour, including transportation and hotel pickup and drop-off. Visit the Home Alone house exterior, Wrigley Field exterior …More

5.0 (11)

Chicago Movie Locations Tour

Discover iconic Chicago movie locations with a private tour, including transportation and hotel pickup and drop-off. Visit the Home Alone house exterior, Wrigley Field exterior...

3 hours Hotel pickup offered Free Cancellation

5.0 (11)

from
$315

Experience the ultimate Private Shameless TV Location Tour with the convenience of hotel pick and drop-off, allowing you to sit back, relax and enjoy the …More

5.0 (5)

Shameless TV Show Location Tour

Experience the ultimate Private Shameless TV Location Tour with the convenience of hotel pick and drop-off, allowing you to sit back, relax and enjoy the...

2 hours Hotel pickup offered Free Cancellation

5.0 (5)

from
$315

One Day Galena and Dubuque Tour from Chicago

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque, …More

3.0 (2)

One Day Galena and Dubuque Tour from Chicago

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque,...

9 to 10 hours Hotel pickup offered Free Cancellation

3.0 (2)

from
$315

Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods …More

5.0 (1)

Chicago Small Group City Tour

Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods...

9 to 10 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$340

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

Chicago Helicopter Tour: City to Shoreline

Your journey begins with a southeast departure from the Vertiport, offering early views of the city’s iconic skyline. Flying east, you’ll head toward the lakefront …More

4.4 (33)

Chicago Helicopter Tour: City to Shoreline

Your journey begins with a southeast departure from the Vertiport, offering early views of the city’s iconic skyline. Flying east, you’ll head toward the lakefront...

20 to 25 minutes Free Cancellation

4.4 (33)

from
$350

Experience the best of the Chicagoland area in style and comfort with our exclusive SUV tours. Discover the city's iconic landmarks, including the breathtaking parks, …More

4.5 (2)

Luxury SUV 4 Hour Sightseeing Tour

Experience the best of the Chicagoland area in style and comfort with our exclusive SUV tours. Discover the city's iconic landmarks, including the breathtaking parks,...

2 to 4 hours Hotel pickup offered Free Cancellation

4.5 (2)

from
$350

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to …More

Private Tour Art Institute of Chicago Guided Museum

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to...

5 hours Hotel pickup offered

from
$439

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

Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal …More

5.0 (3)

Private Holiday City Tour

Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal...

3 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$499

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed …More

5.0 (71)

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed...

2 hours Free Cancellation

5.0 (71)

from
$508

Chicago Private Custom City Tour with Hotel Pick Up

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS. Thank you for contacting Chicago Private Tours! We would love to help your …More

5.0 (203)

Chicago Private Custom City Tour with Hotel Pick Up

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS. Thank you for contacting Chicago Private Tours! We would love to help your...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (203)

from
$539

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city …More

4 Hours of Chicago City Tour Sedan

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city...

4 hours Hotel pickup offered Free Cancellation

from
$640

Experience the best of Chicago on this private full-day city tour designed for a fun, stress-free day of exploring. Enjoy comfortable hotel pickup, ride in …More

Private and All-Inclusive Tour of Chicago

Experience the best of Chicago on this private full-day city tour designed for a fun, stress-free day of exploring. Enjoy comfortable hotel pickup, ride in...

6 hours Hotel pickup offered Free Cancellation

from
$750

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 10 PASSENGERS TOTAL. Thank you for contacting Chicago Private Tours! We would love to help …More

5.0 (3)

Private City Tour 6-10ppl

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 10 PASSENGERS TOTAL. Thank you for contacting Chicago Private Tours! We would love to help...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (3)

from
$770

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city …More

5.0 (2)

4-Hour Chicago City Tour by SUV

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city...

4 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$800

Private 45-Minute Chicago Skyline Helicopter Tour

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience …More

4.9 (126)

Private 45-Minute Chicago Skyline Helicopter Tour

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience...

45 minutes Free Cancellation

4.9 (126)

from
$849

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city …More

5.0 (1)

Chicago 6-Hour City Tour by Sedan

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city...

6 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$960

Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

Take in three of the Great Lakes and a string of classic Midwest towns on this four-day small-group loop out of Chicago. Travel up the …More

5.0 (3)

Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

Take in three of the Great Lakes and a string of classic Midwest towns on this four-day small-group loop out of Chicago. Travel up the...

4 days Free Cancellation

5.0 (3)

from
$995

Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on …More

5.0 (1)

Private Chicago City Minibus Tour

Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on...

2 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$999