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United States · luxury

Luxury Travel in Chicago

Lakefront runs, deep-dish lunches, river architecture cruises at golden hour. The high-end side of Chicago — private guides, VIP access and premium experiences worth the splurge, all bookable in advance.

Chicago travel guide →3-day plan →Weekend in Chicago →

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Top experiences in Chicago

Bookable through GetYourGuide. Skip-the-line, verified guides.

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1h to 1h 30m

Chicago Architecture River Cruise

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River.

  • Top-rated · 4.8★
  • Bestseller
From $39 a person
This tour cruises the Chicago River and Lake Michigan.
1h 30m

Chicago Lake and River Architecture Tour

An authentic Chicago tradition since 1935, this is the tour that started it all.

  • 4.7★ · 2360 reviews
  • Bestseller
From $45 a person
1h 30m

Chicago Architecture Center River Cruise aboard First Lady

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture...

  • Top-rated · 4.9★
  • Bestseller
From $57 a person
See Chicago's magnificent skyline at night!
1h 30m

Chicago By Night River and Lake Cruise

Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night!

  • Free cancellation
  • Instant confirmation
From $50 a person
2h

Luxury Minibus Chicago City Tour

Experience Chicago in Style with Our Luxury City Sightseeing Minibus Tour.

  • Free cancellation
  • Instant confirmation
From $65 a person
2h

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Sail along the magnificent skyline on our Premier Plus Chicago Brunch Cruise.

  • Free cancellation
  • Instant confirmation
From $85 a person
216h

Chicago CityPASS®

Experience 5 top attractions and save up to 50% with Chicago CityPASS® tickets.

  • Instant confirmation
From $144 a person
1h

Private Arrival Transfer from Chicago Airports (ORD) (MDW)

Why stress about finding a taxi at Chicago's busy airports when you can book a private car in advance?

  • Free cancellation
  • Instant confirmation
From $90 a person
Taste deep-dish pizza, a Chicago-style hot dog, Italian beef, Garrett’s popcorn & the original 1893 brownie on our top-rated Chicago Food Tours—the ultimate Chicago Culinary Tour experience!
3h

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.

  • Top-rated · 4.8★
  • Bestseller
From $85 a person
1h 30m

Chicago Fireboat Fireworks Cruise

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise.

  • Free cancellation
  • Instant confirmation
From $57 a person
1h 30m

Chicago True Crime and Gangsters Tour

Our goal is to disturb and unsettle you of whatever assumptions you may have about Chicago.

  • Free cancellation
  • Instant confirmation
From $35 a person
30 min to 45 min

Lake Michigan Skyline Cruise in Chicago

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions.

  • Free cancellation
  • Instant confirmation
From $33 a person
2h

Chicago Walking Tour: Historic Treasures of Chicago

Learn about the great architectural landmarks of Michigan Avenue and State Street.

  • Top-rated · 4.9★
  • Free cancellation
From $35 a person
Daley Plaza Picasso
1h 30m

Chicago Walking Tour: Must-See Chicago

Must-See Chicago is a fast-paced, 90-minute introductory tour to Chicago featuring some of its most famous buildings, including the Wrigley Building, Tribune Tower, the Art...

  • Top-rated · 4.9★
  • Free cancellation
From $35 a person
2h

Chicago Private Night Skyline and Lakefront Scenic Tour

Experience Chicago’s glowing skyline and scenic lakefront on a private, fully personalized night tour.

  • Free cancellation
  • Instant confirmation
From $113 a person
2h 30m

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

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

  • Top-rated · 5.0★
  • Free cancellation
From $90 a person
3h

Skyline, Lakefront and Millennium Park Chicago Private Day Tour

Explore Chicago’s iconic landmarks and scenic lakefront on a private, fully personalized city tour.

  • Free cancellation
  • Instant confirmation
From $168 a person
2h to 8h

Chicago City Private Tours

Ready to explore Chicago like never before?

  • Free cancellation
  • Instant confirmation
From $199 a person
1 to 1.5 hrs

Chicago 4-Hour Sightseeing Transfer by Luxury Private Sedan

Safe & sanitized vehicles.

  • Free cancellation
  • Private tour
From $190 a person
30 min

Private Luxury day Transfer from Linate Airport to Milan

Secure a comfortable and convenient private transfer from Linate Airports to your accommodation in Milano city center.

  • 4.7★ · 54 reviews
  • Free cancellation
From $40 a person
Cultural Centers Tiffany Dome
1h 30m to 1h 45m

Chicago Architecture and True Crime History Tour

Get the best of both worlds: explore Chicago’s stunning architecture while uncovering its dark past.

  • Top-rated · 5.0★
  • Free cancellation
From $35 a person
Budapest
4h

Budapest Highlights & Hidden Gems – Private Luxury Experience

This is not a standard sightseeing tour – it is a fully private, tailor-made experience designed around you.

  • Top-rated · 4.9★
  • Free cancellation
From $469 a person
Front of Museum
2h

Private Chicago History Museum Tour

Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life through captivating...

  • Free cancellation
  • Instant confirmation
From $163 a person
2h

Original Chicago Architecture Interiors Tour: Dazzling Interiors

UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper!

  • Top-rated · 5.0★
  • Bestseller
From $35 a person

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