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Chicago Offers 10
Chicago Hotels 54
USA Fly-Drives 32
Chicago Offers 10
Chicago Hotels 54
Chicago Fly-Drives 3
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Illinois Iconic Route 66 - Fly Drive

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8 nts / 9 days from £1,279pp
Includes flights and car hire
Illinois Iconic Route 66 - Fly Drive
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Sable at Navy Pier 4*

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3 nights from £1,099pp
Includes flights
Sable at Navy Pier 4*
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Rhythms of the River - Fly Drive

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10 nts / 11 days from £1,719pp
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Rhythms of the River - Fly Drive
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The Drake 4*

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3 nights from £999pp
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The Drake 4*
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Palmer House Hilton 5*

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3 nights from £799pp
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Palmer House Hilton 5*
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Ambassador Hotel 5*

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3 nights from £719pp
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Ambassador Hotel 5*
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Silversmith Hotel 4*

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3 nights from £889pp
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Silversmith Hotel 4*
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Fairmont Chicago, Millennium Park 5*

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3 nights from £1,049pp
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Fairmont Chicago, Millennium Park 5*
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Cruise Route 66 - Fly Drive

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15 nts / 16 days from £2,139pp
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Cruise Route 66 - Fly Drive
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The Millennium Knickerbocker 4*

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3 nights from £985pp
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The Millennium Knickerbocker 4*
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Chicago Offers 10
Chicago Hotels 54
USA Fly-Drives 32

The Peninsula Chicago

The
★ ★ ★ ★ ★
Fr £512 per room night

Set in the heart of Chicago, on the city’s Magnificent Mile, known for its excellent shopping and...

Four Seasons Hotel Chicago

Four
★ ★ ★ ★ ★
Fr £422 per room night

In a location just minutes from the city’s business and financial districts, the Four Seasons...

Waldorf Astoria Chicago

Waldorf
★ ★ ★ ★ ★
Fr £330 per room night

Experience Parisian-style charm near Michigan Avenue at our Downtown Chicago's Gold Coast...

The Ritz-Carlton Chicago

The
★ ★ ★ ★ ★
Fr £328 per room night

Enjoy world-class Michigan Avenue shopping, unrivalled cuisine and rich cultural offerings, all...

Sofitel Chicago Magnificent Mile

Sofitel
★ ★ ★ ★ ★
Fr £214 per room night

Centrally located in Chicago's downtown, just minutes from Magnificent Mile, the luxurious Sofitel...

Swissôtel Chicago

Swissôtel
★ ★ ★ ★ ★
Fr £173 per room night

Set in a stunning all-glass triangular building at the heart of downtown Chicago, just steps from...

Fairmont Chicago - Millennium Park

Fairmont
★ ★ ★ ★ ★
Fr £166 per room night

The Fairmont Chicago, Millennium Park is a sophisticated, modern hotel set in the heart of downtown...

Save 10% (inc flights)

Club Quarters Hotel Chicago Central Loop

Club
★ ★ ★ ★ ★
Fr £119 per room night

Take advantage of recreation opportunities such as a 24-hour fitness center, or other amenities...

The Drake Hotel

The
★ ★ ★ ★ ★
Fr £114 per room night

Situated at the top of the Magnificent Mile, The Drake is a Chicago icon which seamlessly blends...

Ambassador Chicago

Ambassador
★ ★ ★ ★ ★
Fr £100 per room night

Set in Chicago’s central Gold Coast neighbourhood, the Ambassador Chicago is a historic boutique...

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