Holidays in Chicago

Holidays in Chicago

2 travellers
exact duration

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241 € - 408 €408 € - 575 €575 € - 742 €742 € - 908 €908 €+ per night

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Most popular Chicago flight and hotel deals

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The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet-friendly
Air Conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
268 €
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.5 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air Conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
336 €
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.3 Very Good
Loop
Free Wi-Fi
Pet-friendly
Air Conditioning
Fort Lauderdale
Meals not included
3 nights + flight
347 €
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
8.2 Very Good
O'Hare
Airport shuttle
Pool
Air Conditioning
Fort Lauderdale
Meals not included
3 nights + flight
426 €
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
8.9 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air Conditioning
Portland
Meals not included
3 nights + flight
649 €
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection
7.8 Good
Near North Side
Free Wi-Fi
Pet-friendly
Air Conditioning
Fort Lauderdale
Meals not included
3 nights + flight
310 €
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Air Conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
313 €
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bar
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bar
La Quinta Inn & Suites by Wyndham Chicago Downtown
8 Very Good
Loop
Free Wi-Fi
Pet-friendly
Air Conditioning
Fort Lauderdale
Breakfast
3 nights + flight
391 €
Waldorf Astoria Chicago - Chicago - Bar
Waldorf Astoria Chicago - Chicago - Bar
Waldorf Astoria Chicago
9.2 Wonderful
Near North Side
Pool
Pet-friendly
Air Conditioning
Los Angeles Los Angeles
Meals not included
3 nights + flight
712 €
The Langham Chicago - Chicago - Lounge
The Langham Chicago - Chicago - Lounge
The Langham Chicago
9.4 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air Conditioning
Portland
Meals not included
3 nights + flight
857 €
The Drake - Chicago - Lobby
The Drake - Chicago - Lobby
The Drake
8.3 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Air Conditioning
Fort Lauderdale
Meals not included
3 nights + flight
411 €
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago - Chicago - Bar
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago - Chicago - Bar
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
9 Wonderful
Near North Side
Pet-friendly
Air Conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
764 €
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.8 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air Conditioning
San Francisco
Meals not included
3 nights + flight
814 €
Club Quarters Hotel Wacker at Michigan, Chicago - Chicago - Building
Club Quarters Hotel Wacker at Michigan, Chicago - Chicago - Building
Club Quarters Hotel Wacker at Michigan, Chicago
8.3 Very Good
Loop
Free Wi-Fi
Pet-friendly
Air Conditioning
Fort Lauderdale
Meals not included
3 nights + flight
337 €
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection
8.3 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Air Conditioning
Fort Lauderdale
Meals not included
3 nights + flight
444 €
Club Quarters Hotel Central Loop, Chicago - Chicago - Lobby
Club Quarters Hotel Central Loop, Chicago - Chicago - Lobby
Club Quarters Hotel Central Loop, Chicago
8.2 Very Good
Loop
Free Wi-Fi
Pet-friendly
Air Conditioning
Fort Lauderdale
Meals not included
3 nights + flight
386 €

All inclusive holiday packages to Chicago

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The Wheeler Mansion - Chicago - Dining room
The Wheeler Mansion - Chicago - Dining room
The Wheeler Mansion
9.8 Wonderful
Near South Side
Free Wi-Fi
Air Conditioning
Boston Logan Intl
All-inclusive
3 nights + flight
725 €

Last minute holiday packages to Chicago

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Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94
2.6 Poor
Chatham
Parking
Pet-friendly
Air Conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
422 €
Chicago Avenue Inn - Chicago - Bathroom
Chicago Avenue Inn - Chicago - Bathroom
Chicago Avenue Inn
5.7 Fair
Humboldt Park
Parking
Free Wi-Fi
Air Conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
546 €
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.3 Wonderful
Near West Side
Pool
Pet-friendly
Air Conditioning
Dallas/Fort Worth
Breakfast
3 nights + flight
888 €
Wrigleyville Suites - Chicago - Living room
Wrigleyville Suites - Chicago - Living room
Wrigleyville Suites
7.8 Good
Wrigleyville
Free Wi-Fi
Air Conditioning
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
795 €

When to book a holiday in Chicago

Price includes flights and 3 nights accommodation for 2 travellers. Prices are not fixed and may vary with time.

Tips for finding cheap holiday packages Chicago

  • There are loads of types of holidays in Chicago and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travellers: Top holiday 30 €; Family holiday 120 €; Romantic holiday 120 €; Luxury holiday 677 €; Budget holiday 167 €.

Where to stay in Chicago

Our map will help you find the perfect place to stay for your holiday in Chicago by showing you the exact location of each hotel.

Everything you need to know for your holiday in Chicago

Chicago holiday information

Top holiday (Flight+Hotel)30 €
Family holiday (Flight+Hotel)120 €
Romantic holiday (Flight+Hotel)120 €
Luxury holiday (Flight+Hotel)677 €
Budget holiday (Flight+Hotel)167 €