Holidays in Chicago

Holidays in Chicago

2 travellers
exact duration

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194 € - 382 €382 € - 570 €570 € - 757 €757 € - 945 €945 €+ 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
7.8 Good
Near North Side
Pool
Pet-friendly
Air Conditioning
Baltimore/Washington
Meals not included
3 nights + flight
317 €
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG
8 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air Conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
460 €
Mccormick Place Guest House - Chicago - Balcony
Mccormick Place Guest House - Chicago - Balcony
Mccormick Place Guest House
5.8 Fair
Douglas
Parking
Free Wi-Fi
Air Conditioning
Baltimore/Washington
Meals not included
3 nights + flight
308 €
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
Baltimore/Washington
Meals not included
3 nights + flight
426 €
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG
8 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Air Conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
335 €
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
Nashville Intl
Meals not included
3 nights + flight
358 €
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air Conditioning
Austin Bergstrom
Meals not included
3 nights + flight
857 €
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
Minneapolis St Paul
Meals not included
3 nights + flight
235 €
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Air Conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
295 €
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.3 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air Conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
668 €
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.2 Very Good
Near North Side
Free Wi-Fi
Pool
Air Conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
420 €
The Drake - Chicago - Lobby
The Drake - Chicago - Lobby
The Drake
8.3 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Air Conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
333 €
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.9 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air Conditioning
Baltimore/Washington
Meals not included
3 nights + flight
864 €
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago
8.6 Very Good
Loop
Free Wi-Fi
Pet-friendly
Air Conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
496 €
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel
8.1 Very Good
Loop
Free Wi-Fi
Pet-friendly
Air Conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
244 €
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.1 Good
Loop
Free Wi-Fi
Air Conditioning
Minneapolis St Paul
Meals not included
3 nights + flight
298 €

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
Los Angeles
All-inclusive
3 nights + flight
753 €

Last minute holiday packages to Chicago

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The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
8.5 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Air Conditioning
Austin Bergstrom
Meals not included
3 nights + flight
497 €
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Air Conditioning
Newark
Meals not included
3 nights + flight
580 €
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.8 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Air Conditioning
Austin Bergstrom
Breakfast
3 nights + flight
483 €

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 119 €; Romantic holiday 119 €; Luxury holiday 672 €; Budget holiday 322 €.

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)119 €
Romantic holiday (Flight+Hotel)119 €
Luxury holiday (Flight+Hotel)672 €
Budget holiday (Flight+Hotel)322 €