Holidays in Chicago
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Cheap Chicago package deals
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Most popular Chicago flight and hotel deals
Show allFlexible Room Choices & Modern Amenities ! - Chicago![Flexible Room Choices & Modern Amenities ! - Chicago]()
Flexible Room Choices & Modern Amenities !
Near West Side
Parking
Free Wi-Fi
Air conditioning
New York LaGuardia
Meals not included
3 nights + flight
€397
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Building![Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Building]()
Residence Inn by Marriott Chicago Downtown Magnificent Mile
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Cleveland Hopkins Intl
Breakfast
3 nights + flight
€369
Hyatt House Chicago Medical/University District - Chicago - Bedroom![Hyatt House Chicago Medical/University District - Chicago - Bedroom]()
Hyatt House Chicago Medical/University District
Near West Side
Free Wi-Fi
Pet friendly
Air conditioning
Los Angeles
Breakfast
3 nights + flight
€216
O'Hare
Airport shuttle
Pool
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€240
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€251
Downtown
Free Wi-Fi
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€151
South Side
Free Wi-Fi
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€167
Downtown
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
€274
The St. Regis Chicago - Chicago - Bedroom![The St. Regis Chicago - Chicago - Bedroom]()
The St. Regis Chicago
Downtown
Pool
Pet friendly
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
€622
Downtown
Free Wi-Fi
Pet friendly
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€232
Homewood Suites by Hilton - Chicago Downtown South Loop - Chicago - Living room![Homewood Suites by Hilton - Chicago Downtown South Loop - Chicago - Living room]()
Homewood Suites by Hilton - Chicago Downtown South Loop
Downtown
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Houston George Bush Intcntl
Breakfast
3 nights + flight
€247
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room![The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room]()
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown
Pet friendly
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€238
Chicago Avenue Inn - Chicago - Living room![Chicago Avenue Inn - Chicago - Living room]()
Chicago Avenue Inn
Humboldt Park
Parking
Free Wi-Fi
Air conditioning
Denver Intl
Meals not included
3 nights + flight
€167
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby![SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby]()
SpringHill Suites by Marriott Chicago Chinatown
South Side
Free Wi-Fi
Air conditioning
Washington, D.C. Reagan-National
Breakfast
3 nights + flight
€375
Riu Plaza Chicago - Chicago - Lounge![Riu Plaza Chicago - Chicago - Lounge]()
Riu Plaza Chicago
Near North Side
Free Wi-Fi
Air conditioning
Dallas/Fort Worth
Breakfast
3 nights + flight
€281
Spacious Shared Condo Near Downtown Chicago, Flexible Room Choices and Shared Amenities - Chicago![Spacious Shared Condo Near Downtown Chicago, Flexible Room Choices and Shared Amenities - Chicago]()
Spacious Shared Condo Near Downtown Chicago, Flexible Room Choices and Shared Amenities
Near West Side
Parking
Free Wi-Fi
Air conditioning
Dallas/Fort Worth
Meals not included
3 nights + flight
€158
Last minute holiday packages to Chicago
Show allThe 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
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€304
Sonder The Burnham - Chicago - Living room![Sonder The Burnham - Chicago - Living room]()
Sonder The Burnham
Near West Side
Free Wi-Fi
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€315
Near North Side
Free Wi-Fi
Pool
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€311
Lincoln Park
Free Wi-Fi
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€205
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 Chicago package deals
- 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: Family holiday €1,312; Romantic holiday €1,380; Luxury holiday €1,391; Budget holiday €1,131.
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.
Chicago holiday information
| Family holiday (Flight+Hotel) | €1,312 |
|---|---|
| Romantic holiday (Flight+Hotel) | €1,380 |
| Luxury holiday (Flight+Hotel) | €1,391 |
| Budget holiday (Flight+Hotel) | €1,131 |
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