Holidays in Chicago
2 travellers
Exact dates
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Most popular Chicago flight and hotel deals
Show allNear North Side
Free Wi-Fi
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€327
Sonder Onterie - Chicago - Living room![Sonder Onterie - Chicago - Living room]()
Sonder Onterie
Near North Side
Free Wi-Fi
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€399
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Newark
Meals not included
3 nights + flight
€245
Near North Side
Free Wi-Fi
Air conditioning
Newark
Breakfast
3 nights + flight
€291
Hyatt House Chicago Medical/University District - Chicago - Building![Hyatt House Chicago Medical/University District - Chicago - Building]()
Hyatt House Chicago Medical/University District
Near West Side
Free Wi-Fi
Pet friendly
Air conditioning
Los Angeles
Breakfast
3 nights + flight
€321
O'Hare
Airport shuttle
Pool
Air conditioning
Owensboro Daviess County
Meals not included
3 nights + flight
€280
Downtown
Pet friendly
Air conditioning
Los Angeles
Breakfast
3 nights + flight
€342
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Houston George Bush Intcntl
Meals not included
3 nights + flight
€343
Hampton Inn & Suites Chicago Medical District UIC - Chicago - Bedroom![Hampton Inn & Suites Chicago Medical District UIC - Chicago - Bedroom]()
Hampton Inn & Suites Chicago Medical District UIC
Near West Side
Pool
Pet friendly
Air conditioning
Newark
Breakfast
3 nights + flight
€324
The St. Regis Chicago - Chicago - Restaurant![The St. Regis Chicago - Chicago - Restaurant]()
The St. Regis Chicago
Downtown
Pool
Pet friendly
Air conditioning
Hartford Bradley Intl
Meals not included
3 nights + flight
€1,062
Downtown
Free Wi-Fi
Pet friendly
Air conditioning
Orlando
Meals not included
3 nights + flight
€340
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
Orlando
Meals not included
3 nights + flight
€449
Downtown
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Houston George Bush Intcntl
Meals not included
3 nights + flight
€360
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
Orlando
Meals not included
3 nights + flight
€341
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Houston George Bush Intcntl
Meals not included
3 nights + flight
€584
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Newark
Breakfast
3 nights + flight
€287
Last minute holiday packages to Chicago
Show allThe Royal Sonesta Chicago River North - Chicago - Lounge![The Royal Sonesta Chicago River North - Chicago - Lounge]()
The Royal Sonesta Chicago River North
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Houston George Bush Intcntl
Meals not included
3 nights + flight
€389
Near North Side
Free Wi-Fi
Pool
Air conditioning
Houston George Bush Intcntl
Meals not included
3 nights + flight
€308
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 €1,232; Romantic holiday €1,296; Luxury holiday €1,306; Budget holiday €1,062.
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
Complete your trip to Chicago
Chicago holiday information
| Family holiday (Flight+Hotel) | €1,232 |
|---|---|
| Romantic holiday (Flight+Hotel) | €1,296 |
| Luxury holiday (Flight+Hotel) | €1,306 |
| Budget holiday (Flight+Hotel) | €1,062 |