Vacations in Chicago
2 travellers
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Most popular Chicago flight and hotel deals
Show allNear North Side
Free Wi-Fi
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 522
Near North Side
Free Wi-Fi
Pool
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 498
Near North Side
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 683
Near North Side
Free Wi-Fi
Pool
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 349
Near North Side
Free Wi-Fi
Washington, D.C. Dulles Intl
Breakfast
3 nights + flight
C$ 481
Near North Side
Free Wi-Fi
Pet friendly
Los Angeles
Breakfast
3 nights + flight
C$ 524
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
San Francisco
Meals not included
3 nights + flight
C$ 930
The St. Regis Chicago - Chicago - Restaurant![The St. Regis Chicago - Chicago - Restaurant]()
The St. Regis Chicago
Downtown
Pool
Pet friendly
Spa
Santa Ana J. Wayne/Orange Cnty
Meals not included
3 nights + flight
C$ 1,244
The Neighborhood Hotel Little Italy - Chicago - Living room![The Neighborhood Hotel Little Italy - Chicago - Living room]()
The Neighborhood Hotel Little Italy
Near West Side
Philadelphia
Meals not included
3 nights + flight
C$ 685
Downtown
Free Wi-Fi
Pool
Pet friendly
Washington, D.C. Dulles Intl
Meals not included
3 nights + flight
C$ 581
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
Los Angeles
Meals not included
3 nights + flight
C$ 520
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Philadelphia
Meals not included
3 nights + flight
C$ 533
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
Detroit Metropolitan Wayne County
Breakfast
3 nights + flight
C$ 603
Near North Side
Free Wi-Fi
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 643
Last minute vacation 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
Philadelphia
Meals not included
3 nights + flight
C$ 1,067
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
Philadelphia
Breakfast
3 nights + flight
C$ 966
When to book a vacation 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 vacations 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 vacation C$ 721; Family vacation C$ 653; Romantic vacation C$ 761; Luxury vacation C$ 754; Budget vacation C$ 537.
Where to stay in Chicago
Our map will help you find the perfect place to stay for your vacation in Chicago by showing you the exact location of each hotel.
Everything you need to know for your vacation in Chicago
Complete your trip to Chicago
Chicago vacation information
| Top vacation (Flight+Hotel) | C$ 721 |
|---|---|
| Family vacation (Flight+Hotel) | C$ 653 |
| Romantic vacation (Flight+Hotel) | C$ 761 |
| Luxury vacation (Flight+Hotel) | C$ 754 |
| Budget vacation (Flight+Hotel) | C$ 537 |