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
Boston Logan Intl
Meals not included
3 nights + flight
C$ 524
Near North Side
Free Wi-Fi
Pool
Pet friendly
Burbank Bob Hope
Meals not included
3 nights + flight
C$ 473
Near North Side
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 604
Near North Side
Free Wi-Fi
Pet friendly
Boston Logan Intl
Breakfast
3 nights + flight
C$ 520
Downtown
Pet friendly
Newark
Breakfast
3 nights + flight
C$ 542
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
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
C$ 556
The 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
Boston Logan Intl
Meals not included
3 nights + flight
C$ 580
Near West Side
Free Wi-Fi
Newark
Meals not included
3 nights + flight
C$ 595
The St. Regis Chicago - Chicago - Restaurant![The St. Regis Chicago - Chicago - Restaurant]()
The St. Regis Chicago
Downtown
Pool
Pet friendly
Spa
Portland
Meals not included
3 nights + flight
C$ 1,349
Downtown
Pet friendly
Spa
Burbank Bob Hope
Meals not included
3 nights + flight
C$ 507
The Neighborhood Hotel Little Italy - Chicago - Living room![The Neighborhood Hotel Little Italy - Chicago - Living room]()
The Neighborhood Hotel Little Italy
Near West Side
Minneapolis St Paul
Meals not included
3 nights + flight
C$ 691
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
Burbank Bob Hope
Meals not included
3 nights + flight
C$ 460
Downtown
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
C$ 568
Near North Side
Free Wi-Fi
Pool
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
C$ 565
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
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
C$ 570
Near North Side
Free Wi-Fi
Dallas/Fort Worth
Breakfast
3 nights + flight
C$ 577
Last minute vacation packages to Chicago
Show allHyatt 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
Memphis
Breakfast
3 nights + flight
C$ 695
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$ 724; Family vacation C$ 657; Romantic vacation C$ 765; Luxury vacation C$ 758; Budget vacation C$ 540.
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$ 724 |
|---|---|
| Family vacation (Flight+Hotel) | C$ 657 |
| Romantic vacation (Flight+Hotel) | C$ 765 |
| Luxury vacation (Flight+Hotel) | C$ 758 |
| Budget vacation (Flight+Hotel) | C$ 540 |