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
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 620
Near North Side
Free Wi-Fi
Pool
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 417
Near North Side
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
C$ 567
Near West Side
Free Wi-Fi
Pet friendly
Nashville Intl
Breakfast
3 nights + flight
C$ 497
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
Meals not included
3 nights + flight
C$ 627
Downtown
Pet friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
C$ 536
Near North Side
Free Wi-Fi
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
C$ 599
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
Nashville Intl
Meals not included
3 nights + flight
C$ 550
Downtown
Free Wi-Fi
Pet friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 496
The Neighborhood Hotel Little Italy - Chicago - Living room![The Neighborhood Hotel Little Italy - Chicago - Living room]()
The Neighborhood Hotel Little Italy
Near West Side
Baltimore/Washington
Meals not included
3 nights + flight
C$ 669
Near North Side
Free Wi-Fi
Nashville Intl
Meals not included
3 nights + flight
C$ 662
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Los Angeles
Meals not included
3 nights + flight
C$ 1,017
Near North Side
Free Wi-Fi
Pool
Nashville Intl
Meals not included
3 nights + flight
C$ 471
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Los Angeles
Meals not included
3 nights + flight
C$ 532
Chicago Avenue Inn - Chicago - Dining room![Chicago Avenue Inn - Chicago - Dining room]()
Chicago Avenue Inn
Humboldt Park
Parking
Free Wi-Fi
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 394
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Charlotte Douglas
Meals not included
3 nights + flight
C$ 1,331
Last minute vacation packages to Chicago
Show allSonder The Burnham - Chicago - Living room![Sonder The Burnham - Chicago - Living room]()
Sonder The Burnham
Near West Side
Free Wi-Fi
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 701
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$ 733; Family vacation C$ 665; Romantic vacation C$ 775; Luxury vacation C$ 767; Budget vacation C$ 547.
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$ 733 |
|---|---|
| Family vacation (Flight+Hotel) | C$ 665 |
| Romantic vacation (Flight+Hotel) | C$ 775 |
| Luxury vacation (Flight+Hotel) | C$ 767 |
| Budget vacation (Flight+Hotel) | C$ 547 |