Vacations in Chicago
2 travellers
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Cheap Chicago package deals
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Most popular Chicago flight and hotel deals
Show allSonder Onterie - Chicago - Living room![Sonder Onterie - Chicago - Living room]()
Sonder Onterie
Near North Side
Free Wi-Fi
Minneapolis St Paul
Meals not included
3 nights + flight
C$ 556
Near North Side
Free Wi-Fi
Pool
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
C$ 390
Near North Side
Free Wi-Fi
Nashville Intl
Meals not included
3 nights + flight
C$ 478
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
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 597
Downtown
Pet friendly
Nashville Intl
Breakfast
3 nights + flight
C$ 518
Near North Side
Free Wi-Fi
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
C$ 501
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
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 590
The St. Regis Chicago - Chicago - Restaurant![The St. Regis Chicago - Chicago - Restaurant]()
The St. Regis Chicago
Downtown
Pool
Pet friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 1,284
The Neighborhood Hotel Little Italy - Chicago - Living room![The Neighborhood Hotel Little Italy - Chicago - Living room]()
The Neighborhood Hotel Little Italy
Near West Side
Nashville Intl
Meals not included
3 nights + flight
C$ 631
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
Nashville Intl
Meals not included
3 nights + flight
C$ 468
Sonder The Burnham - Chicago - Living room![Sonder The Burnham - Chicago - Living room]()
Sonder The Burnham
Near West Side
Free Wi-Fi
Minneapolis St Paul
Meals not included
3 nights + flight
C$ 555
Downtown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 552
Chicago Avenue Inn - Chicago - Dining room![Chicago Avenue Inn - Chicago - Dining room]()
Chicago Avenue Inn
Humboldt Park
Parking
Free Wi-Fi
Newark
Meals not included
3 nights + flight
C$ 320
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
Houston George Bush Intcntl
Breakfast
3 nights + flight
C$ 560
Last minute vacation packages to Chicago
Show allNear North Side
Free Wi-Fi
Pool
Tulsa
Meals not included
3 nights + flight
C$ 1,555
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$ 732; Family vacation C$ 664; Romantic vacation C$ 774; Luxury vacation C$ 766; Budget vacation C$ 546.
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$ 732 |
|---|---|
| Family vacation (Flight+Hotel) | C$ 664 |
| Romantic vacation (Flight+Hotel) | C$ 774 |
| Luxury vacation (Flight+Hotel) | C$ 766 |
| Budget vacation (Flight+Hotel) | C$ 546 |