Vacations in Chicago

Vacations in Chicago

2 travellers
Tue 4/2
Fri 4/5

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Cheap Chicago package deals

Most popular Chicago flight and hotel deals

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Rodeway Inn
6.3 Okay
West Ridge
Parking
Free Wi-Fi
Seattle/Tacoma Intl
Meals not included
3 nights + flight
C$ 261
Downtown
Pet friendly
Spa
Seattle/Tacoma Intl
Meals not included
3 nights + flight
C$ 460
O'Hare
Airport shuttle
Pool
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 378
Downtown
Free Wi-Fi
Pet friendly
Seattle/Tacoma Intl
Breakfast
3 nights + flight
C$ 425
Archer Heights
Parking
Airport shuttle
Free Wi-Fi
Pet friendly
New York LaGuardia
Breakfast
3 nights + flight
C$ 319
Park Hyatt Chicago
8.9 Very good
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Philadelphia
Meals not included
3 nights + flight
C$ 701
Downtown
Pet friendly
Charlotte Douglas
Meals not included
3 nights + flight
C$ 376
Downtown
Free Wi-Fi
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 282
Downtown
Pet friendly
Raleigh-Durham
Meals not included
3 nights + flight
C$ 407
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Portland
Meals not included
3 nights + flight
C$ 739
Downtown
Free Wi-Fi
Pool
Pet friendly
Seattle/Tacoma Intl
Meals not included
3 nights + flight
C$ 455
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown
9.1 Wonderful
Downtown
Free Wi-Fi
Portland
Breakfast
3 nights + flight
C$ 445
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 881
Downtown
Free Wi-Fi
Charlotte Douglas
Meals not included
3 nights + flight
C$ 266
The Talbott Hotel
8.2 Very good
Downtown
Free Wi-Fi
Pet friendly
Seattle/Tacoma Intl
Meals not included
3 nights + flight
C$ 355

Last minute vacation packages to Chicago

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The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
8.3 Very good
Downtown
Free Wi-Fi
Pool
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
C$ 492
Downtown
Free Wi-Fi
Pool
Minneapolis St Paul
Meals not included
3 nights + flight
C$ 499

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$ 717; Family vacation C$ 650; Romantic vacation C$ 758; Luxury vacation C$ 751; Budget vacation C$ 535.

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.

Chicago vacation information

Top vacation (Flight+Hotel)C$ 717
Family vacation (Flight+Hotel)C$ 650
Romantic vacation (Flight+Hotel)C$ 758
Luxury vacation (Flight+Hotel)C$ 751
Budget vacation (Flight+Hotel)C$ 535