Vacations in Chicago

Vacations in Chicago

2 travellers

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Cheap Chicago package deals

These are the best prices for Apr 24 - 27.
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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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C$ 291 - C$ 447C$ 447 - C$ 603C$ 603 - C$ 760C$ 760 - C$ 916C$ 916+ per night

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Most popular Chicago flight and hotel deals

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Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lounge
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lounge
Residence Inn by Marriott Chicago Downtown Magnificent Mile
9 Wonderful
Near North Side
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Breakfast
3 nights + flight
C$ 492
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG
8.2 Very good
Near West Side
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 408
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
8.1 Very good
O'Hare
Airport shuttle
Pool
Miami
Meals not included
3 nights + flight
C$ 454
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 412
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 638
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.3 Wonderful
Near West Side
Pool
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 478
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
8.6 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 419
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop
8.9 Very good
Downtown
Free Wi-Fi
Pet friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 424
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 386
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop
8.9 Very good
Downtown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Breakfast
3 nights + flight
C$ 482
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago
9.2 Wonderful
Near North Side
Pool
Pet friendly
Spa
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 997
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.2 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 579
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk
8.4 Very good
Downtown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 413
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.6 Very good
Downtown
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 466
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago
8.6 Very good
Downtown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 467
Freehand Chicago - Chicago - Lounge
Freehand Chicago - Chicago - Lounge
Freehand Chicago
7.2 Good
Near North Side
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 363

All inclusive vacation packages to Chicago

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The Wheeler Mansion - Chicago - Dining room
The Wheeler Mansion - Chicago - Dining room
The Wheeler Mansion
9.8 Wonderful
Near South Side
Free Wi-Fi
Atlanta Hartsfield-Jackson
All inclusive
3 nights + flight
C$ 1,421

Last minute vacation packages to Chicago

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The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy
Near West Side
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 810
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.3 Very good
Near North Side
Free Wi-Fi
Pool
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 384
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.7 Very good
Near West Side
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Breakfast
3 nights + flight
C$ 462

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$ 95; Family vacation C$ 269; Romantic vacation C$ 242; Luxury vacation C$ 507; Budget vacation C$ 261.

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

Chicago vacation information

Top vacation (Flight+Hotel)C$ 95
Family vacation (Flight+Hotel)C$ 269
Romantic vacation (Flight+Hotel)C$ 242
Luxury vacation (Flight+Hotel)C$ 507
Budget vacation (Flight+Hotel)C$ 261