Vacations in Chicago

Vacations in Chicago

2 travellers

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Cheap Chicago package deals

These are the best prices for Jun 15 - 18.
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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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C$ 313 - C$ 596C$ 596 - C$ 877C$ 877 - C$ 1,160C$ 1,160 - C$ 1,443C$ 1,443+ per night

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Free breakfastFree internetFree airport shuttleFree parking

Most popular Chicago flight and hotel deals

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The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet friendly
Newark
Meals not included
3 nights + flight
C$ 924
The Godfrey Hotel Chicago - Chicago - Lobby
The Godfrey Hotel Chicago - Chicago - Lobby
The Godfrey Hotel Chicago
8 Very good
Near North Side
Free Wi-Fi
Spa
Philadelphia
Meals not included
3 nights + flight
C$ 709
The Chicago Hotel Collection Ambassador Gold Coast - Chicago - Lounge
The Chicago Hotel Collection Ambassador Gold Coast - Chicago - Lounge
The Chicago Hotel Collection Ambassador Gold Coast
8.1 Very good
Near North Side
Newark
Meals not included
3 nights + flight
C$ 541
Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94
2.9 Poor
South Side
Parking
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
C$ 312
Hilton Chicago - Chicago - Living room
Hilton Chicago - Chicago - Living room
Hilton Chicago
7.9 Good
Downtown
Free Wi-Fi
Pool
Pet friendly
Columbus
Meals not included
3 nights + flight
C$ 731
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
7.9 Good
Near North Side
Pool
Pet friendly
Philadelphia
Breakfast
3 nights + flight
C$ 827
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
Columbus
Meals not included
3 nights + flight
C$ 579
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
Philadelphia
Meals not included
3 nights + flight
C$ 691
Palmer House a Hilton Hotel - Chicago - Lounge
Palmer House a Hilton Hotel - Chicago - Lounge
Palmer House a Hilton Hotel
8 Very good
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Philadelphia
Meals not included
3 nights + flight
C$ 756
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Philadelphia
Meals not included
3 nights + flight
C$ 644
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.3 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Denver Intl
Meals not included
3 nights + flight
C$ 1,068
Hyatt Place Chicago/River North - Chicago - Dining room
Hyatt Place Chicago/River North - Chicago - Dining room
Hyatt Place Chicago/River North
8.7 Very good
Near North Side
Free Wi-Fi
Philadelphia
Breakfast
3 nights + flight
C$ 717
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel
8.6 Very good
Downtown
Pet friendly
Spa
Columbus
Meals not included
3 nights + flight
C$ 819
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago
8.2 Very good
Near North Side
Pet friendly
Spa
Philadelphia
Meals not included
3 nights + flight
C$ 658
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
Columbus
Meals not included
3 nights + flight
C$ 801
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.7 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Philadelphia
Meals not included
3 nights + flight
C$ 1,405

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
Seattle/Tacoma Intl
All inclusive
3 nights + flight
C$ 1,267

Last minute vacation packages to Chicago

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The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
7.9 Good
Downtown
Pool
Pet friendly
Spa
Orlando
Meals not included
3 nights + flight
C$ 2,055
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
South Side
Free Wi-Fi
Orlando
Breakfast
3 nights + flight
C$ 1,264
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.3 Wonderful
Near West Side
Pool
Pet friendly
Orlando
Breakfast
3 nights + flight
C$ 1,491

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$ 89; Family vacation C$ 230; Romantic vacation C$ 242; Luxury vacation C$ 505; Budget vacation C$ 252.

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$ 89
Family vacation (Flight+Hotel)C$ 230
Romantic vacation (Flight+Hotel)C$ 242
Luxury vacation (Flight+Hotel)C$ 505
Budget vacation (Flight+Hotel)C$ 252