Vacations in Chicago

Vacations in Chicago

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Cheap Chicago package deals

These are the best prices for Jun 20 - 23.
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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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C$ 312 - C$ 620C$ 620 - C$ 931C$ 931 - C$ 1,240C$ 1,240 - C$ 1,550C$ 1,550+ per night

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Most popular Chicago flight and hotel deals

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Thompson Chicago - Chicago - Lobby
Thompson Chicago - Chicago - Lobby
Thompson Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 854
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 661
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Hotels Chicago Magnificent Mile By IHG
8.1 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Columbia Metropolitan
Meals not included
3 nights + flight
C$ 781
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.6 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 642
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical - Chicago - Lounge
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical - Chicago - Lounge
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
8.2 Very good
Near North Side
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
C$ 702
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
New York John F Kennedy Intl
Breakfast
3 nights + flight
C$ 863
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
8.2 Very good
O'Hare
Airport shuttle
Pool
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 601
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
Washington, D.C. Dulles Intl
Meals not included
3 nights + flight
C$ 770
The Chicago Hotel Collection Magnificent Mile - Chicago - Lounge
The Chicago Hotel Collection Magnificent Mile - Chicago - Lounge
The Chicago Hotel Collection Magnificent Mile
7.5 Good
Near North Side
Washington, D.C. Dulles Intl
Meals not included
3 nights + flight
C$ 618
The Whitehall Hotel, BW Premier Collection - Chicago - Bedroom
The Whitehall Hotel, BW Premier Collection - Chicago - Bedroom
The Whitehall Hotel, BW Premier Collection
7.9 Good
Near North Side
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 577
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 686
Hampton Inn Chicago Downtown/N Loop/Michigan Ave - Chicago - Lobby
Hampton Inn Chicago Downtown/N Loop/Michigan Ave - Chicago - Lobby
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
8 Very good
Downtown
Free Wi-Fi
Pet friendly
Columbia Metropolitan
Breakfast
3 nights + flight
C$ 756
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$ 1,072
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
Washington, D.C. Dulles Intl
Meals not included
3 nights + flight
C$ 835
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.6 Very good
Downtown
Free Wi-Fi
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 827
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
Washington, D.C. Dulles Intl
Meals not included
3 nights + flight
C$ 830

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
Newark
All inclusive
3 nights + flight
C$ 1,259

Last minute vacation packages to Chicago

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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
8.2 Very good
Near North Side
Free Wi-Fi
Pool
Newark
Meals not included
3 nights + flight
C$ 1,105
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
Newark
Breakfast
3 nights + flight
C$ 961
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Meeting room
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Meeting room
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
South Side
Free Wi-Fi
Newark
Breakfast
3 nights + flight
C$ 817

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$ 90; Family vacation C$ 232; Romantic vacation C$ 244; Luxury vacation C$ 510; Budget vacation C$ 254.

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$ 90
Family vacation (Flight+Hotel)C$ 232
Romantic vacation (Flight+Hotel)C$ 244
Luxury vacation (Flight+Hotel)C$ 510
Budget vacation (Flight+Hotel)C$ 254