Vacations in Chicago

Vacations in Chicago

2 travellers

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Cheap Chicago package deals

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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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C$ 238 - C$ 492C$ 492 - C$ 747C$ 747 - C$ 1,000C$ 1,000 - C$ 1,254C$ 1,254+ per night

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Most popular Chicago flight and hotel deals

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Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.5 Very good
Near North Side
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
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
8.5 Very good
Near West Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Breakfast
3 nights + flight
C$ 379
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
New York LaGuardia
Meals not included
3 nights + flight
C$ 385
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
8 Very good
Near North Side
Pool
Pet friendly
New York LaGuardia
Breakfast
3 nights + flight
C$ 562
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
Baltimore/Washington
Meals not included
3 nights + flight
C$ 777
Chinatown Hotel Chicago - Chicago - Dining room
Chinatown Hotel Chicago - Chicago - Dining room
Chinatown Hotel Chicago
5.7 Fair
South Side
Free Wi-Fi
Newark
Meals not included
3 nights + flight
C$ 368
Fairmont Chicago Millennium Park - Chicago - Living room
Fairmont Chicago Millennium Park - Chicago - Living room
Fairmont Chicago Millennium Park
8.1 Very good
Downtown
Pet friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
C$ 472
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop
8.9 Very good
Downtown
Free Wi-Fi
Pet friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
C$ 409
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop
8.2 Very good
Downtown
Free Wi-Fi
Pool
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 429
Eurostars Magnificent Mile - Chicago - Lounge
Eurostars Magnificent Mile - Chicago - Lounge
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 401
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bedroom
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bedroom
La Quinta Inn & Suites by Wyndham Chicago Downtown
7.9 Good
Downtown
Free Wi-Fi
Pet friendly
Spa
Baltimore/Washington
Breakfast
3 nights + flight
C$ 426
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
7.8 Good
Downtown
Free Wi-Fi
Pet friendly
Baltimore/Washington
Breakfast
3 nights + flight
C$ 343
Hotel Chicago West Loop, SureStay Collection by Best Western - Chicago - Living room
Hotel Chicago West Loop, SureStay Collection by Best Western - Chicago - Living room
Hotel Chicago West Loop, SureStay Collection by Best Western
7.5 Good
Near West Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
C$ 359
The Drake - Chicago - Lobby
The Drake - Chicago - Lobby
The Drake
8.2 Very good
Near North Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
C$ 392
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
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
C$ 426
Virgin Hotels Chicago - Chicago - Building
Virgin Hotels Chicago - Chicago - Building
Virgin Hotels Chicago
8.6 Very good
Downtown
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
C$ 469

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
Fort Myers SW Florida Intl
All inclusive
3 nights + flight
C$ 1,360

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
8.5 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
C$ 1,028
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Minneapolis St Paul
Meals not included
3 nights + flight
C$ 1,534
Courtyard Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard Chicago Downtown/Magnificent Mile
8.4 Very good
Near North Side
Free Wi-Fi
Pool
Cleveland Hopkins Intl
Meals not included
3 nights + flight
C$ 981

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$ 742; Family vacation C$ 673; Romantic vacation C$ 784; Luxury vacation C$ 777; Budget vacation C$ 553.

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$ 742
Family vacation (Flight+Hotel)C$ 673
Romantic vacation (Flight+Hotel)C$ 784
Luxury vacation (Flight+Hotel)C$ 777
Budget vacation (Flight+Hotel)C$ 553

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