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$ 570C$ 570 - C$ 904C$ 904 - C$ 1,238C$ 1,238 - C$ 1,570C$ 1,570+ per night

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Most popular Chicago flight and hotel deals

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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
8.1 Very good
Near North Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Breakfast
3 nights + flight
C$ 330
Residence Inn by Marriott Chicago Downtown/River North - Chicago - Lounge
Residence Inn by Marriott Chicago Downtown/River North - Chicago - Lounge
Residence Inn by Marriott Chicago Downtown/River North
8.4 Very good
Near North Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Breakfast
3 nights + flight
C$ 362
Hyatt Centric Chicago Magnificent Mile - Chicago - Bedroom
Hyatt Centric Chicago Magnificent Mile - Chicago - Bedroom
Hyatt Centric Chicago Magnificent Mile
8.5 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
C$ 348
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
C$ 494
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton
9 Wonderful
Downtown
Free Wi-Fi
Spa
Baltimore/Washington
Meals not included
3 nights + flight
C$ 331
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
Baltimore/Washington
Meals not included
3 nights + flight
C$ 347
Hampton Inn & Suites Chicago-Downtown - Chicago - Lobby
Hampton Inn & Suites Chicago-Downtown - Chicago - Lobby
Hampton Inn & Suites Chicago-Downtown
8.5 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Baltimore/Washington
Breakfast
3 nights + flight
C$ 280
Fairmont Chicago, Millenium Park - Chicago - Living room
Fairmont Chicago, Millenium Park - Chicago - Living room
Fairmont Chicago, Millenium Park
8.1 Very good
Downtown
Free Wi-Fi
Pet friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
C$ 425
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.8 Very good
Downtown
Pool
Pet friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 1,399
The Whitehall Hotel, BW Premier Collection - Chicago - Restaurant
The Whitehall Hotel, BW Premier Collection - Chicago - Restaurant
The Whitehall Hotel, BW Premier Collection
7.7 Good
Near North Side
Free Wi-Fi
Pet friendly
Orlando
Breakfast
3 nights + flight
C$ 314
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Orlando
Meals not included
3 nights + flight
C$ 654
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
Orlando
Breakfast
3 nights + flight
C$ 514
The Drake - Chicago - Lobby
The Drake - Chicago - Lobby
The Drake
8.2 Very good
Near North Side
Free Wi-Fi
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
C$ 568
Holiday Inn & Suites Chicago-Downtown By IHG - Chicago - Lounge
Holiday Inn & Suites Chicago-Downtown By IHG - Chicago - Lounge
Holiday Inn & Suites Chicago-Downtown By IHG
8 Very good
Near West Side
Free Wi-Fi
Pool
Orlando
Meals not included
3 nights + flight
C$ 463
Virgin Hotels Chicago - Chicago - Building
Virgin Hotels Chicago - Chicago - Building
Virgin Hotels Chicago
8.6 Very good
Downtown
Free Wi-Fi
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
C$ 536
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection
8.5 Very good
Near North Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
C$ 315

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
Orlando
All inclusive
3 nights + flight
C$ 1,379

Last minute vacation packages to Chicago

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The Burnham, Sonder Apartment by Marriott Bonvoy - Chicago - Living room
The Burnham, Sonder Apartment by Marriott Bonvoy - Chicago - Living room
The Burnham, Sonder Apartment by Marriott Bonvoy
8.1 Very good
Near West Side
Free Wi-Fi
Newark
Meals not included
3 nights + flight
C$ 923
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
Newark
Meals not included
3 nights + flight
C$ 602
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
Newark
Breakfast
3 nights + flight
C$ 859

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$ 743; Family vacation C$ 673; Romantic vacation C$ 785; Luxury vacation C$ 777; Budget vacation C$ 554.

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$ 743
Family vacation (Flight+Hotel)C$ 673
Romantic vacation (Flight+Hotel)C$ 785
Luxury vacation (Flight+Hotel)C$ 777
Budget vacation (Flight+Hotel)C$ 554

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