Vacations in Chicago

Vacations in Chicago

2 travellers

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Cheap Chicago package deals

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C$ 290 - C$ 659C$ 659 - C$ 1,027C$ 1,027 - C$ 1,395C$ 1,395 - C$ 1,764C$ 1,764+ per night

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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
Baltimore/Washington
Meals not included
3 nights + flight
C$ 359
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
9.1 Wonderful
Near North Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Breakfast
3 nights + flight
C$ 325
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 Very good
Near West Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Breakfast
3 nights + flight
C$ 462
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
Baltimore/Washington
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
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 687
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Raleigh-Durham
Meals not included
3 nights + flight
C$ 1,096
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$ 720
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
Nashville Intl
Breakfast
3 nights + flight
C$ 674
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
Baltimore/Washington
Meals not included
3 nights + flight
C$ 484
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
7.9 Good
Loop
Pool
Pet friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
C$ 1,763
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
Loop
Free Wi-Fi
Pet friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
C$ 556
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Fort Lauderdale
Meals not included
3 nights + flight
C$ 634
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Lobby
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Lobby
The Allegro Royal Sonesta Hotel Chicago Loop
8.4 Very good
Loop
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
C$ 461
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
Baltimore/Washington
Meals not included
3 nights + flight
C$ 781
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.1 Very good
Near North Side
Free Wi-Fi
Pool
Baltimore/Washington
Meals not included
3 nights + flight
C$ 581
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.8 Very good
Near North Side
Free Wi-Fi
Pool
Spa
Nashville Intl
Meals not included
3 nights + flight
C$ 1,306

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
Los Angeles Los Angeles
All inclusive
3 nights + flight
C$ 1,194

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
San Juan Luis Munoz Marin Intl
Meals not included
3 nights + flight
C$ 1,108
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.8 Very good
Near West Side
Free Wi-Fi
Pet friendly
San Juan Luis Munoz Marin Intl
Breakfast
3 nights + flight
C$ 956

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$ 84; Family vacation C$ 202; Romantic vacation C$ 241; Luxury vacation C$ 479; Budget vacation C$ 251.

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$ 84
Family vacation (Flight+Hotel)C$ 202
Romantic vacation (Flight+Hotel)C$ 241
Luxury vacation (Flight+Hotel)C$ 479
Budget vacation (Flight+Hotel)C$ 251