Vacations in Chicago

Vacations in Chicago

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C$ 423 - C$ 703C$ 703 - C$ 983C$ 983 - C$ 1,263C$ 1,263 - C$ 1,543C$ 1,543+ per night

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Most popular Chicago flight and hotel deals

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Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG
8 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Portland
Meals not included
3 nights + flight
C$ 777
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
2.5 Poor
Chatham
Parking
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 436
Holiday Inn Express Chicago - Magnificent Mile By IHG - Chicago - Lobby
Holiday Inn Express Chicago - Magnificent Mile By IHG - Chicago - Lobby
Holiday Inn Express Chicago - Magnificent Mile By IHG
7.8 Good
Near North Side
Free Wi-Fi
Los Angeles
Breakfast
3 nights + flight
C$ 711
Chicago Marriott Downtown Magnificent Mile - Chicago - Building
Chicago Marriott Downtown Magnificent Mile - Chicago - Building
Chicago Marriott Downtown Magnificent Mile
8.3 Very good
Near North Side
Detroit Metropolitan Wayne County
Meals not included
3 nights + flight
C$ 832
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.3 Very good
Loop
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 676
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.9 Very good
Near West Side
Free Wi-Fi
Pet friendly
Cleveland Hopkins Intl
Breakfast
3 nights + flight
C$ 612
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 1,010
Motel Edgebrook Chicago North Shore By OYO - Chicago - Bedroom
Motel Edgebrook Chicago North Shore By OYO - Chicago - Bedroom
Motel Edgebrook Chicago North Shore By OYO
5.5 Fair
Forest Glen
Parking
Free Wi-Fi
Orlando
Meals not included
3 nights + flight
C$ 422
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton
8.8 Very good
Loop
Free Wi-Fi
Spa
Cleveland Hopkins Intl
Meals not included
3 nights + flight
C$ 799
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
Cleveland Hopkins Intl
Meals not included
3 nights + flight
C$ 665
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bar
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bar
La Quinta Inn & Suites by Wyndham Chicago Downtown
8 Very good
Loop
Free Wi-Fi
Pet friendly
Spa
Cleveland Hopkins Intl
Breakfast
3 nights + flight
C$ 684
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
Chinatown
Free Wi-Fi
Portland
Breakfast
3 nights + flight
C$ 695
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
Portland
Meals not included
3 nights + flight
C$ 808
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Building
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Building
SpringHill Suites by Marriott Chicago Downtown/River North
8.8 Very good
Near North Side
Free Wi-Fi
Portland
Breakfast
3 nights + flight
C$ 812
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago - Chicago - Bar
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago - Chicago - Bar
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
9 Wonderful
Near North Side
Pet friendly
Cleveland Hopkins Intl
Meals not included
3 nights + flight
C$ 1,370
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
Pet friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 1,358

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$ 1,303

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$ 87; Family vacation C$ 207; Romantic vacation C$ 248; Luxury vacation C$ 492; Budget vacation C$ 258.

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$ 87
Family vacation (Flight+Hotel)C$ 207
Romantic vacation (Flight+Hotel)C$ 248
Luxury vacation (Flight+Hotel)C$ 492
Budget vacation (Flight+Hotel)C$ 258