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Vacations in Chicago

Vacations in Chicago

2 travellers

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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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C$ 419 - C$ 652C$ 652 - C$ 887C$ 887 - C$ 1,122C$ 1,122 - C$ 1,357C$ 1,357+ 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
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 470
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
Pool
Pet friendly
San Francisco
Meals not included
3 nights + flight
C$ 560
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.3 Very good
Loop
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 474
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel - Chicago - Restaurant
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel - Chicago - Restaurant
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 558
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
San Francisco
Meals not included
3 nights + flight
C$ 836
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 558
Hotel Felix - Chicago - Lobby
Hotel Felix - Chicago - Lobby
Hotel Felix
7.6 Good
Near North Side
Free Wi-Fi
Pet friendly
Spa
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 525
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
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 650
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
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
C$ 632
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
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 980
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
San Francisco
Meals not included
3 nights + flight
C$ 1,183
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel
8.1 Very good
Loop
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 479
Sofitel Chicago Magnificent Mile - Chicago - Lobby
Sofitel Chicago Magnificent Mile - Chicago - Lobby
Sofitel Chicago Magnificent Mile
8.9 Very good
Near North Side
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 706
Club Quarters Hotel Wacker at Michigan, Chicago - Chicago - Building
Club Quarters Hotel Wacker at Michigan, Chicago - Chicago - Building
Club Quarters Hotel Wacker at Michigan, Chicago
8.3 Very good
Loop
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 478
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
San Francisco
Meals not included
3 nights + flight
C$ 644
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.1 Good
Loop
Free Wi-Fi
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 504

Last minute vacation packages to Chicago

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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
Newark
Meals not included
3 nights + flight
C$ 1,556
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
7.9 Good
Near North Side
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
C$ 1,647
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
Houston George Bush Intcntl
Breakfast
3 nights + flight
C$ 1,856
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
Newark
Breakfast
3 nights + flight
C$ 1,536

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$ 101; Family vacation C$ 221; Romantic vacation C$ 250; Luxury vacation C$ 496; Budget vacation C$ 260.

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$ 101
Family vacation (Flight+Hotel)C$ 221
Romantic vacation (Flight+Hotel)C$ 250
Luxury vacation (Flight+Hotel)C$ 496
Budget vacation (Flight+Hotel)C$ 260