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$ 306 - C$ 522C$ 522 - C$ 739C$ 739 - C$ 956C$ 956 - C$ 1,171C$ 1,171+ per night

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Free breakfastFree internetFree airport shuttleFree parking

Most popular Chicago flight and hotel deals

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Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel
8.7 Very good
Near North Side
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 617
Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom
Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom
Admiral Motel By OYO Chicago I-94
4.8 Mediocre
South Side
Parking
Pet friendly
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
C$ 305
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
Pool
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 430
Hilton Chicago - Chicago - Living room
Hilton Chicago - Chicago - Living room
Hilton Chicago
7.8 Good
Downtown
Free Wi-Fi
Pool
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 549
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.4 Very good
Near West Side
Free Wi-Fi
Pet friendly
Los Angeles
Breakfast
3 nights + flight
C$ 533
21c Museum Hotel Chicago - Chicago - Restaurant
21c Museum Hotel Chicago - Chicago - Restaurant
21c Museum Hotel Chicago
8.5 Very good
Near North Side
Free Wi-Fi
Pet friendly
Raleigh-Durham
Meals not included
3 nights + flight
C$ 619
The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy
Near West Side
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 726
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
Raleigh-Durham
Meals not included
3 nights + flight
C$ 664
Hotel Felix Chicago - Chicago - Lobby
Hotel Felix Chicago - Chicago - Lobby
Hotel Felix Chicago
7.6 Good
Near North Side
Free Wi-Fi
Pet friendly
Spa
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 509
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bar
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bar
Hilton Garden Inn Chicago Downtown Riverwalk
8.4 Very good
Downtown
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 444
Best Motel By OYO Chicago I-90 - Chicago - Bedroom
Best Motel By OYO Chicago I-90 - Chicago - Bedroom
Best Motel By OYO Chicago I-90
1.7 Poor
South Side
Parking
Pet friendly
Knoxville McGhee Tyson
Meals not included
3 nights + flight
C$ 329
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
Breakfast
3 nights + flight
C$ 606
The Willows Hotel - Chicago - Lobby
The Willows Hotel - Chicago - Lobby
The Willows Hotel
8 Very good
Lake View
Free Wi-Fi
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
C$ 488
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
Los Angeles
Meals not included
3 nights + flight
C$ 1,152
The Talbott Hotel - Chicago - Bedroom
The Talbott Hotel - Chicago - Bedroom
The Talbott Hotel
8.6 Very good
Near North Side
Free Wi-Fi
Pet friendly
Raleigh-Durham
Meals not included
3 nights + flight
C$ 675
Club Quarters Hotel Central Loop, Chicago - Chicago - Lobby
Club Quarters Hotel Central Loop, Chicago - Chicago - Lobby
Club Quarters Hotel Central Loop, Chicago
8.1 Very good
Downtown
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 461

Last minute vacation packages to Chicago

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Intercontinental Chicago Magnificent Mile, An IHG Hotel - Chicago - Lobby
Intercontinental Chicago Magnificent Mile, An IHG Hotel - Chicago - Lobby
Intercontinental Chicago Magnificent Mile, An IHG Hotel
8 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
C$ 881
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 Very good
Near North Side
Free Wi-Fi
Pet friendly
Charlotte Douglas
Breakfast
3 nights + flight
C$ 729
L7 Chicago by LOTTE - Chicago - Lounge
L7 Chicago by LOTTE - Chicago - Lounge
L7 Chicago by LOTTE
9.1 Wonderful
Downtown
Free Wi-Fi
Pet friendly
Charlotte Douglas
Meals not included
3 nights + flight
C$ 751
Chicago Getaway Hostel - Chicago - Lobby
Chicago Getaway Hostel - Chicago - Lobby
Chicago Getaway Hostel
8.4 Very good
Lincoln Park
Free Wi-Fi
Nashville Intl
Meals not included
3 nights + flight
C$ 516

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$ 723; Family vacation C$ 656; Romantic vacation C$ 764; Luxury vacation C$ 757; Budget vacation C$ 539.

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$ 723
Family vacation (Flight+Hotel)C$ 656
Romantic vacation (Flight+Hotel)C$ 764
Luxury vacation (Flight+Hotel)C$ 757
Budget vacation (Flight+Hotel)C$ 539

Chicago vacation: Search Chicago vacation packages on KAYAK. KAYAK is a travel tool that searches Chicago trips on hundreds of travel sites to help you find the Chicago package that suits you best. Discover Chicago deals now and book your Chicago flight and hotel today.

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