Vacations in Chicago

Vacations in Chicago

2 travelers

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Vacation information

Cheap Chicago package deals

Discover the best prices by selecting your travel dates on KAYAK.

Most popular Chicago flight and hotel deals

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Thompson Chicago
8.7 Very good
Near North Side
Free Wi-Fi
Pet friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
$485
Near North Side
Free Wi-Fi
Pool
Pet friendly
Raleigh-Durham
Meals not included
3 nights + flight
$340
Near North Side
San Francisco
Meals not included
3 nights + flight
$486
Near North Side
Free Wi-Fi
Pet friendly
New York LaGuardia
Breakfast
3 nights + flight
$391
Near West Side
Free Wi-Fi
Pet friendly
New York LaGuardia
Breakfast
3 nights + flight
$464
L7 Chicago by LOTTE
9.1 Wonderful
Downtown
Free Wi-Fi
Pet friendly
San Francisco
Meals not included
3 nights + flight
$491
Near North Side
Free Wi-Fi
Pet friendly
San Francisco
Meals not included
3 nights + flight
$472
Near North Side
Detroit Metropolitan Wayne County
Meals not included
3 nights + flight
$348
Downtown
Pool
Pet friendly
Spa
Pittsburgh
Meals not included
3 nights + flight
$1,249
Near North Side
Free Wi-Fi
Boston Logan Intl
Breakfast
3 nights + flight
$458
Lake View
Free Wi-Fi
Dallas/Fort Worth
Meals not included
3 nights + flight
$410
Near North Side
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$658
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Boston Logan Intl
Meals not included
3 nights + flight
$860
Downtown
Free Wi-Fi
Pet friendly
Newark
Meals not included
3 nights + flight
$431
Downtown
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$323

Last minute vacation packages to Chicago

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Near South Side
Free Wi-Fi
Pool
Nashville Intl
Meals not included
3 nights + flight
$507
Downtown
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
$477

When to book a vacation in Chicago

Price includes flights and 3 nights accommodation for 2 travelers. 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 travelers: Top vacation $312; Family vacation $302; Romantic vacation $332; Luxury vacation $320; Budget vacation $237.

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.

Chicago vacation information

Top vacation (Flight+Hotel)$312
Family vacation (Flight+Hotel)$302
Romantic vacation (Flight+Hotel)$332
Luxury vacation (Flight+Hotel)$320
Budget vacation (Flight+Hotel)$237

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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