Vacations in Chicago

Vacations in Chicago

2 travelers

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Cheap Chicago package deals

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$234 - $408$408 - $581$581 - $754$754 - $928$928+ per night

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Most popular Chicago flight and hotel deals

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Thompson Chicago - Chicago - Living room
Thompson Chicago - Chicago - Living room
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
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
Raleigh-Durham
Meals not included
3 nights + flight
$340
Chicago Marriott Downtown Magnificent Mile - Chicago - Bedroom
Chicago Marriott Downtown Magnificent Mile - Chicago - Bedroom
Chicago Marriott Downtown Magnificent Mile
8.2 Very good
Near North Side
San Francisco
Meals not included
3 nights + flight
$486
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
New York LaGuardia
Breakfast
3 nights + flight
$391
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
New York LaGuardia
Breakfast
3 nights + flight
$464
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
7.9 Good
Near North Side
Pool
Pet friendly
Newark
Breakfast
3 nights + flight
$388
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
San Francisco
Meals not included
3 nights + flight
$491
21c Museum Hotel Chicago - Chicago - Restaurant
21c Museum Hotel Chicago - Chicago - Restaurant
21c Museum Hotel Chicago
8.4 Very good
Near North Side
Free Wi-Fi
Pet friendly
San Francisco
Meals not included
3 nights + flight
$472
Millennium Knickerbocker Chicago - Chicago - Bedroom
Millennium Knickerbocker Chicago - Chicago - Bedroom
Millennium Knickerbocker Chicago
7.8 Good
Near North Side
Detroit Metropolitan Wayne County
Meals not included
3 nights + flight
$348
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.7 Very good
Downtown
Pool
Pet friendly
Spa
Pittsburgh
Meals not included
3 nights + flight
$1,249
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Lounge
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Lounge
SpringHill Suites by Marriott Chicago Downtown/River North
8.7 Very good
Near North Side
Free Wi-Fi
Boston Logan Intl
Breakfast
3 nights + flight
$458
The Willows Hotel - Chicago - Lobby
The Willows Hotel - Chicago - Lobby
The Willows Hotel
8 Very good
Lake View
Free Wi-Fi
Dallas/Fort Worth
Meals not included
3 nights + flight
$410
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
8.9 Very good
Near North Side
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$658
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
Boston Logan Intl
Meals not included
3 nights + flight
$860
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
Downtown
Free Wi-Fi
Pet friendly
Newark
Meals not included
3 nights + flight
$431
Congress Plaza Hotel - Chicago - Living room
Congress Plaza Hotel - Chicago - Living room
Congress Plaza Hotel
7.3 Good
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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Hyatt Regency Mccormick Place - Chicago - Patio
Hyatt Regency Mccormick Place - Chicago - Patio
Hyatt Regency Mccormick Place
8.6 Very good
Near South Side
Free Wi-Fi
Pool
Nashville Intl
Meals not included
3 nights + flight
$507
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room
The Allegro Royal Sonesta Hotel Chicago Loop
8.4 Very good
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.

Everything you need to know for your vacation in Chicago

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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