Vacations in Chicago

Vacations in Chicago

2 travelers

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$238 - $417$417 - $596$596 - $775$775 - $954$954+ per night

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Most popular Chicago flight and hotel deals

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Thompson Chicago - Chicago - Lobby
Thompson Chicago - Chicago - Lobby
Thompson Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$373
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet friendly
Charlotte Douglas
Meals not included
3 nights + flight
$356
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
Minneapolis St Paul
Meals not included
3 nights + flight
$429
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.4 Very good
Near North Side
Pool
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$327
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
Spa
Minneapolis St Paul
Breakfast
3 nights + flight
$274
Hampton Inn Majestic Chicago Theatre District - Chicago - Building
Hampton Inn Majestic Chicago Theatre District - Chicago - Building
Hampton Inn Majestic Chicago Theatre District
8.6 Very good
Loop
Pet friendly
Minneapolis St Paul
Breakfast
3 nights + flight
$378
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
Charlotte Douglas
Meals not included
3 nights + flight
$372
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.4 Wonderful
Near West Side
Pool
Pet friendly
Minneapolis St Paul
Breakfast
3 nights + flight
$314
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop
8.9 Very good
Loop
Free Wi-Fi
Pet friendly
Spa
Minneapolis St Paul
Meals not included
3 nights + flight
$405
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Minneapolis St Paul
Meals not included
3 nights + flight
$302
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
Minneapolis St Paul
Meals not included
3 nights + flight
$338
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.3 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Charlotte Douglas
Meals not included
3 nights + flight
$659
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Building
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Building
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.2 Very good
Near North Side
Free Wi-Fi
Pool
Spa
Minneapolis St Paul
Meals not included
3 nights + flight
$326
Hotel Riu Plaza Chicago - Chicago - Lounge
Hotel Riu Plaza Chicago - Chicago - Lounge
Hotel Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Minneapolis St Paul
Breakfast
3 nights + flight
$377
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
Minneapolis St Paul
Breakfast
3 nights + flight
$369
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
Charlotte Douglas
Meals not included
3 nights + flight
$718

Last minute vacation packages to Chicago

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Warwick Allerton Chicago - Chicago - Building
Warwick Allerton Chicago - Chicago - Building
Warwick Allerton Chicago
8.1 Very good
Near North Side
New York LaGuardia
Meals not included
3 nights + flight
$926
The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy
Near West Side
Pet friendly
Newark
Meals not included
3 nights + flight
$795

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 $116; Family vacation $278; Romantic vacation $324; Luxury vacation $426; Budget vacation $251.

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)$116
Family vacation (Flight+Hotel)$278
Romantic vacation (Flight+Hotel)$324
Luxury vacation (Flight+Hotel)$426
Budget vacation (Flight+Hotel)$251