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Vacations in Chicago

Vacations in Chicago

2 travelers

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$204 - $434$434 - $663$663 - $893$893 - $1,122$1,122+ 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
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$369
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
$260
Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94
2.5 Poor
Chatham
Parking
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
$217
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
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$345
Hilton Chicago - Chicago - Living room
Hilton Chicago - Chicago - Living room
Hilton Chicago
7.9 Good
Loop
Pool
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$378
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
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
$431
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
$302
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
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$423
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
$331
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop
8.6 Very good
Loop
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
$346
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
Los Angeles
Meals not included
3 nights + flight
$622
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
8.1 Very good
Near North Side
Free Wi-Fi
Pool
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$341
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk
8.4 Very good
Loop
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$266
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
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
$373
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
Orlando
Meals not included
3 nights + flight
$908
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago
8.5 Very good
Loop
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$340

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