Vacations in Chicago
2 travelers
Thu 6/13
Sun 6/16
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Cheap Chicago package deals
Most popular Chicago flight and hotel deals
Show allWest Lawn
Airport shuttle
Free Wi-Fi
New York LaGuardia
Meals not included
3 nights + flight
$330
Downtown
Free Wi-Fi
Pet friendly
Akron/Canton
Meals not included
3 nights + flight
$350
Chic and Furnished 1BR Apartment - Harlem B14 - Chicago![Chic and Furnished 1BR Apartment - Harlem B14 - Chicago]()
Chic and Furnished 1BR Apartment - Harlem B14
Free Wi-Fi
Philadelphia
Meals not included
3 nights + flight
$243
Downtown
Free Wi-Fi
Pool
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$471
Near West Side
Free Wi-Fi
Pet friendly
Philadelphia
Breakfast
3 nights + flight
$390
Downtown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$437
Downtown
Free Wi-Fi
Pet friendly
Boston Logan Intl
Breakfast
3 nights + flight
$460
Downtown
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$354
Sonder The Burnham - Chicago - Bedroom![Sonder The Burnham - Chicago - Bedroom]()
Sonder The Burnham
Downtown
Free Wi-Fi
Dallas/Fort Worth
Meals not included
3 nights + flight
$440
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Nashville Intl
Meals not included
3 nights + flight
$657
Downtown
Free Wi-Fi
Pet friendly
New York LaGuardia
Meals not included
3 nights + flight
$456
Downtown
Free Wi-Fi
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
$452
Downtown
Free Wi-Fi
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
$340
Last minute vacation packages to Chicago
Show allDowntown
Free Wi-Fi
Pool
Pet friendly
Detroit Metropolitan Wayne County
Meals not included
3 nights + flight
$1,068
Downtown
Free Wi-Fi
Pet friendly
Detroit Metropolitan Wayne County
Breakfast
3 nights + flight
$1,002
Downtown
Free Wi-Fi
Detroit Metropolitan Wayne County
Breakfast
3 nights + flight
$1,283
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 |
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