Vacations in Chicago
2 travelers
Tue 5/28
Fri 5/31
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Cheap Chicago package deals
Most popular Chicago flight and hotel deals
Show allDowntown
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$322
Near West Side
Free Wi-Fi
Charlotte Douglas
Breakfast
3 nights + flight
$327
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Austin Bergstrom
Meals not included
3 nights + flight
$621
Downtown
Free Wi-Fi
Pool
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$431
Downtown
Free Wi-Fi
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$248
Downtown
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$299
Sonder The Burnham - Chicago - Bedroom![Sonder The Burnham - Chicago - Bedroom]()
Sonder The Burnham
Downtown
Free Wi-Fi
Denver Intl
Meals not included
3 nights + flight
$326
Downtown
Free Wi-Fi
Pool
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$404
Downtown
Free Wi-Fi
Denver Intl
Meals not included
3 nights + flight
$360
Downtown
Free Wi-Fi
Pool
Denver Intl
Meals not included
3 nights + flight
$329
Downtown
Free Wi-Fi
Pet friendly
Charlotte Douglas
Meals not included
3 nights + flight
$384
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Kansas City
Meals not included
3 nights + flight
$937
Downtown
Free Wi-Fi
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$338
Last minute vacation packages to Chicago
Show allDowntown
Free Wi-Fi
Pet friendly
New York John F Kennedy Intl
Breakfast
3 nights + flight
$716
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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