Vacations in Chicago
2 travelers
Wed 5/22
Sat 5/25
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Cheap Chicago package deals
Most popular Chicago flight and hotel deals
Show allWrigleyville
Free Wi-Fi
Pet friendly
El Paso
Meals not included
3 nights + flight
$324
Downtown
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$402
Downtown
Spa
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$454
West Town
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$519
The St. Regis Chicago - Chicago - Bedroom![The St. Regis Chicago - Chicago - Bedroom]()
The St. Regis Chicago
Downtown
Pool
Pet friendly
Spa
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$973
Downtown
Free Wi-Fi
Pool
Pet friendly
Orlando
Meals not included
3 nights + flight
$580
Downtown
Free Wi-Fi
Pet friendly
New Orleans Louis Armstrong
Breakfast
3 nights + flight
$435
Downtown
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$438
Sonder The Burnham - Chicago - Bedroom![Sonder The Burnham - Chicago - Bedroom]()
Sonder The Burnham
Downtown
Free Wi-Fi
Boston Logan Intl
Meals not included
3 nights + flight
$437
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$564
Downtown
Spa
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$498
Downtown
Free Wi-Fi
Los Angeles
Breakfast
3 nights + flight
$490
Downtown
Free Wi-Fi
Pet friendly
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$509
Downtown
Free Wi-Fi
Pool
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$397
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Los Angeles
Meals not included
3 nights + flight
$794
Last minute vacation packages to Chicago
Show allDowntown
Free Wi-Fi
Pool
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$486
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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