Vacations in Chicago
2 travelers
Tue 5/21
Fri 5/24
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Cheap Chicago package deals
Most popular Chicago flight and hotel deals
Show allDowntown
Free Wi-Fi
Pool
Pet friendly
Spa
Los Angeles
Meals not included
3 nights + flight
$754
Downtown
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$402
Downtown
Pool
Pet friendly
Raleigh-Durham
Breakfast
3 nights + flight
$450
O'Hare
Airport shuttle
Pool
Hartford Bradley Intl
Meals not included
3 nights + flight
$308
Downtown
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$332
Downtown
Pool
Spa
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$303
Downtown
Free Wi-Fi
Pet friendly
New Orleans Louis Armstrong
Breakfast
3 nights + flight
$435
Downtown
Pool
Pet friendly
Spa
Hartford Bradley Intl
Meals not included
3 nights + flight
$627
Downtown
Free Wi-Fi
Pet friendly
Orlando
Breakfast
3 nights + flight
$421
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$564
Downtown
Free Wi-Fi
Pool
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$397
Downtown
Free Wi-Fi
Pool
Pet friendly
Orlando
Breakfast
3 nights + flight
$354
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Los Angeles
Meals not included
3 nights + flight
$794
Downtown
Free Wi-Fi
Pool
Pet friendly
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$329
Last minute vacation packages to Chicago
Show allDowntown
Free Wi-Fi
Pool
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$486
Downtown
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$468
Downtown
Free Wi-Fi
Denver Intl
Breakfast
3 nights + flight
$570
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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