Vacations in Chicago
2 travelers
Sat 5/11
Tue 5/14
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Cheap Chicago package deals
Most popular Chicago flight and hotel deals
Show allDowntown
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
$348
Downtown
Free Wi-Fi
Pool
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$353
Downtown
Free Wi-Fi
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$250
Downtown
Free Wi-Fi
Pool
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$362
Downtown
Free Wi-Fi
Pet friendly
Spa
Denver Intl
Meals not included
3 nights + flight
$300
Downtown
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$270
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$585
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Dallas/Fort Worth
Meals not included
3 nights + flight
$313
Downtown
Free Wi-Fi
Dallas/Fort Worth
Meals not included
3 nights + flight
$351
Downtown
Free Wi-Fi
Pool
Pet friendly
Dallas/Fort Worth
Breakfast
3 nights + flight
$347
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$691
Downtown
Free Wi-Fi
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$267
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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