Vacations in Chicago
2 travelers
Fri 10/11
Mon 10/14
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Cheap Chicago package deals
Most popular Chicago flight and hotel deals
Show allDowntown
Free Wi-Fi
Pool
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
$402
Near West Side
Free Wi-Fi
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$252
Downtown
Free Wi-Fi
Pet friendly
New York LaGuardia
Breakfast
3 nights + flight
$398
Downtown
Free Wi-Fi
Pool
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$383
Downtown
Free Wi-Fi
Pet friendly
Spa
Denver Intl
Meals not included
3 nights + flight
$405
Downtown
Free Wi-Fi
Boston Logan Intl
Meals not included
3 nights + flight
$367
Downtown
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$323
Sonder The Burnham - Chicago - Bedroom![Sonder The Burnham - Chicago - Bedroom]()
Sonder The Burnham
Downtown
Free Wi-Fi
New York LaGuardia
Meals not included
3 nights + flight
$413
Downtown
Free Wi-Fi
Pet friendly
Spa
New York LaGuardia
Meals not included
3 nights + flight
$290
Near North Side
Free Wi-Fi
Pet friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$324
Downtown
Free Wi-Fi
Dallas/Fort Worth
Meals not included
3 nights + flight
$381
Downtown
Pet friendly
Spa
Denver Intl
Meals not included
3 nights + flight
$292
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Kansas City
Meals not included
3 nights + flight
$748
Downtown
Free Wi-Fi
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$196
Last minute vacation packages to Chicago
Show allDowntown
Free Wi-Fi
Pool
Los Angeles
Meals not included
3 nights + flight
$425
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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