Vacations in Chicago
2 travelers
Wed 6/12
Sat 6/15
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Cheap Chicago package deals
Most popular Chicago flight and hotel deals
Show allDowntown
Free Wi-Fi
Pet friendly
Salt Lake City
Meals not included
3 nights + flight
$468
Downtown
Free Wi-Fi
Pool
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$566
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Nashville Intl
Meals not included
3 nights + flight
$631
Downtown
Free Wi-Fi
Spa
Akron/Canton
Meals not included
3 nights + flight
$459
Downtown
Pet friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$405
Downtown
Pool
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$381
Downtown
Pool
Pet friendly
Spa
Salt Lake City
Meals not included
3 nights + flight
$756
Sonder The Burnham - Chicago - Bedroom![Sonder The Burnham - Chicago - Bedroom]()
Sonder The Burnham
Downtown
Free Wi-Fi
Lexington Blue Grass
Meals not included
3 nights + flight
$421
Downtown
Pet friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$504
Downtown
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
$287
Downtown
Free Wi-Fi
Pet friendly
Spa
Salt Lake City
Meals not included
3 nights + flight
$390
Near North Side
Free Wi-Fi
Pet friendly
Spa
Minneapolis St Paul
Meals not included
3 nights + flight
$410
Downtown
Free Wi-Fi
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
$507
Downtown
Free Wi-Fi
Pet friendly
Akron/Canton
Meals not included
3 nights + flight
$473
Downtown
Free Wi-Fi
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$424
Last minute vacation packages to Chicago
Show allDowntown
Free Wi-Fi
Pool
Pet friendly
Los Angeles
Meals not included
3 nights + flight
$947
Downtown
Pet friendly
Tampa
Meals not included
3 nights + flight
$1,160
Downtown
Free Wi-Fi
Los Angeles
Meals not included
3 nights + flight
$1,004
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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