Vacations in Chicago
2 travelers
Fri 5/31
Mon 6/3
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Cheap Chicago package deals
Most popular Chicago flight and hotel deals
Show allDowntown
Pet friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
$454
Downtown
Free Wi-Fi
Minneapolis St Paul
Meals not included
3 nights + flight
$390
Near West Side
Free Wi-Fi
Newark
Breakfast
3 nights + flight
$407
Downtown
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$394
Downtown
Free Wi-Fi
Pool
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
$551
Downtown
Free Wi-Fi
Pool
Pet friendly
Newark
Meals not included
3 nights + flight
$400
Airport shuttle
Free Wi-Fi
Pool
Dallas/Fort Worth
Meals not included
3 nights + flight
$413
Downtown
Free Wi-Fi
Pet friendly
Spa
Charlotte Douglas
Meals not included
3 nights + flight
$409
Downtown
Free Wi-Fi
Minneapolis St Paul
Meals not included
3 nights + flight
$422
Downtown
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$363
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
$729
Sonder The Burnham - Chicago - Bedroom![Sonder The Burnham - Chicago - Bedroom]()
Sonder The Burnham
Downtown
Free Wi-Fi
Newark
Meals not included
3 nights + flight
$421
Downtown
Free Wi-Fi
Pool
Charlotte Douglas
Meals not included
3 nights + flight
$478
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Fort Lauderdale
Meals not included
3 nights + flight
$361
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Newark
Meals not included
3 nights + flight
$509
Last minute vacation packages to Chicago
Show allThe St. Regis Chicago - Chicago - Bedroom![The St. Regis Chicago - Chicago - Bedroom]()
The St. Regis Chicago
Downtown
Pool
Pet friendly
Spa
Miami
Meals not included
3 nights + flight
$1,379
Downtown
Free Wi-Fi
Pet friendly
Miami
Breakfast
3 nights + flight
$774
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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