Vacations in Chicago
2 travelers
Thu 5/30
Sun 6/2
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Cheap Chicago package deals
Most popular Chicago flight and hotel deals
Show allLake View
Free Wi-Fi
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$395
Downtown
Free Wi-Fi
Miami
Meals not included
3 nights + flight
$361
Lake View
Free Wi-Fi
Pet friendly
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$380
Near West Side
Free Wi-Fi
Minneapolis St Paul
Breakfast
3 nights + flight
$378
Downtown
Free Wi-Fi
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$345
Downtown
Pool
Pet friendly
Minneapolis St Paul
Breakfast
3 nights + flight
$429
Downtown
Free Wi-Fi
Pool
Pet friendly
Newark
Meals not included
3 nights + flight
$400
Airport shuttle
Free Wi-Fi
Pool
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$414
Downtown
Free Wi-Fi
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$319
Downtown
Free Wi-Fi
Pet friendly
Spa
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$315
Downtown
Free Wi-Fi
Minneapolis St Paul
Meals not included
3 nights + flight
$349
Downtown
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$363
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
Pet friendly
Spa
Newark
Meals not included
3 nights + flight
$667
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$331
Downtown
Free Wi-Fi
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$443
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
$1,424
Fairmont Chicago at Millennium Park Gold Experience - Chicago - Bar![Fairmont Chicago at Millennium Park Gold Experience - Chicago - Bar]()
Fairmont Chicago at Millennium Park Gold Experience
Downtown
Free Wi-Fi
Pet friendly
New York LaGuardia
Breakfast
3 nights + flight
$1,140
Downtown
Free Wi-Fi
Pet friendly
Miami
Breakfast
3 nights + flight
$718
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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