Vacations in Chicago
2 travelers
Sun 6/2
Wed 6/5
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Cheap Chicago package deals
Most popular Chicago flight and hotel deals
Show allNear West Side
Free Wi-Fi
Boston Logan Intl
Breakfast
3 nights + flight
$353
Downtown
Free Wi-Fi
Spa
Minneapolis St Paul
Meals not included
3 nights + flight
$446
Boystown
Free Wi-Fi
Pet friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
$434
Downtown
Free Wi-Fi
Minneapolis St Paul
Meals not included
3 nights + flight
$366
Downtown
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$390
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
$729
Downtown
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
$310
Sonder The Burnham - Chicago - Bedroom![Sonder The Burnham - Chicago - Bedroom]()
Sonder The Burnham
Downtown
Free Wi-Fi
Dallas/Fort Worth
Meals not included
3 nights + flight
$449
Downtown
Free Wi-Fi
Pool
Pet friendly
San Antonio
Meals not included
3 nights + flight
$381
Downtown
Free Wi-Fi
Pool
Pet friendly
San Antonio
Meals not included
3 nights + flight
$388
O'Hare
Airport shuttle
Free Wi-Fi
Pool
San Antonio
Meals not included
3 nights + flight
$357
Downtown
Free Wi-Fi
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$466
Downtown
Free Wi-Fi
Pool
Pet friendly
San Antonio
Breakfast
3 nights + flight
$495
Downtown
Free Wi-Fi
Asheville Regional
Meals not included
3 nights + flight
$473
Downtown
Free Wi-Fi
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$494
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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