Vacations in Chicago
2 travelers
Sat 6/8
Tue 6/11
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Cheap Chicago package deals
Most popular Chicago flight and hotel deals
Show allDowntown
Free Wi-Fi
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
$480
Near North Side
Free Wi-Fi
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$317
Downtown
Free Wi-Fi
Pet friendly
New York LaGuardia
Meals not included
3 nights + flight
$434
Downtown
Free Wi-Fi
Spa
Minneapolis St Paul
Meals not included
3 nights + flight
$388
Airport shuttle
Free Wi-Fi
Pool
Kansas City
Meals not included
3 nights + flight
$442
Downtown
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
$342
Downtown
Free Wi-Fi
Minneapolis St Paul
Meals not included
3 nights + flight
$338
Downtown
Pet friendly
Los Angeles
Meals not included
3 nights + flight
$349
Downtown
Free Wi-Fi
Pet friendly
Minneapolis St Paul
Breakfast
3 nights + flight
$403
Sonder The Burnham - Chicago - Bedroom![Sonder The Burnham - Chicago - Bedroom]()
Sonder The Burnham
Downtown
Free Wi-Fi
Boston Logan Intl
Meals not included
3 nights + flight
$458
Downtown
Free Wi-Fi
Pool
Dallas/Fort Worth
Meals not included
3 nights + flight
$473
Downtown
Free Wi-Fi
Los Angeles
Meals not included
3 nights + flight
$399
Downtown
Free Wi-Fi
Los Angeles
Meals not included
3 nights + flight
$426
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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