Vacations in Chicago
2 travelers
Mon 6/17
Thu 6/20
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Cheap Chicago package deals
Most popular Chicago flight and hotel deals
Show allDowntown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$281
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Building![Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Building]()
Residence Inn by Marriott Chicago Downtown Magnificent Mile
Downtown
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
$450
Downtown
Free Wi-Fi
Pet friendly
Los Angeles
Breakfast
3 nights + flight
$408
Near West Side
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Breakfast
3 nights + flight
$286
Downtown
Free Wi-Fi
Spa
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$399
Downtown
Free Wi-Fi
Pool
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$374
Boystown
Free Wi-Fi
Pet friendly
Spa
Charlotte Douglas
Meals not included
3 nights + flight
$482
The Neighborhood Hotel-Little Italy - Chicago - Living room![The Neighborhood Hotel-Little Italy - Chicago - Living room]()
The Neighborhood Hotel-Little Italy
Near West Side
Houston George Bush Intcntl
Meals not included
3 nights + flight
$404
Downtown
Free Wi-Fi
Pool
Pet friendly
Phoenix Sky Harbor Intl
Breakfast
3 nights + flight
$371
Downtown
Free Wi-Fi
New York LaGuardia
Meals not included
3 nights + flight
$332
Sonder The Burnham - Chicago - Bedroom![Sonder The Burnham - Chicago - Bedroom]()
Sonder The Burnham
Downtown
Free Wi-Fi
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$386
Downtown
Free Wi-Fi
Pool
Houston George Bush Intcntl
Meals not included
3 nights + flight
$284
Downtown
Free Wi-Fi
Pet friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$346
Downtown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$349
Downtown
Free Wi-Fi
Pet friendly
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$377
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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