Vacations in Chicago
2 travelers
Sat 6/29
Tue 7/2
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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
$333
Downtown
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$459
Downtown
Free Wi-Fi
Pet friendly
New York LaGuardia
Breakfast
3 nights + flight
$310
O'Hare
Airport shuttle
Pool
New York LaGuardia
Meals not included
3 nights + flight
$330
Downtown
Free Wi-Fi
New York LaGuardia
Meals not included
3 nights + flight
$368
Downtown
Free Wi-Fi
Spa
New York LaGuardia
Meals not included
3 nights + flight
$410
Downtown
Free Wi-Fi
Pool
Pet friendly
New York LaGuardia
Meals not included
3 nights + flight
$393
Free Wi-Fi
Pool
Houston George Bush Intcntl
Meals not included
3 nights + flight
$532
Boystown
Free Wi-Fi
Pet friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$542
Downtown
Free Wi-Fi
Pet friendly
Spa
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$487
Downtown
Free Wi-Fi
Pet friendly
Spa
New York LaGuardia
Meals not included
3 nights + flight
$340
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
New York LaGuardia
Meals not included
3 nights + flight
$646
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
New York LaGuardia
Breakfast
3 nights + flight
$365
Downtown
Free Wi-Fi
Pet friendly
New York LaGuardia
Meals not included
3 nights + flight
$370
Last minute vacation packages to Chicago
Show allThe Neighborhood Hotel-Little Italy - Chicago![The Neighborhood Hotel-Little Italy - Chicago]()
The Neighborhood Hotel-Little Italy
Near West Side
Fort Lauderdale
Meals not included
3 nights + flight
$669
The Elements by Cloud9 at West Loop Apt w full amenities -1044 - Chicago![The Elements by Cloud9 at West Loop Apt w full amenities -1044 - Chicago]()
The Elements by Cloud9 at West Loop Apt w full amenities -1044
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$850
Sonder The Burnham - Chicago![Sonder The Burnham - Chicago]()
Sonder The Burnham
Downtown
Free Wi-Fi
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$574
Near West Side
Free Wi-Fi
Pet friendly
Fort Lauderdale
Breakfast
3 nights + flight
$457
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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