Vacations in Chicago
2 travelers
Sat 6/15
Tue 6/18
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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
$262
Downtown
Free Wi-Fi
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$272
Lake View
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$418
Downtown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Breakfast
3 nights + flight
$405
West Town
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
$465
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
Houston George Bush Intcntl
Breakfast
3 nights + flight
$302
Rogers Park
Free Wi-Fi
Pet friendly
Newark
Breakfast
3 nights + flight
$407
Downtown
Free Wi-Fi
Pet friendly
Spa
New York LaGuardia
Meals not included
3 nights + flight
$297
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
Los Angeles
Meals not included
3 nights + flight
$472
South Side
Free Wi-Fi
Pet friendly
New York LaGuardia
Breakfast
3 nights + flight
$356
Downtown
Free Wi-Fi
Pool
Pet friendly
Houston George Bush Intcntl
Breakfast
3 nights + flight
$373
Last minute vacation packages to Chicago
Show allChic and Furnished 1BR Apartment - Harlem B14 - Chicago![Chic and Furnished 1BR Apartment - Harlem B14 - Chicago]()
Chic and Furnished 1BR Apartment - Harlem B14
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$330
Chic Furnished Studio with Laundry Brompton 61-66 rep - Chicago![Chic Furnished Studio with Laundry Brompton 61-66 rep - Chicago]()
Chic Furnished Studio with Laundry Brompton 61-66 rep
Boystown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$342
Homey 2br Haven Fully Furnished! - Fullerton 1b - Chicago![Homey 2br Haven Fully Furnished! - Fullerton 1b - Chicago]()
Homey 2br Haven Fully Furnished! - Fullerton 1b
Albany Park
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$344
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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