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
Pool
Pet friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$461
Downtown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$309
Downtown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$346
Near West Side
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Breakfast
3 nights + flight
$286
O'Hare
Airport shuttle
Pool
Houston George Bush Intcntl
Meals not included
3 nights + flight
$332
Downtown
Pet friendly
Spa
Newark
Meals not included
3 nights + flight
$408
The Neighborhood Hotel-Little Italy - Chicago - Living room![The Neighborhood Hotel-Little Italy - Chicago - Living room]()
The Neighborhood Hotel-Little Italy
Near West Side
Raleigh-Durham
Meals not included
3 nights + flight
$499
Downtown
Free Wi-Fi
Pool
Pet friendly
Dallas/Fort Worth
Breakfast
3 nights + flight
$383
Downtown
Pool
Pet friendly
Spa
Raleigh-Durham
Meals not included
3 nights + flight
$760
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
$442
Downtown
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$399
Downtown
Free Wi-Fi
Pool
Pet friendly
Houston George Bush Intcntl
Breakfast
3 nights + flight
$373
Downtown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$309
Downtown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$422
Downtown
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$291
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
Downtown
Free Wi-Fi
Pool
Houston George Bush Intcntl
Meals not included
3 nights + flight
$574
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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