Vacations in Chicago
2 travelers
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Cheap Chicago package deals
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Most popular Chicago flight and hotel deals
Show allNear North Side
Free Wi-Fi
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
$383
Near North Side
Free Wi-Fi
Pool
Pet friendly
Burbank Bob Hope
Meals not included
3 nights + flight
$346
Near North Side
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
$442
Near North Side
Free Wi-Fi
Pet friendly
Boston Logan Intl
Breakfast
3 nights + flight
$380
Downtown
Pet friendly
Newark
Breakfast
3 nights + flight
$396
Near West Side
Pool
Pet friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
$407
Near North Side
Free Wi-Fi
Pool
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
$424
Near West Side
Free Wi-Fi
Newark
Meals not included
3 nights + flight
$435
Downtown
Pet friendly
Spa
Burbank Bob Hope
Meals not included
3 nights + flight
$370
Near West Side
Minneapolis St Paul
Meals not included
3 nights + flight
$505
Downtown
Pet friendly
Burbank Bob Hope
Meals not included
3 nights + flight
$336
Downtown
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
$415
Near North Side
Free Wi-Fi
Pool
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
$413
South Side
Free Wi-Fi
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
$417
Near North Side
Free Wi-Fi
Dallas/Fort Worth
Breakfast
3 nights + flight
$422
Last minute vacation packages to Chicago
Show allNear West Side
Free Wi-Fi
Pet friendly
Memphis
Breakfast
3 nights + flight
$509
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.
Everything you need to know for your vacation in Chicago
Complete your trip to Chicago
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 |