Vacations in Chicago
2 travelers
Wed 5/29
Sat 6/1
Search hundreds of travel sites at once for vacation package deals in Chicago
...and more
Let KAYAK do the searching
Cheap Chicago package deals
Most popular Chicago flight and hotel deals
Show allDowntown
Free Wi-Fi
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$337
Downtown
Free Wi-Fi
Miami
Meals not included
3 nights + flight
$361
Downtown
Free Wi-Fi
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$341
Downtown
Pool
Pet friendly
Denver Intl
Breakfast
3 nights + flight
$363
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Austin Bergstrom
Meals not included
3 nights + flight
$621
Downtown
Free Wi-Fi
Pool
Pet friendly
Denver Intl
Breakfast
3 nights + flight
$421
Downtown
Free Wi-Fi
Pool
Pet friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$410
Downtown
Free Wi-Fi
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$248
Downtown
Free Wi-Fi
Minneapolis St Paul
Meals not included
3 nights + flight
$349
Downtown
Pet friendly
Denver Intl
Meals not included
3 nights + flight
$299
Downtown
Free Wi-Fi
Pet friendly
Spa
Minneapolis St Paul
Meals not included
3 nights + flight
$325
Sonder The Burnham - Chicago - Bedroom![Sonder The Burnham - Chicago - Bedroom]()
Sonder The Burnham
Downtown
Free Wi-Fi
Denver Intl
Meals not included
3 nights + flight
$326
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Charlotte Douglas
Meals not included
3 nights + flight
$602
Downtown
Free Wi-Fi
Pet friendly
Charlotte Douglas
Meals not included
3 nights + flight
$384
Last minute vacation packages to Chicago
Show allThe St. Regis Chicago - Chicago - Bedroom![The St. Regis Chicago - Chicago - Bedroom]()
The St. Regis Chicago
Downtown
Pool
Pet friendly
Spa
Miami
Meals not included
3 nights + flight
$1,424
Fairmont Chicago at Millennium Park Gold Experience - Chicago - Building![Fairmont Chicago at Millennium Park Gold Experience - Chicago - Building]()
Fairmont Chicago at Millennium Park Gold Experience
Downtown
Free Wi-Fi
Pet friendly
New York LaGuardia
Breakfast
3 nights + flight
$1,140
Downtown
Free Wi-Fi
Pet friendly
Miami
Breakfast
3 nights + flight
$718
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 |
Other popular package vacation destinations
- Costa Rica package vacations
- Fort Lauderdale package vacations
- Hawaii package vacations
- Honolulu package vacations
- Kahului package vacations
- Key West package vacations
- Las Vegas package vacations
- London package vacations
- Los Angeles package vacations
- Miami package vacations
- Miami Beach package vacations
- Montego Bay package vacations
- Myrtle Beach package vacations
- Nassau package vacations
- Paris package vacations
- Playa del Carmen package vacations
- Puerto Rico package vacations
- Punta Cana package vacations
- Rome package vacations
- Saint Martin package vacations