Vacations in Chicago
2 travellers
KAYAK searches hundreds of travel sites at once for vacation package deals in Chicago
...and more
Here is why travelers choose KAYAK
Free to useThere are no hidden charges or fees.
Filter your dealsFilter by free cancellation, free breakfast and more.
Millions of reviewsCheck ratings based on millions of real guest reviews.
Bundle and saveSave money when you bundle your flight + hotel.
Cheap Chicago package deals
Discover the best prices by selecting your travel dates on KAYAK.
Most popular Chicago flight and hotel deals
Show allNear North Side
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 451
Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom![Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom]()
Admiral Motel By OYO Chicago I-94
South Side
Parking
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 310
Near North Side
Free Wi-Fi
Pet friendly
Los Angeles
Breakfast
3 nights + flight
C$ 473
Downtown
Free Wi-Fi
Pool
Pet friendly
Philadelphia
Meals not included
3 nights + flight
C$ 533
Downtown
Pet friendly
Los Angeles
Breakfast
3 nights + flight
C$ 435
Near North Side
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
C$ 556
Near North Side
Free Wi-Fi
Pool
Pet friendly
Austin Bergstrom
Meals not included
3 nights + flight
C$ 793
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Los Angeles
Meals not included
3 nights + flight
C$ 856
Hampton Inn & Suites Chicago Medical District UIC - Chicago - Bedroom![Hampton Inn & Suites Chicago Medical District UIC - Chicago - Bedroom]()
Hampton Inn & Suites Chicago Medical District UIC
Near West Side
Pool
Pet friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
C$ 630
The Royal Sonesta Chicago River North - Chicago - Lounge![The Royal Sonesta Chicago River North - Chicago - Lounge]()
The Royal Sonesta Chicago River North
Near North Side
Free Wi-Fi
Pool
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 486
The St. Regis Chicago - Chicago - Restaurant![The St. Regis Chicago - Chicago - Restaurant]()
The St. Regis Chicago
Downtown
Pool
Pet friendly
Spa
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 1,119
Downtown
Free Wi-Fi
Pet friendly
Spa
Philadelphia
Meals not included
3 nights + flight
C$ 495
The Neighborhood Hotel Little Italy - Chicago - Living room![The Neighborhood Hotel Little Italy - Chicago - Living room]()
The Neighborhood Hotel Little Italy
Near West Side
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 691
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room![The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room]()
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 552
Near North Side
Free Wi-Fi
Pool
Los Angeles
Meals not included
3 nights + flight
C$ 366
Near North Side
Free Wi-Fi
Los Angeles
Breakfast
3 nights + flight
C$ 462
Last minute vacation packages to Chicago
Show allHyatt House Chicago Medical/University District - Chicago - Building![Hyatt House Chicago Medical/University District - Chicago - Building]()
Hyatt House Chicago Medical/University District
Near West Side
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Breakfast
3 nights + flight
C$ 653
When to book a vacation in Chicago
Price includes flights and 3 nights accommodation for 2 travellers. 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 travellers: Top vacation C$ 721; Family vacation C$ 654; Romantic vacation C$ 762; Luxury vacation C$ 755; Budget vacation C$ 537.
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) | C$ 721 |
|---|---|
| Family vacation (Flight+Hotel) | C$ 654 |
| Romantic vacation (Flight+Hotel) | C$ 762 |
| Luxury vacation (Flight+Hotel) | C$ 755 |
| Budget vacation (Flight+Hotel) | C$ 537 |