Vacations in Chicago

Vacations in Chicago

2 travellers

KAYAK searches hundreds of travel sites at once for vacation package deals in Chicago

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.

Search
Best Deals
Tips
Vacation information

Cheap Chicago package deals

Discover the best prices by selecting your travel dates on KAYAK.

Most popular Chicago flight and hotel deals

Show all
Omni Chicago Hotel
8.7 Very good
Near North Side
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 617
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
4.8 Mediocre
South Side
Parking
Pet friendly
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
C$ 305
Near North Side
Free Wi-Fi
Pool
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 430
Downtown
Free Wi-Fi
Pool
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 549
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.4 Very good
Near West Side
Free Wi-Fi
Pet friendly
Los Angeles
Breakfast
3 nights + flight
C$ 533
Near North Side
Free Wi-Fi
Pet friendly
Raleigh-Durham
Meals not included
3 nights + flight
C$ 619
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$ 726
Downtown
Free Wi-Fi
Pool
Pet friendly
Raleigh-Durham
Meals not included
3 nights + flight
C$ 664
Near North Side
Free Wi-Fi
Pet friendly
Spa
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 509
Downtown
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 444
Best Motel By OYO Chicago I-90 - Chicago - Bedroom
Best Motel By OYO Chicago I-90 - Chicago - Bedroom
Best Motel By OYO Chicago I-90
1.7 Poor
South Side
Parking
Pet friendly
Knoxville McGhee Tyson
Meals not included
3 nights + flight
C$ 329
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
South Side
Free Wi-Fi
Fort Myers SW Florida Intl
Breakfast
3 nights + flight
C$ 606
Lake View
Free Wi-Fi
Fort Myers SW Florida Intl
Meals not included
3 nights + flight
C$ 488
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Los Angeles
Meals not included
3 nights + flight
C$ 1,152
The Talbott Hotel
8.6 Very good
Near North Side
Free Wi-Fi
Pet friendly
Raleigh-Durham
Meals not included
3 nights + flight
C$ 675
Downtown
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 461

Last minute vacation packages to Chicago

Show all
Near North Side
Free Wi-Fi
Pool
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
C$ 881
Near North Side
Free Wi-Fi
Pet friendly
Charlotte Douglas
Breakfast
3 nights + flight
C$ 729
L7 Chicago by LOTTE
9.1 Wonderful
Downtown
Free Wi-Fi
Pet friendly
Charlotte Douglas
Meals not included
3 nights + flight
C$ 751
Lincoln Park
Free Wi-Fi
Nashville Intl
Meals not included
3 nights + flight
C$ 516

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$ 723; Family vacation C$ 656; Romantic vacation C$ 764; Luxury vacation C$ 757; Budget vacation C$ 539.

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)C$ 723
Family vacation (Flight+Hotel)C$ 656
Romantic vacation (Flight+Hotel)C$ 764
Luxury vacation (Flight+Hotel)C$ 757
Budget vacation (Flight+Hotel)C$ 539

Chicago vacation: Search Chicago vacation packages on KAYAK. KAYAK is a travel tool that searches Chicago trips on hundreds of travel sites to help you find the Chicago package that suits you best. Discover Chicago deals now and book your Chicago flight and hotel today.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.