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.
Go to map

Search by stars

2+ stars3+ stars4+ stars5 stars

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by board

BreakfastHalf boardSelf cateringAll inclusiveMeals not included

Search by price

C$ 224 - C$ 445C$ 445 - C$ 663C$ 663 - C$ 882C$ 882 - C$ 1,103C$ 1,103+ per night

Search by freebies

Free breakfastFree internetFree airport shuttleFree parking

Most popular Chicago flight and hotel deals

Show all
Thompson Chicago - Chicago - Living room
Thompson Chicago - Chicago - Living room
Thompson Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 509
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
8 Very good
Near North Side
Pool
Pet friendly
San Diego
Meals not included
3 nights + flight
C$ 385
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lobby
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lobby
Residence Inn by Marriott Chicago Downtown Magnificent Mile
9 Wonderful
Near North Side
Free Wi-Fi
Pet friendly
San Diego
Breakfast
3 nights + flight
C$ 487
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.6 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 398
Chicago Marriott Downtown Magnificent Mile - Chicago - Bedroom
Chicago Marriott Downtown Magnificent Mile - Chicago - Bedroom
Chicago Marriott Downtown Magnificent Mile
8.5 Very good
Near North Side
San Diego
Meals not included
3 nights + flight
C$ 571
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
7.9 Good
Near North Side
Pool
Pet friendly
Orlando
Breakfast
3 nights + flight
C$ 508
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG
8.2 Very good
Near West Side
Free Wi-Fi
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 420
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
San Diego
Meals not included
3 nights + flight
C$ 465
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
San Diego
Meals not included
3 nights + flight
C$ 974
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.2 Very good
Downtown
Pool
Pet friendly
Spa
San Diego
Meals not included
3 nights + flight
C$ 945
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop
8.3 Very good
Downtown
Free Wi-Fi
Pool
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 437
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.3 Very good
Near North Side
Free Wi-Fi
Pool
Orlando
Meals not included
3 nights + flight
C$ 371
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Lounge
SpringHill Suites by Marriott Chicago Downtown/River North - Chicago - Lounge
SpringHill Suites by Marriott Chicago Downtown/River North
8.8 Very good
Near North Side
Free Wi-Fi
Orlando
Meals not included
3 nights + flight
C$ 371
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.6 Very good
Downtown
Free Wi-Fi
Orlando
Meals not included
3 nights + flight
C$ 540
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.6 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
San Diego
Meals not included
3 nights + flight
C$ 904
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago
8.6 Very good
Downtown
Free Wi-Fi
Pet friendly
Orlando
Meals not included
3 nights + flight
C$ 469

All inclusive vacation packages to Chicago

Show all
The Wheeler Mansion - Chicago - Dining room
The Wheeler Mansion - Chicago - Dining room
The Wheeler Mansion
9.8 Wonderful
Near South Side
Free Wi-Fi
San Diego
All inclusive
3 nights + flight
C$ 1,081

Last minute vacation packages to Chicago

Show all
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
8.5 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
London Heathrow
Meals not included
3 nights + flight
C$ 1,672
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
London Heathrow
Meals not included
3 nights + flight
C$ 1,687
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.7 Very good
Near West Side
Free Wi-Fi
Pet friendly
London Heathrow
Breakfast
3 nights + flight
C$ 1,686

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$ 725; Family vacation C$ 657; Romantic vacation C$ 766; Luxury vacation C$ 758; Budget vacation C$ 540.

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

Chicago vacation information

Top vacation (Flight+Hotel)C$ 725
Family vacation (Flight+Hotel)C$ 657
Romantic vacation (Flight+Hotel)C$ 766
Luxury vacation (Flight+Hotel)C$ 758
Budget vacation (Flight+Hotel)C$ 540