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$ 235 - C$ 420C$ 420 - C$ 607C$ 607 - C$ 794C$ 794 - C$ 980C$ 980+ 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
8.8 Very good
Near North Side
Free Wi-Fi
Pet friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 372
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
8.1 Very good
Near North Side
Pool
Pet friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 265
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Hotels Chicago Magnificent Mile By IHG
8 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 437
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
New York John F Kennedy Intl
Breakfast
3 nights + flight
C$ 354
City Suites Hotel - Chicago - Living room
City Suites Hotel - Chicago - Living room
City Suites Hotel
8 Very good
Lake View
Free Wi-Fi
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 327
Hilton Chicago - Chicago - Living room
Hilton Chicago - Chicago - Living room
Hilton Chicago
7.9 Good
Downtown
Free Wi-Fi
Pool
Pet friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 388
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.6 Very good
Near West Side
Free Wi-Fi
Pet friendly
New York John F Kennedy Intl
Breakfast
3 nights + flight
C$ 300
L7 Chicago by LOTTE - Chicago - Lounge
L7 Chicago by LOTTE - Chicago - Lounge
L7 Chicago by LOTTE
9.1 Wonderful
Downtown
Free Wi-Fi
Pet friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 399
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
C$ 568
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
Miami
Meals not included
3 nights + flight
C$ 347
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8 Very good
Downtown
Pool
Pet friendly
Spa
Miami
Meals not included
3 nights + flight
C$ 1,062
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago
9.1 Wonderful
Near North Side
Pool
Pet friendly
Spa
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
C$ 882
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.2 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
C$ 770
The Willows Hotel - Chicago - Lobby
The Willows Hotel - Chicago - Lobby
The Willows Hotel
7.9 Good
Lake View
Free Wi-Fi
New York John F Kennedy Intl
Meals not included
3 nights + flight
C$ 336
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
New York John F Kennedy Intl
Breakfast
3 nights + flight
C$ 286
Four Seasons Hotel Chicago - Chicago - Lounge
Four Seasons Hotel Chicago - Chicago - Lounge
Four Seasons Hotel Chicago
8.7 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
C$ 868

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
Phoenix Sky Harbor Intl
All inclusive
3 nights + flight
C$ 1,090

Last minute vacation packages to Chicago

Show all
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Lobby
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Lobby
The Allegro Royal Sonesta Hotel Chicago Loop
8.4 Very good
Downtown
Pet friendly
Philadelphia
Meals not included
3 nights + flight
C$ 519
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
Philadelphia
Meals not included
3 nights + flight
C$ 439

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$ 728; Family vacation C$ 660; Romantic vacation C$ 769; Luxury vacation C$ 761; Budget vacation C$ 542.

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$ 728
Family vacation (Flight+Hotel)C$ 660
Romantic vacation (Flight+Hotel)C$ 769
Luxury vacation (Flight+Hotel)C$ 761
Budget vacation (Flight+Hotel)C$ 542