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

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$ 388 - C$ 657C$ 657 - C$ 925C$ 925 - C$ 1,194C$ 1,194 - C$ 1,462C$ 1,462+ per night

Search by freebies

Free breakfastFree internetFree airport shuttleFree parking

Most popular Chicago flight and hotel deals

Show all
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 431
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel - Chicago - Restaurant
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel - Chicago - Restaurant
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
8 Very good
Loop
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 446
Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94
2.6 Poor
Chatham
Parking
Pet friendly
Philadelphia
Meals not included
3 nights + flight
C$ 395
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.5 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 540
Hotel Versey Chicago Lincoln Park - Chicago - Lounge
Hotel Versey Chicago Lincoln Park - Chicago - Lounge
Hotel Versey Chicago Lincoln Park
7.8 Good
Lake View
Free Wi-Fi
Pet friendly
Fort Lauderdale
Meals not included
3 nights + flight
C$ 587
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
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 550
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 879
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 503
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
Loop
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 547
The Langham Chicago - Chicago - Lounge
The Langham Chicago - Chicago - Lounge
The Langham Chicago
9.4 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 1,278
Hotel Chicago West Loop, SureStay Collection by Best Western - Chicago - Living room
Hotel Chicago West Loop, SureStay Collection by Best Western - Chicago - Living room
Hotel Chicago West Loop, SureStay Collection by Best Western
7.5 Good
Near West Side
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 501
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
2 Poor
Woodlawn
Parking
Pet friendly
Philadelphia
Meals not included
3 nights + flight
C$ 395
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare
7.7 Good
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Philadelphia
Meals not included
3 nights + flight
C$ 661
The Drake - Chicago - Lobby
The Drake - Chicago - Lobby
The Drake
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 559
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.8 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
San Francisco
Meals not included
3 nights + flight
C$ 1,311
Freehand Chicago - Chicago - Lounge
Freehand Chicago - Chicago - Lounge
Freehand Chicago
6.9 Okay
Near North Side
Free Wi-Fi
Pet friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
C$ 466

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
Dallas/Fort Worth
All inclusive
3 nights + flight
C$ 1,302

Last minute vacation packages to Chicago

Show all
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.1 Very good
Loop
Pool
Pet friendly
Spa
Salt Lake City
Meals not included
3 nights + flight
C$ 4,285
Chicago Avenue Inn - Chicago - Bathroom
Chicago Avenue Inn - Chicago - Bathroom
Chicago Avenue Inn
5.7 Fair
Humboldt Park
Parking
Free Wi-Fi
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
C$ 938
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.3 Wonderful
Near West Side
Pool
Pet friendly
Phoenix Sky Harbor Intl
Breakfast
3 nights + flight
C$ 1,744
Wrigleyville Suites - Chicago - Living room
Wrigleyville Suites - Chicago - Living room
Wrigleyville Suites
7.8 Good
Wrigleyville
Free Wi-Fi
Salt Lake City
Meals not included
3 nights + flight
C$ 1,099

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$ 86; Family vacation C$ 205; Romantic vacation C$ 246; Luxury vacation C$ 488; Budget vacation C$ 256.

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$ 86
Family vacation (Flight+Hotel)C$ 205
Romantic vacation (Flight+Hotel)C$ 246
Luxury vacation (Flight+Hotel)C$ 488
Budget vacation (Flight+Hotel)C$ 256