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$ 274 - C$ 614C$ 614 - C$ 953C$ 953 - C$ 1,293C$ 1,293 - C$ 1,632C$ 1,632+ 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
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 455
Home2 Suites by Hilton Chicago River North - Chicago - Bedroom
Home2 Suites by Hilton Chicago River North - Chicago - Bedroom
Home2 Suites by Hilton Chicago River North
7.8 Good
Near North Side
Free Wi-Fi
Pet friendly
Nashville Intl
Breakfast
3 nights + flight
C$ 533
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
Charlotte Douglas
Meals not included
3 nights + flight
C$ 474
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
Charlotte Douglas
Meals not included
3 nights + flight
C$ 614
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
Nashville Intl
Meals not included
3 nights + flight
C$ 497
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Charlotte Douglas
Meals not included
3 nights + flight
C$ 964
Silversmith Hotel Chicago Central Loop, Tapestry Collection by Hilton - Chicago - Restaurant
Silversmith Hotel Chicago Central Loop, Tapestry Collection by Hilton - Chicago - Restaurant
Silversmith Hotel Chicago Central Loop, Tapestry Collection by Hilton
8.7 Very good
Loop
Free Wi-Fi
Charlotte Douglas
Meals not included
3 nights + flight
C$ 674
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection
7.8 Good
Near North Side
Free Wi-Fi
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
C$ 388
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Nashville Intl
Meals not included
3 nights + flight
C$ 547
Waldorf Astoria Chicago - Chicago - Bar
Waldorf Astoria Chicago - Chicago - Bar
Waldorf Astoria Chicago
9.2 Wonderful
Near North Side
Pool
Pet friendly
Spa
Charlotte Douglas
Meals not included
3 nights + flight
C$ 1,693
Ivy Boutique Hotel - Chicago - Banquet hall
Ivy Boutique Hotel - Chicago - Banquet hall
Ivy Boutique Hotel
8.3 Very good
Near North Side
Free Wi-Fi
Nashville Intl
Meals not included
3 nights + flight
C$ 560
The Drake - Chicago - Lobby
The Drake - Chicago - Lobby
The Drake
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Nashville Intl
Meals not included
3 nights + flight
C$ 630
Holiday Inn & Suites Chicago-Downtown By IHG - Chicago - Lobby
Holiday Inn & Suites Chicago-Downtown By IHG - Chicago - Lobby
Holiday Inn & Suites Chicago-Downtown By IHG
7.6 Good
Near West Side
Free Wi-Fi
Pool
Charlotte Douglas
Meals not included
3 nights + flight
C$ 548
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
Nashville Intl
Meals not included
3 nights + flight
C$ 1,560
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel
8.1 Very good
Loop
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 486
Hyatt Place Chicago Medical/University District - Chicago - Building
Hyatt Place Chicago Medical/University District - Chicago - Building
Hyatt Place Chicago Medical/University District
8.8 Very good
Near West Side
Free Wi-Fi
Pet friendly
Charlotte Douglas
Breakfast
3 nights + flight
C$ 543

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
Fort Lauderdale
All inclusive
3 nights + flight
C$ 1,068

Last minute vacation packages to Chicago

Show all
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
Newark
Meals not included
3 nights + flight
C$ 763
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
White Plains Westchester County
Breakfast
3 nights + flight
C$ 1,615
Wrigleyville Suites - Chicago - Living room
Wrigleyville Suites - Chicago - Living room
Wrigleyville Suites
7.8 Good
Wrigleyville
Free Wi-Fi
Newark
Meals not included
3 nights + flight
C$ 1,472

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$ 245; Luxury vacation C$ 487; Budget vacation C$ 255.

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$ 245
Luxury vacation (Flight+Hotel)C$ 487
Budget vacation (Flight+Hotel)C$ 255