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

3+ 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$ 161 - C$ 315C$ 315 - C$ 470C$ 470 - C$ 624C$ 624 - C$ 778C$ 778+ 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
Miami
Meals not included
3 nights + flight
C$ 365
Le Méridien Essex Chicago - Chicago - Bedroom
Le Méridien Essex Chicago - Chicago - Bedroom
Le Méridien Essex Chicago
8.2 Very good
Downtown
Miami
Meals not included
3 nights + flight
C$ 339
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
Los Angeles
Meals not included
3 nights + flight
C$ 374
Admiral Motel By OYO Chicago I-94 - Chicago - Balcony
Admiral Motel By OYO Chicago I-94 - Chicago - Balcony
Admiral Motel By OYO Chicago I-94
3.3 Poor
South Side
Parking
Pet friendly
Miami
Meals not included
3 nights + flight
C$ 281
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
Pet friendly
Miami
Meals not included
3 nights + flight
C$ 285
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical - Chicago - Lounge
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical - Chicago - Lounge
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
7.7 Good
Near North Side
Free Wi-Fi
New York LaGuardia
Breakfast
3 nights + flight
C$ 321
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
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
C$ 334
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown
8.2 Very good
Near North Side
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
C$ 354
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
Miami
Meals not included
3 nights + flight
C$ 349
Eurostars Magnificent Mile - Chicago - Living room
Eurostars Magnificent Mile - Chicago - Living room
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Miami
Meals not included
3 nights + flight
C$ 313
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop
8.2 Very good
Downtown
Free Wi-Fi
Pool
Pet friendly
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
C$ 408
Homewood Suites by Hilton - Chicago Downtown South Loop - Chicago - Living room
Homewood Suites by Hilton - Chicago Downtown South Loop - Chicago - Living room
Homewood Suites by Hilton - Chicago Downtown South Loop
8 Very good
Downtown
Free Wi-Fi
Pool
Miami
Breakfast
3 nights + flight
C$ 284
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
8.3 Very good
Downtown
Pet friendly
Miami
Meals not included
3 nights + flight
C$ 306
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bedroom
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bedroom
La Quinta Inn & Suites by Wyndham Chicago Downtown
7.9 Good
Downtown
Free Wi-Fi
Pet friendly
Spa
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
C$ 367
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
Los Angeles
Meals not included
3 nights + flight
C$ 500
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bar
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bar
Hilton Garden Inn Chicago Downtown Riverwalk
8.4 Very good
Downtown
Free Wi-Fi
Pet friendly
New York LaGuardia
Meals not included
3 nights + flight
C$ 365

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
Los Angeles
All inclusive
3 nights + flight
C$ 946

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$ 730; Family vacation C$ 662; Romantic vacation C$ 771; Luxury vacation C$ 763; Budget vacation C$ 544.

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$ 730
Family vacation (Flight+Hotel)C$ 662
Romantic vacation (Flight+Hotel)C$ 771
Luxury vacation (Flight+Hotel)C$ 763
Budget vacation (Flight+Hotel)C$ 544