Vacations in Chicago

Vacations in Chicago

2 travelers

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Cheap Chicago package deals

These are the best prices for Jul 26 - 29.
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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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$240 - $499$499 - $759$759 - $1,019$1,019 - $1,279$1,279+ per night

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Most popular Chicago flight and hotel deals

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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
8.1 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Philadelphia
Meals not included
3 nights + flight
$491
The Chicago Hotel Collection Ambassador Gold Coast - Chicago - Lounge
The Chicago Hotel Collection Ambassador Gold Coast - Chicago - Lounge
The Chicago Hotel Collection Ambassador Gold Coast
8.1 Very good
Near North Side
Philadelphia
Meals not included
3 nights + flight
$403
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.8 Very good
Near West Side
Free Wi-Fi
Pet friendly
Philadelphia
Breakfast
3 nights + flight
$341
Palmer House a Hilton Hotel - Chicago - Lounge
Palmer House a Hilton Hotel - Chicago - Lounge
Palmer House a Hilton Hotel
8 Very good
Downtown
Free Wi-Fi
Pool
Pet friendly
Spa
Philadelphia
Meals not included
3 nights + flight
$404
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection
7.9 Good
Near North Side
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$286
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Philadelphia
Meals not included
3 nights + flight
$394
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
Los Angeles
Meals not included
3 nights + flight
$912
Ivy Boutique Hotel - Chicago - Bathroom
Ivy Boutique Hotel - Chicago - Bathroom
Ivy Boutique Hotel
8.4 Very good
Near North Side
Free Wi-Fi
Philadelphia
Meals not included
3 nights + flight
$384
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.3 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Los Angeles
Meals not included
3 nights + flight
$761
Best Western River North Hotel - Chicago - Balcony
Best Western River North Hotel - Chicago - Balcony
Best Western River North Hotel
7.3 Good
Near North Side
Free Wi-Fi
Pool
Philadelphia
Meals not included
3 nights + flight
$339
The Drake - Chicago - Lobby
The Drake - Chicago - Lobby
The Drake
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Los Angeles
Meals not included
3 nights + flight
$493
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Philadelphia
Meals not included
3 nights + flight
$896
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
Los Angeles
Meals not included
3 nights + flight
$565
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel
8.1 Very good
Downtown
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$311
Sofitel Chicago Magnificent Mile - Chicago - Gym
Sofitel Chicago Magnificent Mile - Chicago - Gym
Sofitel Chicago Magnificent Mile
8.8 Very good
Near North Side
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$581
Club Quarters Hotel Central Loop, Chicago - Chicago - Lobby
Club Quarters Hotel Central Loop, Chicago - Chicago - Lobby
Club Quarters Hotel Central Loop, Chicago
8.2 Very good
Downtown
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$310

All inclusive vacation packages to Chicago

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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
$870

Last minute vacation packages to Chicago

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The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
7.9 Good
Downtown
Pool
Pet friendly
Spa
Jackson-Evers Intl
Meals not included
3 nights + flight
$1,909
Urban Chicago Oasis - Chicago - Living room
Urban Chicago Oasis - Chicago - Living room
Urban Chicago Oasis
1 Poor
Lake View
Baltimore/Washington
Meals not included
3 nights + flight
$1,391
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
2.8 Poor
South Side
Parking
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
$488
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
Baltimore/Washington
Breakfast
3 nights + flight
$885

When to book a vacation in Chicago

Price includes flights and 3 nights accommodation for 2 travelers. 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 travelers: Top vacation $111; Family vacation $308; Romantic vacation $324; Luxury vacation $390; Budget vacation $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)$111
Family vacation (Flight+Hotel)$308
Romantic vacation (Flight+Hotel)$324
Luxury vacation (Flight+Hotel)$390
Budget vacation (Flight+Hotel)$256