Vacations in Chicago

Vacations in Chicago

2 travelers

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Cheap Chicago package deals

These are the best prices for May 16 - 19.
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$258 - $451$451 - $644$644 - $837$837 - $1,030$1,030+ per night

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Most popular Chicago flight and hotel deals

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The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
$355
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
San Francisco
Meals not included
3 nights + flight
$437
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
Baltimore/Washington
Meals not included
3 nights + flight
$368
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
8.2 Very good
Near North Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Breakfast
3 nights + flight
$369
Hotel Versey Chicago Lincoln Park - Chicago - Lounge
Hotel Versey Chicago Lincoln Park - Chicago - Lounge
Hotel Versey Chicago Lincoln Park
8 Very good
Lake View
Free Wi-Fi
Pet friendly
San Francisco
Meals not included
3 nights + flight
$377
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
7.9 Good
Near North Side
Pool
Pet friendly
Phoenix Sky Harbor Intl
Breakfast
3 nights + flight
$462
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
$500
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
San Francisco
Meals not included
3 nights + flight
$746
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
7.8 Good
Downtown
Pool
Pet friendly
Spa
San Francisco
Meals not included
3 nights + flight
$1,041
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Baltimore/Washington
Meals not included
3 nights + flight
$347
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
Baltimore/Washington
Meals not included
3 nights + flight
$513
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.6 Very good
Downtown
Free Wi-Fi
Baltimore/Washington
Meals not included
3 nights + flight
$427
Cambria Hotel Chicago Loop - Theatre District - Chicago - Bedroom
Cambria Hotel Chicago Loop - Theatre District - Chicago - Bedroom
Cambria Hotel Chicago Loop - Theatre District
8.3 Very good
Downtown
Free Wi-Fi
San Francisco
Meals not included
3 nights + flight
$430
Hampton Inn Chicago Downtown/Magnificent Mile - Chicago - Lounge
Hampton Inn Chicago Downtown/Magnificent Mile - Chicago - Lounge
Hampton Inn Chicago Downtown/Magnificent Mile
7.5 Good
Near North Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Breakfast
3 nights + flight
$371
Freehand Chicago - Chicago - Lounge
Freehand Chicago - Chicago - Lounge
Freehand Chicago
7.1 Good
Near North Side
Free Wi-Fi
Pet friendly
San Francisco
Meals not included
3 nights + flight
$335
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.3 Good
Downtown
Free Wi-Fi
Baltimore/Washington
Meals not included
3 nights + flight
$336

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
Oklahoma City Will Rogers World
All inclusive
3 nights + flight
$926

Last minute vacation packages to Chicago

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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
3 Poor
South Side
Parking
Pet friendly
Fort Lauderdale
Meals not included
3 nights + flight
$440
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.7 Very good
Near West Side
Free Wi-Fi
Pet friendly
Fort Lauderdale
Breakfast
3 nights + flight
$847
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.3 Wonderful
Near West Side
Pool
Pet friendly
Fort Lauderdale
Breakfast
3 nights + flight
$1,010

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 $120; Family vacation $343; Romantic vacation $324; Luxury vacation $390; Budget vacation $253.

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)$120
Family vacation (Flight+Hotel)$343
Romantic vacation (Flight+Hotel)$324
Luxury vacation (Flight+Hotel)$390
Budget vacation (Flight+Hotel)$253