Vacations in Chicago

Vacations in Chicago

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Cheap Chicago package deals

These are the best prices for Apr 5 - 8.
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$214 - $402$402 - $589$589 - $777$777 - $965$965+ per night

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Most popular Chicago flight and hotel deals

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Thompson Chicago - Chicago - Living room
Thompson Chicago - Chicago - Living room
Thompson Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
$436
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
$370
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
Los Angeles Los Angeles
Meals not included
3 nights + flight
$426
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel
8.8 Very good
Near North Side
Free Wi-Fi
Pet friendly
Los Angeles Los Angeles
Meals not included
3 nights + flight
$433
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
Los Angeles Los Angeles
Meals not included
3 nights + flight
$366
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
8.3 Very good
Near North Side
Free Wi-Fi
Pet friendly
Newark
Meals not included
3 nights + flight
$372
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
Los Angeles Los Angeles
Breakfast
3 nights + flight
$379
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
Los Angeles Los Angeles
Meals not included
3 nights + flight
$388
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
Newark
Meals not included
3 nights + flight
$351
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
8.5 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Newark
Meals not included
3 nights + flight
$404
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop
8.9 Very good
Downtown
Free Wi-Fi
Pet friendly
Spa
Los Angeles Los Angeles
Meals not included
3 nights + flight
$410
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Newark
Meals not included
3 nights + flight
$371
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
Downtown
Pet friendly
Los Angeles Los Angeles
Meals not included
3 nights + flight
$366
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
Newark
Meals not included
3 nights + flight
$703
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago
8.2 Very good
Near North Side
Pet friendly
Spa
Newark
Meals not included
3 nights + flight
$341
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.6 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$853

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
Atlanta Hartsfield-Jackson
All inclusive
3 nights + flight
$1,090

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 $115; Family vacation $268; Romantic vacation $324; Luxury vacation $390; Budget vacation $289.

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)$115
Family vacation (Flight+Hotel)$268
Romantic vacation (Flight+Hotel)$324
Luxury vacation (Flight+Hotel)$390
Budget vacation (Flight+Hotel)$289