Vacations in Chicago

Vacations in Chicago

2 travelers

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$114 - $285$285 - $455$455 - $625$625 - $796$796+ per night

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Most popular Chicago flight and hotel deals

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Le Méridien Essex Chicago - Chicago - Bedroom
Le Méridien Essex Chicago - Chicago - Bedroom
Le Méridien Essex Chicago
8.2 Very good
Downtown
Raleigh-Durham
Meals not included
3 nights + flight
$210
Thompson Chicago - Chicago - Living room
Thompson Chicago - Chicago - Living room
Thompson Chicago
8.8 Very good
Near North Side
Free Wi-Fi
Pet friendly
Raleigh-Durham
Meals not included
3 nights + flight
$298
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
Raleigh-Durham
Meals not included
3 nights + flight
$358
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lobby
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lobby
Residence Inn by Marriott Chicago Downtown Magnificent Mile
9 Wonderful
Near North Side
Free Wi-Fi
Pet friendly
Raleigh-Durham
Breakfast
3 nights + flight
$296
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
Raleigh-Durham
Meals not included
3 nights + flight
$336
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
Raleigh-Durham
Breakfast
3 nights + flight
$240
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.6 Very good
Near West Side
Free Wi-Fi
Pet friendly
Raleigh-Durham
Breakfast
3 nights + flight
$267
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
8 Very good
Near North Side
Pool
Pet friendly
Raleigh-Durham
Breakfast
3 nights + flight
$269
Hampton Inn Majestic Chicago Theatre District - Chicago - Building
Hampton Inn Majestic Chicago Theatre District - Chicago - Building
Hampton Inn Majestic Chicago Theatre District
8.3 Very good
Downtown
Pet friendly
Raleigh-Durham
Breakfast
3 nights + flight
$234
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
Raleigh-Durham
Meals not included
3 nights + flight
$288
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Raleigh-Durham
Meals not included
3 nights + flight
$410
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop
9 Wonderful
Downtown
Free Wi-Fi
Pet friendly
Spa
Raleigh-Durham
Meals not included
3 nights + flight
$282
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
Raleigh-Durham
Meals not included
3 nights + flight
$222
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Raleigh-Durham
Meals not included
3 nights + flight
$529
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
Raleigh-Durham
Meals not included
3 nights + flight
$256
Four Seasons Hotel Chicago - Chicago - Lounge
Four Seasons Hotel Chicago - Chicago - Lounge
Four Seasons Hotel Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pool
Spa
San Francisco
Meals not included
3 nights + flight
$728

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
Raleigh-Durham
All inclusive
3 nights + flight
$951

Last minute vacation packages to Chicago

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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
Cancun
Meals not included
3 nights + flight
$572
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Cancun
Meals not included
3 nights + flight
$610
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.3 Very good
Near North Side
Free Wi-Fi
Pool
Cancun
Meals not included
3 nights + flight
$539

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 $312; Family vacation $302; Romantic vacation $332; Luxury vacation $320; Budget vacation $237.

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)$312
Family vacation (Flight+Hotel)$302
Romantic vacation (Flight+Hotel)$332
Luxury vacation (Flight+Hotel)$320
Budget vacation (Flight+Hotel)$237