Vacations in Chicago

Vacations in Chicago

2 travelers

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$207 - $328$328 - $449$449 - $570$570 - $691$691+ 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
8.1 Very good
Near North Side
Pool
Pet friendly
Orlando
Meals not included
3 nights + flight
$292
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
Orlando
Meals not included
3 nights + flight
$403
Chic Cornelia Getaway - Chicago - Living room
Chic Cornelia Getaway - Chicago - Living room
Chic Cornelia Getaway
1 Poor
Lake View
Parking
Free Wi-Fi
Pet friendly
Orlando
Meals not included
3 nights + flight
$1,287
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
Los Angeles
Breakfast
3 nights + flight
$360
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
3.4 Poor
South Side
Parking
Pet friendly
Los Angeles
Meals not included
3 nights + flight
$232
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
Los Angeles
Breakfast
3 nights + flight
$280
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
Orlando
Breakfast
3 nights + flight
$269
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
Orlando
Breakfast
3 nights + flight
$320
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
Los Angeles
Meals not included
3 nights + flight
$334
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.2 Very good
Downtown
Pool
Pet friendly
Spa
Los Angeles
Meals not included
3 nights + flight
$690
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Los Angeles
Meals not included
3 nights + flight
$459
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Los Angeles
Meals not included
3 nights + flight
$249
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
Meals not included
3 nights + flight
$319
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
8.2 Very good
Near North Side
Free Wi-Fi
Pool
Los Angeles
Meals not included
3 nights + flight
$254
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Lobby
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
South Side
Free Wi-Fi
Los Angeles
Breakfast
3 nights + flight
$276
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Los Angeles
Breakfast
3 nights + flight
$312

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
$1,188

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