Vacations in Chicago

Vacations in Chicago

2 travelers

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$168 - $302$302 - $436$436 - $570$570 - $703$703+ 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
8.8 Very good
Near North Side
Free Wi-Fi
Pet friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$274
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
8.1 Very good
Near North Side
Pool
Pet friendly
Austin Bergstrom
Meals not included
3 nights + flight
$235
The Blackstone Autograph Collection - Chicago - Lobby
The Blackstone Autograph Collection - Chicago - Lobby
The Blackstone Autograph Collection
8.7 Very good
Downtown
Pet friendly
Spa
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$252
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
Houston George Bush Intcntl
Breakfast
3 nights + flight
$299
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
7.7 Good
Near North Side
Free Wi-Fi
Houston George Bush Intcntl
Breakfast
3 nights + flight
$244
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
Baltimore/Washington
Breakfast
3 nights + flight
$205
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
Houston George Bush Intcntl
Meals not included
3 nights + flight
$231
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
Baltimore/Washington
Meals not included
3 nights + flight
$287
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
Baltimore/Washington
Breakfast
3 nights + flight
$232
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
Baltimore/Washington
Meals not included
3 nights + flight
$287
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
Baltimore/Washington
Meals not included
3 nights + flight
$798
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Baltimore/Washington
Meals not included
3 nights + flight
$357
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
Austin Bergstrom
Meals not included
3 nights + flight
$285
Chicago Marriott Ohare - Chicago - Building
Chicago Marriott Ohare - Chicago - Building
Chicago Marriott Ohare
7.6 Good
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Houston George Bush Intcntl
Meals not included
3 nights + flight
$326
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
Baltimore/Washington
Breakfast
3 nights + flight
$233
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Newark
Breakfast
3 nights + flight
$277

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
Richmond Byrd Intl
All inclusive
3 nights + flight
$847

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