Vacations in Chicago

Vacations in Chicago

2 travelers

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$193 - $349$349 - $506$506 - $663$663 - $819$819+ per night

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Most popular Chicago flight and hotel deals

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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
Fort Lauderdale
Meals not included
3 nights + flight
$351
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
8.9 Very good
Near North Side
Free Wi-Fi
Pet friendly
Orlando
Breakfast
3 nights + flight
$333
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
Fort Lauderdale
Meals not included
3 nights + flight
$384
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
Pet friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
$230
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
New York John F Kennedy Intl
Breakfast
3 nights + flight
$247
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
Orlando
Meals not included
3 nights + flight
$304
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
Orlando
Meals not included
3 nights + flight
$324
DoubleTree by Hilton Chicago Midway Airport - Chicago - Lobby
DoubleTree by Hilton Chicago Midway Airport - Chicago - Lobby
DoubleTree by Hilton Chicago Midway Airport
8.6 Very good
Airport shuttle
Free Wi-Fi
Pool
Fort Lauderdale
Meals not included
3 nights + flight
$330
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
New York John F Kennedy Intl
Meals not included
3 nights + flight
$401
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
Orlando
Meals not included
3 nights + flight
$274
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop
8.3 Very good
Downtown
Free Wi-Fi
Pool
Pet friendly
Orlando
Meals not included
3 nights + flight
$300
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
Fort Lauderdale
Meals not included
3 nights + flight
$311
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
Fort Lauderdale
Meals not included
3 nights + flight
$193
The Hoxton, Chicago - Chicago - Lounge
The Hoxton, Chicago - Chicago - Lounge
The Hoxton, Chicago
8.3 Very good
Near West Side
Free Wi-Fi
Pool
Pet friendly
New York John F Kennedy Intl
Meals not included
3 nights + flight
$458
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Fort Lauderdale
Breakfast
3 nights + flight
$311
Central Loop Hotel - Chicago - Front desk
Central Loop Hotel - Chicago - Front desk
Central Loop Hotel
8 Very good
Downtown
Free Wi-Fi
Pet friendly
Fort Lauderdale
Meals not included
3 nights + flight
$232

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
San Juan Luis Munoz Marin Intl
All inclusive
3 nights + flight
$840

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