Vacations in Chicago

Vacations in Chicago

2 travelers

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$202 - $441$441 - $680$680 - $919$919 - $1,159$1,159+ 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
7.9 Good
Near North Side
Pool
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
$382
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel
8.9 Very good
Near North Side
Free Wi-Fi
Pet friendly
Philadelphia
Meals not included
3 nights + flight
$589
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
Philadelphia
Meals not included
3 nights + flight
$496
Chicago Marriott Downtown Magnificent Mile - Chicago - Building
Chicago Marriott Downtown Magnificent Mile - Chicago - Building
Chicago Marriott Downtown Magnificent Mile
8.3 Very good
Near North Side
Tampa
Meals not included
3 nights + flight
$552
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.4 Very good
Loop
Free Wi-Fi
Pet friendly
Washington, D.C. Dulles Intl
Meals not included
3 nights + flight
$342
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
Philadelphia
Meals not included
3 nights + flight
$467
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$742
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.3 Wonderful
Near West Side
Pool
Pet friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
$468
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Baltimore/Washington
Meals not included
3 nights + flight
$443
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
Loop
Pet friendly
Baltimore/Washington
Meals not included
3 nights + flight
$460
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.3 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Tampa
Meals not included
3 nights + flight
$818
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.1 Very good
Near North Side
Free Wi-Fi
Pool
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$434
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
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$491
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.3 Very good
Loop
Free Wi-Fi
Baltimore/Washington
Meals not included
3 nights + flight
$446
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.9 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$1,017
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago
8.6 Very good
Loop
Free Wi-Fi
Pet friendly
Newark
Meals not included
3 nights + flight
$518

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
Baltimore/Washington
All inclusive
3 nights + flight
$788

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
Newark
Meals not included
3 nights + flight
$594
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 LaGuardia
Meals not included
3 nights + flight
$836
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.8 Very good
Near West Side
Free Wi-Fi
Pet friendly
Newark
Breakfast
3 nights + flight
$550

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 $106; Family vacation $279; Romantic vacation $324; Luxury vacation $407; Budget vacation $251.

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)$106
Family vacation (Flight+Hotel)$279
Romantic vacation (Flight+Hotel)$324
Luxury vacation (Flight+Hotel)$407
Budget vacation (Flight+Hotel)$251