Vacations in Chicago

Vacations in Chicago

2 travelers

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Cheap Chicago package deals

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$186 - $428$428 - $669$669 - $911$911 - $1,152$1,152+ 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
Ontario
Meals not included
3 nights + flight
$353
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG
8.1 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Spa
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$432
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 Very good
Near North Side
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Breakfast
3 nights + flight
$308
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 Very good
Near West Side
Free Wi-Fi
Pet friendly
Ontario
Meals not included
3 nights + flight
$354
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
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$395
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
$870
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
Fort Lauderdale
Breakfast
3 nights + flight
$471
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton
8.9 Very good
Loop
Free Wi-Fi
Spa
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$429
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
8.6 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$387
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very good
Near North Side
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$392
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bar
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bar
La Quinta Inn & Suites by Wyndham Chicago Downtown
8.1 Very good
Loop
Free Wi-Fi
Pet friendly
Spa
Ontario
Breakfast
3 nights + flight
$392
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
Ontario
Meals not included
3 nights + flight
$367
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
Ontario
Meals not included
3 nights + flight
$608
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
8.2 Very good
Near North Side
Free Wi-Fi
Pool
Ontario
Meals not included
3 nights + flight
$408
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel
8.5 Very good
Loop
Pet friendly
Spa
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$442
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
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$395

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 Los Angeles
All inclusive
3 nights + flight
$843

Last minute vacation packages to Chicago

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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 Los Angeles
Meals not included
3 nights + flight
$709
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
Los Angeles Los Angeles
Breakfast
3 nights + flight
$493

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