Holidays in Chicago

Holidays in Chicago

2 travellers

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Cheap Chicago package deals

These are the best prices for 30 Jul - 2 Aug.
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BreakfastHalf boardSelf cateringAll-inclusiveMeals not included

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$447 - $724$724 - $1,003$1,003 - $1,281$1,281 - $1,558$1,558+ per night

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Free breakfastFree internetFree airport shuttleFree parking

Most popular Chicago flight and hotel deals

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Thompson Chicago - Chicago - Lobby
Thompson Chicago - Chicago - Lobby
Thompson Chicago
8.9 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Salt Lake City
Meals not included
3 nights + flight
$806
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
8.1 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$726
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
Houston George Bush Intcntl
Meals not included
3 nights + flight
$701
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.4 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$675
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
Houston George Bush Intcntl
Breakfast
3 nights + flight
$583
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Salt Lake City
Meals not included
3 nights + flight
$1,023
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
Houston George Bush Intcntl
Meals not included
3 nights + flight
$641
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
$618
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
Los Angeles
Meals not included
3 nights + flight
$1,141
DoubleTree by Hilton Hotel Chicago - Magnificent Mile - Chicago - Lounge
DoubleTree by Hilton Hotel Chicago - Magnificent Mile - Chicago - Lounge
DoubleTree by Hilton Hotel Chicago - Magnificent Mile
8.1 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Salt Lake City
Meals not included
3 nights + flight
$747
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.4 Very Good
Downtown
Free Wi-Fi
Los Angeles
Meals not included
3 nights + flight
$827
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago
8.6 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Newark
Meals not included
3 nights + flight
$825
Sofitel Chicago Magnificent Mile - Chicago - Gym
Sofitel Chicago Magnificent Mile - Chicago - Gym
Sofitel Chicago Magnificent Mile
8.8 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
$878
Hampton Inn Chicago Downtown/Magnificent Mile - Chicago - Lounge
Hampton Inn Chicago Downtown/Magnificent Mile - Chicago - Lounge
Hampton Inn Chicago Downtown/Magnificent Mile
7.5 Good
Near North Side
Free Wi-Fi
Pet-friendly
Houston George Bush Intcntl
Breakfast
3 nights + flight
$777
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection
8.5 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
$794
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.2 Good
Downtown
Free Wi-Fi
Salt Lake City
Meals not included
3 nights + flight
$681

All inclusive holiday 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
Phoenix Sky Harbor Intl
All-inclusive
3 nights + flight
$1,306

Last minute holiday packages to Chicago

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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
San Diego
Meals not included
3 nights + flight
$1,047
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Building
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Building
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.3 Very Good
Near North Side
Free Wi-Fi
Pool
Dallas/Fort Worth
Meals not included
3 nights + flight
$1,163

When to book a holiday in Chicago

Price includes flights and 3 nights accommodation for 2 travellers. Prices are not fixed and may vary with time.

Tips for finding Chicago package deals

  • There are loads of types of holidays 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 travellers: Top holiday $262; Family holiday $1,702; Romantic holiday $787; Luxury holiday $758; Budget holiday $787.

Where to stay in Chicago

Our map will help you find the perfect place to stay for your holiday in Chicago by showing you the exact location of each hotel.

Everything you need to know for your holiday in Chicago

Chicago holiday information

Top holiday (Flight+Hotel)$262
Family holiday (Flight+Hotel)$1,702
Romantic holiday (Flight+Hotel)$787
Luxury holiday (Flight+Hotel)$758
Budget holiday (Flight+Hotel)$787