Holidays in Chicago

Holidays in Chicago

2 travellers

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Cheap Chicago package deals

These are the best prices for 8-11 May.
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BreakfastHalf boardSelf cateringAll-inclusiveMeals not included

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$280 - $547$547 - $814$814 - $1,080$1,080 - $1,348$1,348+ per night

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Free breakfastFree internetFree airport shuttleFree parking

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
8.1 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
New York LaGuardia
Meals not included
3 nights + flight
$692
River Hotel - Chicago - Lobby
River Hotel - Chicago - Lobby
River Hotel
8.4 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Raleigh-Durham
Meals not included
3 nights + flight
$485
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
7.9 Good
Near North Side
Pool
Pet-friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
$708
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
8.1 Very Good
O'Hare
Airport shuttle
Pool
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$525
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
Los Angeles
Meals not included
3 nights + flight
$613
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Denver Intl
Meals not included
3 nights + flight
$1,131
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Los Angeles
Meals not included
3 nights + flight
$848
DoubleTree by Hilton Chicago Midway Airport - Chicago - Lobby
DoubleTree by Hilton Chicago Midway Airport - Chicago - Lobby
DoubleTree by Hilton Chicago Midway Airport
8.7 Very Good
Airport shuttle
Free Wi-Fi
Pool
Cleveland Hopkins Intl
Meals not included
3 nights + flight
$549
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$536
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
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$637
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
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$614
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.2 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Denver Intl
Meals not included
3 nights + flight
$922
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk
8.4 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$512
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel
8.7 Very Good
Downtown
Pet-friendly
Spa
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$818
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.6 Very Good
Downtown
Free Wi-Fi
Denver Intl
Meals not included
3 nights + flight
$697
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.6 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Los Angeles
Meals not included
3 nights + flight
$1,131

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
Denver Intl
All-inclusive
3 nights + flight
$1,178

Last minute holiday 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
8.6 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Los Angeles
Meals not included
3 nights + flight
$614
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
Los Angeles
Meals not included
3 nights + flight
$541
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
Los Angeles
Breakfast
3 nights + flight
$608

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 $548; Family holiday $1,645; Romantic holiday $1,645; Budget holiday $2,572.

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)$548
Family holiday (Flight+Hotel)$1,645
Romantic holiday (Flight+Hotel)$1,645
Budget holiday (Flight+Hotel)$2,572