Holidays in Chicago

Holidays in Chicago

2 travellers

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Cheap Chicago package deals

These are the best prices for 3-6 Apr.
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BreakfastHalf boardSelf cateringAll-inclusiveMeals not included

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$333 - $570$570 - $808$808 - $1,045$1,045 - $1,284$1,284+ 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 - Living room
Thompson Chicago - Chicago - Living room
Thompson Chicago
8.9 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Newark
Meals not included
3 nights + flight
$520
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
8 Very Good
Near North Side
Pool
Pet-friendly
Newark
Meals not included
3 nights + flight
$457
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
Newark
Meals not included
3 nights + flight
$610
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.6 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Newark
Meals not included
3 nights + flight
$393
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
8.3 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Charlotte Douglas
Breakfast
3 nights + flight
$448
Hilton Chicago - Chicago - Living room
Hilton Chicago - Chicago - Living room
Hilton Chicago
7.9 Good
Downtown
Free Wi-Fi
Pool
Pet-friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
$464
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
Newark
Breakfast
3 nights + flight
$455
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
Newark
Meals not included
3 nights + flight
$446
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
Charlotte Douglas
Meals not included
3 nights + flight
$1,027
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
$501
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Newark
Meals not included
3 nights + flight
$462
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
Charlotte Douglas
Meals not included
3 nights + flight
$516
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
Los Angeles Los Angeles
Meals not included
3 nights + flight
$565
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago - Chicago - Lounge
Riu Plaza Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Charlotte Douglas
Meals not included
3 nights + flight
$509
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.6 Very Good
Downtown
Free Wi-Fi
Newark
Meals not included
3 nights + flight
$531
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
Charlotte Douglas
Meals not included
3 nights + flight
$958

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
Charlotte Douglas
All-inclusive
3 nights + flight
$1,144

Last minute holiday 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
Fort Lauderdale
Meals not included
3 nights + flight
$846
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
$671

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 $559; Family holiday $1,677; Romantic holiday $1,677; Budget holiday $2,623.

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)$559
Family holiday (Flight+Hotel)$1,677
Romantic holiday (Flight+Hotel)$1,677
Budget holiday (Flight+Hotel)$2,623