Holidays in Chicago

Holidays in Chicago

2 travellers

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Cheap Chicago package deals

These are the best prices for 12-15 Apr.
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BreakfastHalf boardSelf cateringAll-inclusiveMeals not included

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$305 - $572$572 - $838$838 - $1,106$1,106 - $1,374$1,374+ per night

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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
Baltimore/Washington
Meals not included
3 nights + flight
$620
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet-friendly
Boston Logan Intl
Meals not included
3 nights + flight
$527
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
Los Angeles Los Angeles
Meals not included
3 nights + flight
$607
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel
8.8 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Los Angeles Los Angeles
Meals not included
3 nights + flight
$616
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
Los Angeles Los Angeles
Meals not included
3 nights + flight
$521
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
Newark
Meals not included
3 nights + flight
$529
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 Los Angeles
Breakfast
3 nights + flight
$539
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
8.2 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Los Angeles Los Angeles
Meals not included
3 nights + flight
$552
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
$499
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
$575
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop
8.9 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Spa
Los Angeles Los Angeles
Meals not included
3 nights + flight
$584
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
$527
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
Los Angeles Los Angeles
Meals not included
3 nights + flight
$520
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
Newark
Meals not included
3 nights + flight
$1,000
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
Newark
Meals not included
3 nights + flight
$485
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
Baltimore/Washington
Meals not included
3 nights + flight
$1,214

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
Atlanta Hartsfield-Jackson
All-inclusive
3 nights + flight
$1,552

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 $560; Family holiday $1,679; Romantic holiday $1,679; Budget holiday $2,626.

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)$560
Family holiday (Flight+Hotel)$1,679
Romantic holiday (Flight+Hotel)$1,679
Budget holiday (Flight+Hotel)$2,626