Holidays in Chicago

Holidays in Chicago

2 travellers

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Cheap Chicago package deals

These are the best prices for 13-16 May.
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BreakfastHalf boardSelf cateringAll-inclusiveMeals not included

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$323 - $613$613 - $905$905 - $1,195$1,195 - $1,487$1,487+ 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
Newark
Meals not included
3 nights + flight
$603
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet-friendly
Newark
Meals not included
3 nights + flight
$528
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel
8.9 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Newark
Meals not included
3 nights + flight
$708
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
$544
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
8.2 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Newark
Breakfast
3 nights + flight
$511
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
Newark
Meals not included
3 nights + flight
$562
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
$596
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
Raleigh-Durham
Meals not included
3 nights + flight
$1,232
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
Newark
Meals not included
3 nights + flight
$562
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
$482
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop
8.8 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Tampa
Breakfast
3 nights + flight
$660
Hampton Inn Chicago Downtown/N Loop/Michigan Ave - Chicago - Lobby
Hampton Inn Chicago Downtown/N Loop/Michigan Ave - Chicago - Lobby
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
7.9 Good
Downtown
Free Wi-Fi
Pet-friendly
Newark
Breakfast
3 nights + flight
$527
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
Raleigh-Durham
Meals not included
3 nights + flight
$1,030
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
$577
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
$660
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
Tampa
Meals not included
3 nights + flight
$592

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
Lambert-St Louis
All-inclusive
3 nights + flight
$1,236

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
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$703
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
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$667
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
Phoenix Sky Harbor Intl
Breakfast
3 nights + flight
$949

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 $549; Family holiday $1,647; Romantic holiday $1,647; Budget holiday $2,576.

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)$549
Family holiday (Flight+Hotel)$1,647
Romantic holiday (Flight+Hotel)$1,647
Budget holiday (Flight+Hotel)$2,576