Holidays in Chicago

Holidays in Chicago

2 travellers

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Cheap Chicago package deals

These are the best prices for 27-30 Apr.
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BreakfastHalf boardSelf cateringAll-inclusiveMeals not included

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$403 - $614$614 - $827$827 - $1,039$1,039 - $1,252$1,252+ 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
Los Angeles
Meals not included
3 nights + flight
$643
The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet-friendly
Los Angeles
Meals not included
3 nights + flight
$645
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lounge
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lounge
Residence Inn by Marriott Chicago Downtown Magnificent Mile
9 Wonderful
Near North Side
Free Wi-Fi
Pet-friendly
Los Angeles
Breakfast
3 nights + flight
$676
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
Sacramento Intl
Meals not included
3 nights + flight
$701
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
Ontario
Meals not included
3 nights + flight
$573
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
Los Angeles
Breakfast
3 nights + flight
$533
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
Meals not included
3 nights + flight
$580
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
Ontario
Meals not included
3 nights + flight
$626
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
New York LaGuardia
Meals not included
3 nights + flight
$592
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
Sacramento Intl
Meals not included
3 nights + flight
$1,149
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
$630
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Ontario
Meals not included
3 nights + flight
$492
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
Meals not included
3 nights + flight
$582
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
Los Angeles
Meals not included
3 nights + flight
$901
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
Ontario
Meals not included
3 nights + flight
$559
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
$1,153

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
Los Angeles
All-inclusive
3 nights + flight
$1,174

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
Toronto Pearson Intl
Meals not included
3 nights + flight
$1,533
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
Toronto Pearson Intl
Meals not included
3 nights + flight
$1,291
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
Toronto Pearson Intl
Breakfast
3 nights + flight
$1,573

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 $570; Family holiday $1,710; Romantic holiday $1,710; Budget holiday $2,673.

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)$570
Family holiday (Flight+Hotel)$1,710
Romantic holiday (Flight+Hotel)$1,710
Budget holiday (Flight+Hotel)$2,673