Holidays in Chicago

Holidays in Chicago

2 travellers

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Cheap Chicago package deals

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

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$339 - $620$620 - $902$902 - $1,183$1,183 - $1,463$1,463+ per night

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Free breakfastFree internetFree airport shuttleFree parking

Most popular Chicago flight and hotel deals

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Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94 - Chicago - Building
Admiral Motel By OYO Chicago I-94
2.5 Poor
Chatham
Parking
Pet-friendly
Los Angeles
Meals not included
3 nights + flight
$438
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
Minneapolis St Paul
Meals not included
3 nights + flight
$651
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 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Los Angeles
Breakfast
3 nights + flight
$623
Kimpton Gray Hotel - Chicago - Lobby
Kimpton Gray Hotel - Chicago - Lobby
Kimpton Gray Hotel
8.9 Very Good
Loop
Pet-friendly
Los Angeles
Meals not included
3 nights + flight
$760
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
8.2 Very Good
O'Hare
Airport shuttle
Pool
Los Angeles
Meals not included
3 nights + flight
$496
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
$833
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton
8.9 Very Good
Loop
Free Wi-Fi
Spa
Los Angeles
Meals not included
3 nights + flight
$677
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Los Angeles
Meals not included
3 nights + flight
$578
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
8.7 Very Good
Loop
Free Wi-Fi
Pet-friendly
Los Angeles
Breakfast
3 nights + flight
$747
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
Loop
Pet-friendly
Los Angeles
Meals not included
3 nights + flight
$591
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bar
La Quinta Inn & Suites by Wyndham Chicago Downtown - Chicago - Bar
La Quinta Inn & Suites by Wyndham Chicago Downtown
8.1 Very Good
Loop
Free Wi-Fi
Pet-friendly
Spa
Minneapolis St Paul
Breakfast
3 nights + flight
$600
Waldorf Astoria Chicago - Chicago - Bar
Waldorf Astoria Chicago - Chicago - Bar
Waldorf Astoria Chicago
9.2 Wonderful
Near North Side
Pool
Pet-friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$1,334
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare
7.6 Good
O'Hare
Airport shuttle
Free Wi-Fi
Pool
Los Angeles
Meals not included
3 nights + flight
$543
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel
8.5 Very Good
Loop
Pet-friendly
Spa
Los Angeles
Meals not included
3 nights + flight
$846
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.3 Very Good
Loop
Free Wi-Fi
Los Angeles
Meals not included
3 nights + flight
$683
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.8 Very Good
Near North Side
Free Wi-Fi
Pool
Spa
Los Angeles
Meals not included
3 nights + flight
$1,235

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 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
$1,039
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
8.1 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Los Angeles
Meals not included
3 nights + flight
$987
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Meeting room
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.2 Very Good
Near North Side
Free Wi-Fi
Pool
Los Angeles
Meals not included
3 nights + flight
$981

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 $213; Family holiday $745; Romantic holiday $773; Luxury holiday $745; Budget holiday $773.

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)$213
Family holiday (Flight+Hotel)$745
Romantic holiday (Flight+Hotel)$773
Luxury holiday (Flight+Hotel)$745
Budget holiday (Flight+Hotel)$773