Holidays in Chicago

Holidays in Chicago

2 travellers

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$208 - $565$565 - $923$923 - $1,280$1,280 - $1,638$1,638+ per night

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Most popular Chicago flight and hotel deals

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Hyatt Regency Mccormick Place - Chicago - Patio
Hyatt Regency Mccormick Place - Chicago - Patio
Hyatt Regency Mccormick Place
8.5 Very Good
Near South Side
Free Wi-Fi
Pool
New York LaGuardia
Meals not included
3 nights + flight
$627
Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom
Admiral Motel By OYO Chicago I-94 - Chicago - Bedroom
Admiral Motel By OYO Chicago I-94
4 Mediocre
South Side
Parking
Pet-friendly
New York LaGuardia
Meals not included
3 nights + flight
$314
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.5 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Atlanta Hartsfield-Jackson
Breakfast
3 nights + flight
$609
21c Museum Hotel Chicago - Chicago - Restaurant
21c Museum Hotel Chicago - Chicago - Restaurant
21c Museum Hotel Chicago
8.4 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$635
Hampton Inn & Suites Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites Chicago Medical District UIC
9.1 Wonderful
Near West Side
Pool
Pet-friendly
Orlando
Breakfast
3 nights + flight
$668
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
New York LaGuardia
Meals not included
3 nights + flight
$612
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop
9 Wonderful
Downtown
Free Wi-Fi
Pet-friendly
Spa
Nashville Intl
Meals not included
3 nights + flight
$679
Eurostars Magnificent Mile - Chicago - Lounge
Eurostars Magnificent Mile - Chicago - Lounge
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
New York LaGuardia
Meals not included
3 nights + flight
$687
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room
The Allegro Royal Sonesta Hotel Chicago Loop - Chicago - Living room
The Allegro Royal Sonesta Hotel Chicago Loop
8.4 Very Good
Downtown
Pet-friendly
Nashville Intl
Meals not included
3 nights + flight
$578
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare - Chicago - Building
Marriott Chicago O'Hare
7.4 Good
O'Hare
Airport shuttle
Free Wi-Fi
Pool
New York LaGuardia
Meals not included
3 nights + flight
$386
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel
8.7 Very Good
Downtown
Pet-friendly
Spa
Nashville Intl
Meals not included
3 nights + flight
$586
The Willows Hotel - Chicago - Lobby
The Willows Hotel - Chicago - Lobby
The Willows Hotel
8 Very Good
Lake View
Free Wi-Fi
Nashville Intl
Meals not included
3 nights + flight
$568
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago - Chicago - Bar
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago - Chicago - Bar
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
8.9 Very Good
Near North Side
Pet-friendly
Nashville Intl
Meals not included
3 nights + flight
$1,064
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago - Chicago - Lobby
Four Seasons Hotel Chicago
8.9 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
New York LaGuardia
Meals not included
3 nights + flight
$1,376
Hyatt Centric The Loop Chicago - Chicago - Pool
Hyatt Centric The Loop Chicago - Chicago - Pool
Hyatt Centric The Loop Chicago
8.6 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$645
Congress Plaza Hotel Chicago - Chicago - Living room
Congress Plaza Hotel Chicago - Chicago - Living room
Congress Plaza Hotel Chicago
7.3 Good
Downtown
Free Wi-Fi
New York LaGuardia
Meals not included
3 nights + flight
$473

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
Pet-friendly
Burbank Bob Hope
All-inclusive
3 nights + flight
$1,341

Last minute holiday packages to Chicago

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Thompson Chicago - Chicago - Living room
Thompson Chicago - Chicago - Living room
Thompson Chicago
8.8 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Dallas/Fort Worth
Meals not included
3 nights + flight
$1,563

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.

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 vacation: Search Chicago holiday packages on KAYAK. KAYAK is a travel tool that searches Chicago trips on hundreds of travel sites to help you find the Chicago package that suits you best. Discover Chicago deals now and book your Chicago flight and hotel today.

Not what you’re looking for? Find thousands of other hotels, flights, car hires and package deals with KAYAK.