Holidays in Chicago

Holidays in Chicago

2 travellers

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Cheap Chicago package deals

These are the best prices for 16-19 Aug.
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BreakfastHalf boardSelf cateringAll-inclusiveMeals not included

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$308 - $658$658 - $1,009$1,009 - $1,361$1,361 - $1,712$1,712+ per night

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Free breakfastFree internetFree airport shuttleFree parking

Most popular Chicago flight and hotel deals

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The Wade - Chicago - Lobby
The Wade - Chicago - Lobby
The Wade
7.9 Good
Near North Side
Pool
Pet-friendly
Baltimore/Washington
Meals not included
3 nights + flight
$752
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Building
Intercontinental Hotels Chicago Magnificent Mile By IHG
8.1 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Toronto Island
Meals not included
3 nights + flight
$826
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
2.7 Poor
Chatham
Parking
Pet-friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$384
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
Baltimore/Washington
Meals not included
3 nights + flight
$749
City Suites Hotel - Chicago - Bedroom
City Suites Hotel - Chicago - Bedroom
City Suites Hotel
8.3 Very Good
Lake View
Free Wi-Fi
Baltimore/Washington
Meals not included
3 nights + flight
$588
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.4 Very Good
Loop
Free Wi-Fi
Pet-friendly
Baltimore/Washington
Meals not included
3 nights + flight
$705
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
Minneapolis St Paul
Meals not included
3 nights + flight
$725
Motel Edgebrook Chicago North Shore By OYO - Chicago - Bedroom
Motel Edgebrook Chicago North Shore By OYO - Chicago - Bedroom
Motel Edgebrook Chicago North Shore By OYO
6 Okay
Forest Glen
Parking
Free Wi-Fi
Minneapolis St Paul
Meals not included
3 nights + flight
$307
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Baltimore/Washington
Meals not included
3 nights + flight
$610
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
Minneapolis St Paul
Meals not included
3 nights + flight
$645
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.3 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
San Diego
Meals not included
3 nights + flight
$1,198
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
Minneapolis St Paul
Meals not included
3 nights + flight
$830
ACME Hotel Chicago, Outset Collection by Hilton - Chicago - Bar
ACME Hotel Chicago, Outset Collection by Hilton - Chicago - Bar
ACME Hotel Chicago, Outset Collection by Hilton
8.3 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Spa
Baltimore/Washington
Meals not included
3 nights + flight
$593
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
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$1,342
Club Quarters Hotel Wacker at Michigan, Chicago - Chicago - Building
Club Quarters Hotel Wacker at Michigan, Chicago - Chicago - Building
Club Quarters Hotel Wacker at Michigan, Chicago
8.3 Very Good
Loop
Free Wi-Fi
Pet-friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$599
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection
8.3 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Baltimore/Washington
Meals not included
3 nights + flight
$809

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
$1,257

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
$1,468
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.8 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Los Angeles
Breakfast
3 nights + flight
$1,255
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Meeting room
SpringHill Suites by Marriott Chicago Chinatown - Chicago - Meeting room
SpringHill Suites by Marriott Chicago Chinatown
9 Wonderful
Chinatown
Free Wi-Fi
Los Angeles
Breakfast
3 nights + flight
$1,687

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 $260; Family holiday $1,689; Romantic holiday $781; Luxury holiday $752; Budget holiday $781.

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)$260
Family holiday (Flight+Hotel)$1,689
Romantic holiday (Flight+Hotel)$781
Luxury holiday (Flight+Hotel)$752
Budget holiday (Flight+Hotel)$781