Holidays in Chicago

Holidays in Chicago

2 travellers

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$435 - $724$724 - $1,014$1,014 - $1,305$1,305 - $1,595$1,595+ 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
Minneapolis St Paul
Meals not included
3 nights + flight
$594
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel - Chicago - Restaurant
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel - Chicago - Restaurant
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
8 Very Good
Loop
Pet-friendly
Boston Logan Intl
Meals not included
3 nights + flight
$568
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites - Chicago - Lounge
Hilton Chicago/Magnificent Mile Suites
8.5 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Fort Lauderdale
Meals not included
3 nights + flight
$737
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.3 Very Good
Loop
Free Wi-Fi
Pet-friendly
Fort Lauderdale
Meals not included
3 nights + flight
$559
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
Fort Lauderdale
Meals not included
3 nights + flight
$687
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
8.9 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Portland
Meals not included
3 nights + flight
$1,045
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection - Chicago - Lounge
The Whitehall Hotel, BW Premier Collection
7.8 Good
Near North Side
Free Wi-Fi
Pet-friendly
Fort Lauderdale
Meals not included
3 nights + flight
$500
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Fort Lauderdale
Meals not included
3 nights + flight
$597
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 Very Good
Loop
Free Wi-Fi
Pet-friendly
Spa
Fort Lauderdale
Breakfast
3 nights + flight
$630
Waldorf Astoria Chicago - Chicago - Bar
Waldorf Astoria Chicago - Chicago - Bar
Waldorf Astoria Chicago
9.2 Wonderful
Near North Side
Pool
Pet-friendly
Spa
Los Angeles Los Angeles
Meals not included
3 nights + flight
$1,147
The Langham Chicago - Chicago - Lounge
The Langham Chicago - Chicago - Lounge
The Langham Chicago
9.4 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Portland
Meals not included
3 nights + flight
$1,380
The Drake - Chicago - Lobby
The Drake - Chicago - Lobby
The Drake
8.3 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Fort Lauderdale
Meals not included
3 nights + flight
$663
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
9 Wonderful
Near North Side
Pet-friendly
Minneapolis St Paul
Meals not included
3 nights + flight
$1,232
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
Pet-friendly
Spa
Newark
Meals not included
3 nights + flight
$1,594
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
Fort Lauderdale
Meals not included
3 nights + flight
$543
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
Fort Lauderdale
Meals not included
3 nights + flight
$715

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
Tampa
All-inclusive
3 nights + flight
$1,097

Last minute holiday packages to Chicago

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The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago - Chicago - Restaurant
The St. Regis Chicago
8.1 Very Good
Loop
Pool
Pet-friendly
Spa
London Heathrow
Meals not included
3 nights + flight
$3,576
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
2.6 Poor
Chatham
Parking
Pet-friendly
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$775
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Pool
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.3 Wonderful
Near West Side
Pool
Pet-friendly
Phoenix Sky Harbor Intl
Breakfast
3 nights + flight
$1,746
Chinatown Hotel - Chicago - Building
Chinatown Hotel - Chicago - Building
Chinatown Hotel
5.6 Fair
Chinatown
Free Wi-Fi
Phoenix Sky Harbor Intl
Meals not included
3 nights + flight
$929

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 $211; Family holiday $737; Romantic holiday $765; Luxury holiday $737; Budget holiday $765.

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)$211
Family holiday (Flight+Hotel)$737
Romantic holiday (Flight+Hotel)$765
Luxury holiday (Flight+Hotel)$737
Budget holiday (Flight+Hotel)$765