Holidays in Chicago

Holidays in Chicago

2 travellers

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$275 - $638$638 - $1,002$1,002 - $1,364$1,364 - $1,727$1,727+ per night

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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
Charlotte Douglas
Meals not included
3 nights + flight
$599
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
Charlotte Douglas
Meals not included
3 nights + flight
$616
River Hotel - Chicago - Property amenity
River Hotel - Chicago - Property amenity
River Hotel
8.3 Very Good
Loop
Free Wi-Fi
Pet-friendly
Charlotte Douglas
Meals not included
3 nights + flight
$554
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
$512
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
8.9 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Charlotte Douglas
Meals not included
3 nights + flight
$966
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
Charlotte Douglas
Meals not included
3 nights + flight
$491
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Charlotte Douglas
Meals not included
3 nights + flight
$624
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
$595
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
$1,204
The Drake - Chicago - Lobby
The Drake - Chicago - Lobby
The Drake
8.3 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Newark
Meals not included
3 nights + flight
$676
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
Newark
Meals not included
3 nights + flight
$1,233
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
Charlotte Douglas
Meals not included
3 nights + flight
$1,580
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel - Chicago - Lobby
Central Loop Hotel
8.1 Very Good
Loop
Free Wi-Fi
Pet-friendly
Fort Lauderdale
Meals not included
3 nights + flight
$536
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
Charlotte Douglas
Meals not included
3 nights + flight
$578
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
$752
Club Quarters Hotel Central Loop, Chicago - Chicago - Lobby
Club Quarters Hotel Central Loop, Chicago - Chicago - Lobby
Club Quarters Hotel Central Loop, Chicago
8.2 Very Good
Loop
Free Wi-Fi
Pet-friendly
Fort Lauderdale
Meals not included
3 nights + flight
$529

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
Fort Lauderdale
All-inclusive
3 nights + flight
$1,071

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