Holidays in Chicago

Holidays in Chicago

2 travellers

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$277 - $628$628 - $977$977 - $1,327$1,327 - $1,677$1,677+ 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
Fort Lauderdale
Meals not included
3 nights + flight
$473
Warwick Allerton Chicago - Chicago - Building
Warwick Allerton Chicago - Chicago - Building
Warwick Allerton Chicago
8.1 Very Good
Near North Side
Free Wi-Fi
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$500
Mccormick Place Guest House - Chicago - Balcony
Mccormick Place Guest House - Chicago - Balcony
Mccormick Place Guest House
5.8 Fair
Douglas
Parking
Free Wi-Fi
Fort Lauderdale
Meals not included
3 nights + flight
$569
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
$466
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$1,189
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Philadelphia
Meals not included
3 nights + flight
$1,050
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
Denver Intl
Breakfast
3 nights + flight
$758
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North - Chicago - Lounge
The Royal Sonesta Chicago River North
8.5 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Denver Intl
Meals not included
3 nights + flight
$625
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile - Chicago
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$606
Aloft Chicago Mag Mile - Chicago - Pool
Aloft Chicago Mag Mile - Chicago - Pool
Aloft Chicago Mag Mile
8.2 Very Good
Near North Side
Free Wi-Fi
Pool
Pet-friendly
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$711
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
Denver Intl
Meals not included
3 nights + flight
$1,237
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
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$1,001
Ivy Boutique Hotel - Chicago - Banquet hall
Ivy Boutique Hotel - Chicago - Banquet hall
Ivy Boutique Hotel
8.4 Very Good
Near North Side
Free Wi-Fi
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$618
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
Philadelphia
Meals not included
3 nights + flight
$1,353
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago
8.6 Very Good
Loop
Free Wi-Fi
Pet-friendly
New Orleans Louis Armstrong
Meals not included
3 nights + flight
$687
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.1 Good
Loop
Free Wi-Fi
Fort Lauderdale
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
New Orleans Louis Armstrong
All-inclusive
3 nights + flight
$984

Last minute holiday packages to Chicago

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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
Philadelphia
Meals not included
3 nights + flight
$795

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 $209; Family holiday $731; Romantic holiday $759; Luxury holiday $731; Budget holiday $759.

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)$209
Family holiday (Flight+Hotel)$731
Romantic holiday (Flight+Hotel)$759
Luxury holiday (Flight+Hotel)$731
Budget holiday (Flight+Hotel)$759