Holidays in Chicago

Holidays in Chicago

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Cheap Chicago package deals

These are the best prices for 31 May - 3 Jun.
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€193 - €309€309 - €424€424 - €540€540 - €655€655+ 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
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€373
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Hotels Chicago Magnificent Mile By IHG - Chicago - Lobby
Intercontinental Hotels Chicago Magnificent Mile By IHG
8.1 Very Good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Little Rock
Meals not included
3 nights + flight
€437
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel - Chicago - Building
Omni Chicago Hotel
8.9 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€401
Chicago Marriott Downtown Magnificent Mile - Chicago - Building
Chicago Marriott Downtown Magnificent Mile - Chicago - Building
Chicago Marriott Downtown Magnificent Mile
8.5 Very Good
Near North Side
Air conditioning
Las Vegas Harry Reid Intl
Breakfast
3 nights + flight
€403
Hilton Chicago - Chicago - Living room
Hilton Chicago - Chicago - Living room
Hilton Chicago
7.8 Good
Downtown
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€381
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile - Chicago - Building
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
7.9 Good
Near North Side
Pool
Pet friendly
Air conditioning
Las Vegas Harry Reid Intl
Breakfast
3 nights + flight
€420
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton
8.9 Very Good
Downtown
Free Wi-Fi
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€461
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
Air conditioning
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
€411
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop - Chicago - Bedroom
Staypineapple, An Iconic Hotel, The Loop
8.9 Very Good
Downtown
Free Wi-Fi
Pet friendly
Air conditioning
Little Rock
Meals not included
3 nights + flight
€410
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€362
Hampton Inn Chicago Downtown/N Loop/Michigan Ave - Chicago - Lobby
Hampton Inn Chicago Downtown/N Loop/Michigan Ave - Chicago - Lobby
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
7.9 Good
Downtown
Free Wi-Fi
Pet friendly
Air conditioning
Little Rock
Breakfast
3 nights + flight
€386
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
Air conditioning
Austin Bergstrom
Meals not included
3 nights + flight
€510
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel
8.6 Very Good
Downtown
Pet friendly
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€475
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago
8.2 Very Good
Near North Side
Pet friendly
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€387
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago - Chicago - Balcony
Hyatt Centric The Loop Chicago
8.6 Very Good
Downtown
Free Wi-Fi
Pet friendly
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€483
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel - Chicago - Lobby
Congress Plaza Hotel
7.2 Good
Downtown
Free Wi-Fi
Air conditioning
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
€319

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
Air conditioning
Austin Bergstrom
All-inclusive
3 nights + flight
€513

Last minute holiday packages to Chicago

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Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical - Chicago - Lounge
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical - Chicago - Lounge
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
8.2 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
New York LaGuardia
Breakfast
3 nights + flight
€691
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile - Chicago - Lobby
Courtyard by Marriott Chicago Downtown/Magnificent Mile
8.3 Very Good
Near North Side
Free Wi-Fi
Pool
Air conditioning
San Jose
Meals not included
3 nights + flight
€884
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.7 Very Good
Near West Side
Free Wi-Fi
Pet friendly
Air conditioning
New York LaGuardia
Breakfast
3 nights + flight
€842

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 €129; Family holiday €515; Romantic holiday €515; Budget holiday €515.

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)€129
Family holiday (Flight+Hotel)€515
Romantic holiday (Flight+Hotel)€515
Budget holiday (Flight+Hotel)€515