Holidays in Chicago

Holidays in Chicago

2 travellers
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Cheap Chicago package deals

These are the best prices for 26-29 Jun.
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BreakfastHalf boardSelf cateringAll-inclusiveMeals not included

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€200 - €305€305 - €409€409 - €514€514 - €618€618+ 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
Los Angeles
Meals not included
3 nights + flight
€316
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
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€291
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
Los Angeles
Breakfast
3 nights + flight
€380
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
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€256
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
Los Angeles
Meals not included
3 nights + flight
€323
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
Los Angeles
Meals not included
3 nights + flight
€311
The Royal Sonesta Chicago Downtown - Chicago - Building
The Royal Sonesta Chicago Downtown - Chicago - Building
The Royal Sonesta Chicago Downtown
8.8 Very Good
Downtown
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€344
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop - Chicago - Bedroom
Hyatt Place Chicago Downtown/The Loop
8.3 Very Good
Downtown
Free Wi-Fi
Pool
Pet friendly
Air conditioning
Miami
Meals not included
3 nights + flight
€335
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
Downtown
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€309
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bedroom
Hilton Garden Inn Chicago Downtown Riverwalk
8.5 Very Good
Downtown
Free Wi-Fi
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€290
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
Los Angeles
Meals not included
3 nights + flight
€404
The Drake - Chicago - Lobby
The Drake - Chicago - Lobby
The Drake
8.3 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€303
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
Los Angeles
Meals not included
3 nights + flight
€311
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.5 Very Good
Downtown
Free Wi-Fi
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€345
Sofitel Chicago Magnificent Mile - Chicago - Lobby
Sofitel Chicago Magnificent Mile - Chicago - Lobby
Sofitel Chicago Magnificent Mile
8.8 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€374
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection - Chicago - Lounge
The Talbott, Autograph Collection
8.5 Very Good
Near North Side
Free Wi-Fi
Pet friendly
Air conditioning
Los Angeles
Meals not included
3 nights + flight
€325

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
Harrisburg
All-inclusive
3 nights + flight
€553

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
Air conditioning
Boston Logan Intl
Meals not included
3 nights + flight
€787
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
8.2 Very Good
Near North Side
Free Wi-Fi
Pool
Air conditioning
Boston Logan Intl
Meals not included
3 nights + flight
€710
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
Boston Logan Intl
Breakfast
3 nights + flight
€638

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 €130; Family holiday €519; Romantic holiday €519; Budget holiday €519.

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)€130
Family holiday (Flight+Hotel)€519
Romantic holiday (Flight+Hotel)€519
Budget holiday (Flight+Hotel)€519