Holidays in Chicago

Holidays in Chicago

2 travellers

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Cheap Chicago package deals

These are the best prices for 1-4 May.
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$298 - $458$458 - $618$618 - $778$778 - $938$938+ per night

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Most popular Chicago flight and hotel deals

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Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lounge
Residence Inn by Marriott Chicago Downtown Magnificent Mile - Chicago - Lounge
Residence Inn by Marriott Chicago Downtown Magnificent Mile
9 Wonderful
Near North Side
Free Wi-Fi
Pet-friendly
Houston George Bush Intcntl
Breakfast
3 nights + flight
$504
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG - Chicago - Lobby
Crowne Plaza Chicago West Loop By IHG
8.2 Very Good
Near West Side
Free Wi-Fi
Pet-friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$418
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel - Chicago - Lounge
Renaissance Chicago O'Hare Suites Hotel
8.1 Very Good
O'Hare
Airport shuttle
Pool
Miami
Meals not included
3 nights + flight
$465
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown - Chicago - Restaurant
Hotel 55 Chicago Downtown
8.3 Very Good
Near North Side
Free Wi-Fi
Pet-friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$422
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago - Chicago - Lounge
Park Hyatt Chicago
9.1 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$654
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC - Chicago - Bedroom
Hampton Inn & Suites by Hilton Chicago Medical District UIC
9.3 Wonderful
Near West Side
Pool
Pet-friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$490
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
Houston George Bush Intcntl
Meals not included
3 nights + flight
$430
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
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$435
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile - Chicago - Bedroom
Eurostars Magnificent Mile
8.7 Very Good
Near North Side
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$396
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop
8.9 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Houston George Bush Intcntl
Breakfast
3 nights + flight
$494
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago - Chicago - Balcony
Waldorf Astoria Chicago
9.2 Wonderful
Near North Side
Pool
Pet-friendly
Spa
Atlanta Hartsfield-Jackson
Meals not included
3 nights + flight
$1,022
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
9.2 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet-friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$593
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bar
Hilton Garden Inn Chicago Downtown Riverwalk - Chicago - Bar
Hilton Garden Inn Chicago Downtown Riverwalk
8.4 Very Good
Downtown
Free Wi-Fi
Pet-friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$423
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago - Chicago - Bedroom
Sports Illustrated Resorts Chicago
8.6 Very Good
Downtown
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$478
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
Houston George Bush Intcntl
Meals not included
3 nights + flight
$478
Freehand Chicago - Chicago - Lounge
Freehand Chicago - Chicago - Lounge
Freehand Chicago
7.2 Good
Near North Side
Free Wi-Fi
Pet-friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$372

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
Atlanta Hartsfield-Jackson
All-inclusive
3 nights + flight
$1,456

Last minute holiday packages to Chicago

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The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy - Chicago - Living room
The Neighborhood Hotel Little Italy
Near West Side
Houston George Bush Intcntl
Meals not included
3 nights + flight
$829
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
Houston George Bush Intcntl
Meals not included
3 nights + flight
$393
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
Houston George Bush Intcntl
Breakfast
3 nights + flight
$473

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 $557; Family holiday $1,672; Romantic holiday $1,672; Budget holiday $2,615.

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)$557
Family holiday (Flight+Hotel)$1,672
Romantic holiday (Flight+Hotel)$1,672
Budget holiday (Flight+Hotel)$2,615