Vacations in Chicago

Vacations in Chicago

2 travelers

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$167 - $343$343 - $520$520 - $696$696 - $872$872+ per night

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Most popular Chicago flight and hotel deals

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Residence Inn by Marriott Chicago Downtown/River North - Chicago - Lounge
Residence Inn by Marriott Chicago Downtown/River North - Chicago - Lounge
Residence Inn by Marriott Chicago Downtown/River North
8.4 Very good
Near North Side
Free Wi-Fi
Pet friendly
Orlando
Meals not included
3 nights + flight
$276
L7 Chicago by LOTTE - Chicago - Lounge
L7 Chicago by LOTTE - Chicago - Lounge
L7 Chicago by LOTTE
9.1 Wonderful
Downtown
Free Wi-Fi
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
$398
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
9 Wonderful
Near North Side
Free Wi-Fi
Pool
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$352
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
Houston George Bush Intcntl
Meals not included
3 nights + flight
$248
Hampton Inn & Suites Chicago-Downtown - Chicago - Lobby
Hampton Inn & Suites Chicago-Downtown - Chicago - Lobby
Hampton Inn & Suites Chicago-Downtown
8.5 Very good
Near North Side
Free Wi-Fi
Pool
Pet friendly
Houston George Bush Intcntl
Breakfast
3 nights + flight
$200
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop
8.9 Very good
Downtown
Free Wi-Fi
Pet friendly
Spa
Boston Logan Intl
Meals not included
3 nights + flight
$362
Eurostars Magnificent Mile - Chicago - Lounge
Eurostars Magnificent Mile - Chicago - Lounge
Eurostars Magnificent Mile
8.6 Very good
Near North Side
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$253
JW Marriott Chicago - Chicago - Lounge
JW Marriott Chicago - Chicago - Lounge
JW Marriott Chicago
8.6 Very good
Downtown
Pool
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$459
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy - Chicago - Living room
The Neighborhood Hotel-Little Italy
Near West Side
Orlando
Meals not included
3 nights + flight
$467
Travelodge by Wyndham Downtown Chicago - Chicago - Lounge
Travelodge by Wyndham Downtown Chicago - Chicago - Lounge
Travelodge by Wyndham Downtown Chicago
7.1 Good
Downtown
Free Wi-Fi
Houston George Bush Intcntl
Meals not included
3 nights + flight
$192
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
7.8 Good
Downtown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Breakfast
3 nights + flight
$212
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
Orlando
Meals not included
3 nights + flight
$266
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago - Chicago - Front desk
The Westin Michigan Avenue Chicago
8.3 Very good
Near North Side
Pet friendly
Spa
Houston George Bush Intcntl
Meals not included
3 nights + flight
$307
Virgin Hotels Chicago - Chicago - Building
Virgin Hotels Chicago - Chicago - Building
Virgin Hotels Chicago
8.6 Very good
Downtown
Free Wi-Fi
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
$382
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
8.2 Very good
Downtown
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$184
Sofitel Chicago Magnificent Mile - Chicago - Patio
Sofitel Chicago Magnificent Mile - Chicago - Patio
Sofitel Chicago Magnificent Mile
8.9 Very good
Near North Side
Free Wi-Fi
Pet friendly
Houston George Bush Intcntl
Meals not included
3 nights + flight
$299

All inclusive vacation 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
Orlando
All inclusive
3 nights + flight
$984

Last minute vacation packages to Chicago

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Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District - Chicago - Building
Hyatt House Chicago Medical/University District
8.5 Very good
Near West Side
Free Wi-Fi
Pet friendly
Boston Logan Intl
Breakfast
3 nights + flight
$462

When to book a vacation in Chicago

Price includes flights and 3 nights accommodation for 2 travelers. Prices are not fixed and may vary with time.

Tips for finding Chicago package deals

  • There are loads of types of vacations 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 travelers: Top vacation $312; Family vacation $302; Romantic vacation $332; Luxury vacation $320; Budget vacation $237.

Where to stay in Chicago

Our map will help you find the perfect place to stay for your vacation in Chicago by showing you the exact location of each hotel.

Everything you need to know for your vacation in Chicago

Chicago vacation information

Top vacation (Flight+Hotel)$312
Family vacation (Flight+Hotel)$302
Romantic vacation (Flight+Hotel)$332
Luxury vacation (Flight+Hotel)$320
Budget vacation (Flight+Hotel)$237

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