Vacation Rentals in Chicago, IL

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Chicago, IL, United States
sep. 21 — sep. 222
Chicago, IL, United States
jue. 9/21
vie. 9/22
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Popular vacation rental in Chicago

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The Penthouse at Grand Plaza
The Penthouse at Grand Plaza
9.1 Excellent
540 North State Street, Chicago, IL, United States
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1.1 mi from city center, Chicago, IL, United States 
ExcellentBased on 70 reviews
9.1

Conveniently located in the middle of the city, this 4-star property makes for an excellent base in Chicago. It also offers a sauna, an outdoor pool and free Wi-Fi.

Stay Alfred at Park Michigan
Stay Alfred at Park Michigan
Chicago, IL, United States
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0.6 mi from city center, Chicago, IL, United States 

Stay Alfred at Park Michigan provides comfortable accommodation in the heart of Chicago. Those staying at the property can also take advantage of complimentary wireless internet throughout their stay.

Apartment in River North Downtown Chicago
Apartment in River North Downtown Chicago
Chicago, IL, United States
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1.6 mi from city center, Chicago, IL, United States 

This comfortable property in Chicago offers complimentary wireless internet, as well as an outdoor pool and a swimming pool. It is conveniently located in the city centre.

Stay Alfred at The Seneca
200 East Chestnut Street, Chicago, IL, United States
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1.6 mi from city center, Chicago, IL, United States 

Centrally situated, Stay Alfred at The Seneca allows for easy access to Chicago's best tourist attractions. It also offers laundry facilities, a lift and free Wi-Fi.

Furnished Suites in South Loop Chicago
Furnished Suites in South Loop Chicago
Chicago, IL, United States
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0.8 mi from city center, Chicago, IL, United States 

Strategically located in the heart of the city, this 4.5-star property makes for an ideal base in Chicago. It also offers laundry facilities, a concierge and free Wi-Fi.

Celeste Celebrity Suites
Celeste Celebrity Suites
Chicago, IL, United States
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1.8 mi from city center, Chicago, IL, United States 

Centrally located, Celeste Celebrity Suites offers easy access to Chicago's best hot spots. It provides free Wi-Fi and room service, and is a brief stroll from John Hancock Center, Michigan Avenue and John Hancock Center Observatory.

Tips for booking vacation rentals in Chicago

Cheapest month:April
Most expensive month:August
Average price in Chicago:$277/night
Cheapest price found:$78/night
Cheapest day:Saturday
Most expensive day:Thursday
$107 - $600
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
$196 - $870
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

Top-rated Chicago vacation rentals

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1
The Chicago Hotel Collection - Millennium Park
3.8 Mediocre
55 East Washington Street, Chicago, IL, United States
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0.5 mi from city center, Chicago, IL, United States 

Centrally situated, Pittsfield Apartments + Suites allows for easy access to Chicago's best hot spots. It offers complimentary Wi-Fi, an express check-in and check-out feature and a swimming pool.

$397
Avg. per night

Cheapest vacation rentals in Chicago, Illinois

These are the lowest prices we've found on vacation rentals in Chicago at the moment. If you have the flexibility, change the dates selected to compare prices.
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Corporate Suites in the Heart of Magnificent Mile
Corporate Suites in the Heart of Magnificent Mile
Chicago, IL, United States
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1.1 mi from city center, Chicago, IL, United States 

Strategically located in the centre of the city, this 4-star property makes for an excellent base in Chicago. It offers an indoor pool and free Wi-Fi, and is a brief stroll from Michigan Avenue and Magnificent Mile.

$94
Avg. per night

Other accommodations in Chicago

Find the perfect theme hotel or hostel for your stay in Chicago
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Warwick Allerton Chicago
7.2 Good
701 North Michigan Avenue, Chicago, IL, United States
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1.3 mi from city center, Chicago, IL, United States 

Strategically located in the heart of the city, this 4-star hotel makes for an excellent base in Chicago. It is close to Magnificent Mile, dining options and shops.

$127
Avg. per night
Chicago Lake Shore Hotel
6.5 Good
4900 South Lake Shore Drive, Chicago, IL, United States
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5.3 mi from city center, Chicago, IL, United States 

Situated in Chicago, the hotel is within a 20-minute drive of Chicago Midway International Airport and provides free wireless internet access in all areas. It also offers a free shuttle service, a seasonal outdoor swimming pool and a lake.

$128
Avg. per night
HI Chicago Hostel
8.1 Excellent
24 E Ida B Wells Drive, Chicago, IL, United States
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0.0 mi from city center, Chicago, IL, United States 

Centrally situated, HI Chicago Hostel allows for easy access to Chicago's main sightseeing areas. It is located a brief stroll from Chicago Board of Trade Building and Grant Park.

$35
Avg. per night
Wrigley Hostel
8.1 Excellent
3514 North Sheffield Avenue, Chicago, IL, United States
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5.0 mi from city center, Chicago, IL, United States 

This Chicago hostel is located within a 10-minute walk of Belmont CTA North Side Main Line Railway Station. It is situated in the area's vibrant nightlife district, which is only a few minutes walk from Wrigley Field.

$40
Avg. per night
Chicago Getaway Hostel
8.3 Excellent
616 West Arlington Place, Chicago, IL, United States
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3.6 mi from city center, Chicago, IL, United States 

Located in Chicago, the hostel is a short drive from Michigan Avenue and the Art Institute of Chicago. It is situated in close proximity to plenty of popular bars, clubs and restaurants.

$47
Avg. per night

Where to stay in Chicago

Use the map to find vacation rentals in Chicago that are close to the points of interest you'll be frequenting. Clicking on a vacation rental name will take you to a page with pricing, reviews, and more useful information.

Facts about staying in Chicago

  • How much does a vacation rental in Chicago cost?

    $277 per night is how much a vacation rental in Chicago costs, on average. $79 per night was the cheapest price recently found by our users, though anything for $254 per night or less is a good deal. Keep in mind that Chicago vacation rental prices fluctuate throughout the year: the most expensive month to book is August, and the cheapest time to book is April.

  • What is the best Chicago vacation rental?

    The Chicago Hotel Collection - Millennium Park has a 3.8 rating from 9 users, making it the best Chicago vacation rental based on our data.

  • What’s the closest vacation rental to Chicago O'Hare Intl Airport?

    It’s only 15.2 mi from Chicago O'Hare Intl Airport to River North Waterside Condos (the nearest Chicago vacation rental to the airport).

  • What part of Chicago is best to stay in?

    The best neighborhood to stay in Chicago is Downtown, according to our user data. 0% of our users who looked for vacation rentals in Chicago searched for properties in the Downtown area. If you’re also interested in booking a vacation rental in Downtown, consider the 4 #1S - 4 Bedroom / 1.5 Bath Condo near McCormick Place, Wintrust Arena - the neighborhood’s most popular rental property.

  • What’s the most popular vacation rental in Chicago near Navy Pier?

    If you’re looking for a vacation rental close to Navy Pier while in Chicago, then the most popular is The Chicago Hotel Collection - Millennium Park with a 3.8/10 review score from 9 users. The distance from Navy Pier to The Chicago Hotel Collection - Millennium Park is 1.3 mi.

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