Vacation Rentals in Chicago, IL
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Popular vacation rental in Chicago
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All filtersConveniently 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.
$431
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.
$137
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.
$234
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.
$69
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.
$185
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.
$66
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 |
Top-rated Chicago vacation rentals
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.
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.
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.
Other accommodations in Chicago
Find the perfect theme hotel or hostel for your stay in Chicago
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.
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.
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.
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.
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.
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.
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Vacation rentals in popular Illinois cities
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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.