Find Vacation Rentals in Chicago

Highlights Chicago

  • World class galleries and museums
  • Sporting spectacles
  • Beautiful skyline
  • Lakefront setting
  • Good public transportation
  • Shopping

Best Vacation Rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation Rental for 8 Guests in Chicago, Cook County
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Chicago, Cook County
Vacation Rental • 8 Guests • 4 Bedrooms
(108 reviews)
"Best in the City" - Chicago Magazine. Ruby Room Inn & Spa is one of Chicago's most unique overnight destinations. Just 8 minutes from downtown, in the heart of historic Wicker Park's restaurant, shopping and nightlife scene. Modeled in the European tradition, Ruby Room is neither a hotel nor a traditional B&B. Our concept is an urban inn. By design, we do not offer telephones or televisions. We do not offer 24 hour reception or bellman services. Ruby Room is a historic property and does not offer an elevator. Please keep this in mind, if you or any of your guests have a challenge w...
from $101 / night
Vacation Rental for 2 Guests in Chicago, Cook County
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Chicago, Cook County
Vacation Rental • 549 ft² • 2 Bedrooms
(10 reviews)
Just a long line drive and outfielder’s throw away from fabled Wrigley Field (home of the Chicago Cubs, doncha know?) this home away from home (plate) has all the amenities you crave, tastefully poured into a surprisingly spacious studio unit. Bright, cozy, and full of goodies, this compact apartment comes replete with a full kitchen and laundry facilities, as well as a balcony from which to catch any stray grand slams. The handy-dandy nature of this studio space extends beyond the front door; with a coffee shop in the building and a grocery store on the corner, you’ll feel right at home wh...
from $193 / night
Vacation Rental for 3 Guests in Chicago, Cook County
Vacation Rental for 3 Guests in Chicago, Cook County, Picture 1
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Chicago, Cook County
Vacation Rental • 592 ft² • 1 Bedroom
(7 reviews)
Unique neighborhood, unique building, unique suite. This 1-bedroom, 1-bath apartment in the beautiful Del Prado building lends your travels a hint of luxury. Enjoy a fully stocked kitchen, art deco-inspired furnishings, and fresh linens, all to make your travels seamless and comfortable. Hyde Park, home to the prestigious University of Chicago and the Museum of Science and Industry, is a culturally rich neighborhood full of eclectic shops, restaurants, and small businesses. Enjoy a stroll in one of the area’s many parks—or explore Chicago by bike when you hop on the Lakefront Trail and crui...
from $146 / night

Popular Destinations in Chicago

Prices and availability

Current Vacation rental prices in Chicago

$524for 3 Jun - 10 Jun
$521 annual average
Average price per week

Current vacation rental availability in Chicago

1%for 3 Jun - 10 Jun
28% annual average
Percentage of available rentals

Chicago Vacation Rentals

Elegant City Center Vacation Homes

America’s third largest city, Chicago is full of wonderful vacation rental options. For example, if you look inside the Loop, you’ll find plenty of upscale apartment properties, with multiple bathrooms, bedrooms and huge living areas – all within walking distance of the subway and major attractions.

Choose a Lakefront Vacation Home or a Suburban Villa

You don’t need to stay in the center of Chicago. One of the great things about the city is the beautiful shorefront of Lake Michigan. Check out lakefront neighborhoods like Lincoln Park, the Near North Side or Gold Coast. Or look inland to roomy vacation rental options in affluent suburbs like Wheaton or Itasca. There’s no shortage of fantastic accommodation possibilities in the Windy City.

Vacationing in Chicago

A Lakefront Metropolis with Incredible Energy

Chicago is clustered around the southern curve of Lake Michigan in the state of Illinois, roughly a quarter of the distance from New York to California. The gateway to the Midwest, Chicago is easy to reach thanks to O’Hare International Airport, which connects the city to every state in the US, and international destinations as well.

Find the Loop, and You’ve Found Chicago’s Downtown Center

In the city itself, the lake is an easy reference point. Chicago’s city center is nestled up against the lake, inside what locals call “the Loop” – which referred to the route of the elevated railway. Nowadays, the L Train network runs into the Loop from north, south, and the west, and it’s the focal point for most tourist visits.

Hundreds of Neighborhoods to Explore

However, Chicago is a massive city, with over 10 million people in the metro area. Within that area, there are plenty of sights and areas to explore, from Frank Lloyd Wright houses in Hyde Park to BrookfieldZoo. It’s all fairly spread out, so renting a car and choosing a rental home with parking space makes perfect sense.

Downtown Chicago
Downtown Chicago


A World Class Cultural Destination

Chicago has an endless array of cultural attractions. There’s a huge Blues Festival in June, the delights of the Art Institute of Chicago, the huge Field Museum and the Museum of Science. If you love art, science or music, you can’t go wrong in Chicago.

Sporting Attractions All Year-Round

Chicago is also a major sporting destination. From the NFL’s Bears to the Bulls of the NBA and Major League Baseball’s Cubs, sports fans will have an excuse to visit the city at almost any time of year.

A Superb Place if You Love to Shop

The home of Sears is a major shopping hub for the Midwest. For those who need some retail therapy, the Magnificent Mile on Michigan Avenue hosts one of the highest concentrations of boutiques in the USA, while State Street is home to huge department stores like Marshall Field's.

The famous Route 66 highway begins right outside the doors of the Art Institute of Chicago

Top 5 things to do in Chicago

1. Visit the city’s huge number of museums

Chicago’s museum collection is incredible. The Field Museum is a massive natural history center, the Art Institute hosts a huge collection of modern art, the Chicago History Museum teaches visitors about the city’s fascinating past, while the Science Museum immerses guests in the world of technology.

2. Ascend to the panoramic deck of the John Hancock Center

There’s no better place to witness the breathtaking skyline of Chicago than the observation deck of the soaring John Hancock Tower, which is accessible by a high-speed elevator (which is an attraction in itself). Be sure to take your camera.

3. Explore the Chicago Riverwalk

The south bank of the Chicago River has been turned into one of America’s finest urban walkways, with attractions like tiki bars, birdwatching tours, water taxis, wine bars and brewery pubs dotted along its route.

4. Try a Chicago deep dish pizza

Deep dish pizza is one of Chicago’s culinary specialties. If you want to try a slice, head to local institutions like Pequod’s, the Art of Pizza or Giordano’s for a pizza pie that you will never forget.

5. Head to Soldier Field, Wrigley Field or the United Center for sporting action

Chicago’s teams are all in the top bracket of their sports, so whether you love NFL, NBA, Major League Baseball or even soccer or hockey, be sure to catch a contest during your stay.

The Chicago Loop
The Chicago Loop

Useful Information


Chicago’s climate is something to think about if you are planning a visit. Because of its location at the center of the continent, Chicago experiences extremely cold winters (and the legendary wind), and hot summers. Visit in fall or late spring for the best sightseeing conditions. However, summer is festival season in Chicago, so if you are keen to attend open air music concerts, you’ll want to visit between June and September.

Getting Around

Getting around the city is fairly easy. You can travel from most suburban vacation rental home options via CTA buses or trains. If you do rely on public transportation, be sure to investigate day and week passes, as they are a great way to save money. You can also purchase City Passes to reduce the cost of visiting the major attractions.

FAQs: Vacation Rentals in Chicago

On average, what was the cost for vacation rentals in Chicago last year?

Last year, rentals in this destination had an annual average price of around $369 per night.

During which months can you find the best price for vacation rentals in Chicago?

If you would like to save as much as possible during your visit to Chicago, pack your bags and travel there in February ($307 per night on average), April ($312), or March ($313), to find the lowest prices for the whole year.

When does the price of vacation rentals in Chicago go up the most?

When it comes to looking for a vacation rental in Chicago, the most expensive months are, in order of highest to lowest, September, August and October, with average prices per night of $432, $413, and $409, respectively.

Should I plan a trip to Chicago well in advance?

If you decide to put Chicago on your bucket list, we suggest planning your visit long before you go because it is usually very high in demand, with an annual average of 82% of rentals booked the previous year.

Which months offer the highest availability?

February, May and January are, in order of highest to lowest, the months offering the largest number of accommodations available, with an average availability of 27%, 26%, and 24%. However, even during these months, when the availability is the highest, the average is just 25%. So we highly recommend you always book your vacation early in Chicago.

When are fewer rentals available in Chicago?

During this period, the availability is only 9%. It is therefore preferable to book early.

Are there many rentals in Chicago?

In Chicago we offer you an extensive catalog of around 720 properties, with options to suit everyone, thanks to our 6 local and international providers.

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