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- World class galleries and museums
- Sporting spectacles
- Beautiful skyline
- Lakefront setting
- Good public transportation
Most popular in Chicago
Prices and availability
Chicago Vacation Rentals
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
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.
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
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.
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
The COVID-19 pandemic strongly impacted travel in 2020. Last year, rentals in Chicago had an annual average price of around $336.90 per night.
If it is your aim to save the maximum during your vacation to Chicago, travel in January ($270.91 per night on average), December ($285.31), or February ($297.14), to find the lowest prices for the whole year.
At the time of booking a vacation rental in Chicago, the highest prices are usually seen in the month of August (with an average of $386.83 per night), followed by July ($383.64), and September ($368.12).
We recommend you to book in advance in Chicago as only 31% of the accommodations are free throughout the year, following the data observed in 2020.
The most available months are, on average, January (with an availability of 43%), April (42%), and June (34.75%), according to the trends observed in 2020.
According to data from 2020, the months with the fewest housing options available in Chicago are, in order, October (with 22.4% of available rentals), August (26.8%), and July (27.25%).
We have grouped together the offers from 8 different partners in Chicago, so we can offer you around 1200 properties. You're going to have a hard time choosing your favorite!