- $ USD
- £ GBP
- ¥ JPY
Chicago Vacation Rentals
- Date Added
- Price (Low » High)
- Price (High » Low)
No Chicago rentals match your criteria.
You can try adjusting the filters or location for more results.
Information about Chicago
Chicago, Illinois – best known as “The Windy City” – is famous as home to the Chicago Bulls, Al Capone, Ferris Beuller’s Day Off and the famous Chicago style deep-dish pizza! One of America’s most prominent financial and economic hubs, this city has a lot to offer even in terms of culture, arts and entertainment - it is considered Paris’ Partner City. Located on the shores of Lake Michigan, the city makes for a popular tourist destination, attracting almost 40 million visitors each year.
Chicago is more or less divided into four areas. The North Side is primarily residential – if you’re lucky you may find a condo for rent along the gorgeous waterfront when visiting. Lincoln Park, which is also located on the waterfront, is famous for the Lincoln Park Zoo and Conservatory. The South Side is where the Museum of Science and Industry are located along with Jackson Park and Washington Park. The West Side is home to University of Illinois at Chicago and more famously Oprah Winfrey’s Harpo Studios. Downtown Chicago is the main commercial and financial district in the city. Grant Park is located in this part of the city. The Chicago Loop, encircled by elevated train tracks, is also part of downtown and holds important buildings like the Chicago Mercantile Exchange.
Chicago Art & Architecture
Chicago’s most prominent features include its dense and unique skyline – in fact the city offers architectural boat tours for tourists to get the best views of the many buildings. Among the city’s skyscrapers, Willis Tower (previously Sears Tower), the Aon Center, the iconic John Hancock Center and Trump International Hotel are most prominent. A trip to the Skydeck awards you with views spanning the four different states of Indiana, Illinois, Michigan & Wisconsin. The Chicago Water Tower located along North Michigan Avenue is an iconic landmark. The city’s outdoors are also sprinkled with works of public art including Cloud Gate and the Crown Fountain in Millenium Park, the Chicago Picasso in Daley Plaza as well as Lorado Taft's Fountain of Time to name a few.
Things to do in Chicago
Have a drink at Signature Room in the John Hancock building to get spectacular views of the city. Walk through Greektown to see the National Hellenic Museum. Spend an evening at Navy Pier, where you will see its iconic Ferris wheel. Catch a show at Steppenwolf Theater in Lincoln Park. Shopping on the Magnificent Mile allows access to an abundance of different boutiques and stores. Chicago also has more than 20 Michelin-starred restaurants, with Alinea boasting three stars –reservations are highly recommended!
For all you art lovers, spend a day at Museum Campus where you will have access to the Adler Planetarium & Astronomy Museum, the Field Museum of Natural History, and the Shedd Aquarium. Other options include the Chicago History Museum, Museum of Contemporary Art and the Art Institute of Chicago. Some of the city’s famous annual events include the Taste of Chicago festival, the Grant Park Music Festival concert series, Lollapalooza and in July you can even see the Chicago Yacht Club's Race to Mackinac. And if you’re looking to get away from urban life, the Cook County Forest Preserves with its forests, streams and lakes is a great option.
Chicago is served by a well connected public transportation consisting of buses and subways. So no matter where you choose your Chicago vacation rental, you will have plenty of options to get to different parts of the city. Rentals are likely to be a better option for accommodation especially if you’re looking for a budget vacation. If you’re looking to stay in a more central location, a lot of people offer apartments for rent along the waterfront – a great way to stay close to all activity. House rentals and Chicago holiday homes are more common in the outskirts.
Vacation Rentals In Chicago
Looking for the perfect vacation rental for your Chicago getaway? Tripping.com’s got your trip covered. Whether you’re seeking a villa, cabin or cottage, Chicago offers 679 affordable homes to choose from, offering far more amenities, space and convenience than the average hotel room. Select from 491 properties with high-speed internet, 130 full with jacuzzi and pool, and 318 homes complete with outdoor patio well-suited for a barbecue with loved ones. Whatever your needs, find the perfect rental that best matches your accommodation style and budget.
Search properties from 10 rental sites in Chicago where the top providers in that area are HomeAway, FlipKey, and Roomorama. There are 286 HomeAway rentals, 120 FlipKey short term rentals and 86 Roomorama vacation rentals.
For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $3,259 a month. Save hundreds with Tripping.com and even book instantly with properties marked “Instabook.” Chicago has hundreds of gorgeous homes with 138 pet-friendly rentals to choose from, perfect for your furry friends. Check out our listings now to get the latest deals, and book the right vacation rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com.
Destinations Close To Chicago
Similar Properties in Chicago, Illinois, United States
Using your search criteria, we found similar rentals for you. Click the button below and we'll send all the inquiries for you:
Thanks for your inquiry!
Head back to our search results to see all of Tripping.com's vacation rentals in Chicago, Illinois, United States. Happy travels!