1,081 Chicago Holiday Rentals

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Compare Chicago holiday rentals from 12 rental sites including Booking.com, HomeAway, HRS Holidays and more, ranging from $25 to $2113 a night.

Information about Chicago

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 Neighborhoods

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

Start the day off on the right note at one of these eight phenomenal breakfast places in town. Have a drink at Signature Room in the John Hancock building to get spectacular views of the city, or go to one of these five rooftop bars. 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. Nearby Evanston is home to Northwestern University and has beautiful, walkable neighborhoods right near the lake. 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. If you are traveling with kids, follow this guide to exploring Chicago. If you have time, consider heading north to Milwaukee, Wisconsin to experience life in another city.

Chicago Accommodations

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.

Best Chicago neighborhoods to stay in

Chicago is one of the biggest cities in the country, and it’s spread out pretty evenly along Lake Michigan. Here are a our favorite neighborhoods in the Chicago area to stay for vacation: Lincoln Park, Near West Side, Lake View, and Bridgeport.

Things to do in Lincoln Park

This neighborhood speaks true to Chicago’s motto: “City in a Garden”. Businesses and shopping areas are intermixed with residential areas and surrounded by historical buildings and parks. With a variety of different restaurants, bars, and a bustling art scene, Lincoln Park is a must-see neighborhood during your stay in Chicago. During the day, you can head over to Clark Street and catch a bite to eat at one of the cafes or restaurants in the area, or you can walk to Armitage Avenue and get some shopping done. At night, Lincoln Avenue is filled with fun bars and nightlife. For a fun day activity, you can even head over to the Lincoln Park Zoo, check out the Lincoln Park Nature Museum or the spend your day in the Observatory.

Things to do in the Near West Side

If you’re looking for quality dining, the Near West Side is the place to be. With culinary strips like Little Italy and Greektown in the area, your food options are never limited in this neighborhood. For entertainment, the Near West Side is home to the United Center, where you can catch a concert, watch the Chicago Bulls play some basketball, or catch a Blackhawks hockey game. At night, there are a variety of different bars around that cater to new townhome owners. Head over to Jaks Tap after a Bulls game and eat some great BBQ while you enjoy a quick drink before taking the bus home. There are also a few smaller museums in the area, including the National Italian American Sports Hall of Fame, so be sure to check out these places during the day.

Things to do in Lake View

Lakeview is one of the liveliest neighborhoods in Chicago, and is filled with rich culture and entertainment. For shopping, check out store along Southport Avenue for a lot of vintage style clothing. When it’s time to eat, check out Wishbone, a nice BBQ restaurant in the area, or Home Run Inn Pizza, a restaurant new to the Lakeview area. At night, get some ice cream or a milkshake at Bobtail Ice Cream Company, the only Chicago company making homemade ice cream. For drinks, check out Bulerias Tapas Bar, a Mexican-style restaurant, bar and lounge. For a relaxing day, go golfing at the Sydney R. Marovitz Golf Course, one of the best nine-hole golf courses in the Chicago area.

Things to do in Bridgeport

This neighborhood that used to be known to the older, working class is now making its way into national headlines. With cuisines from all over the world, people have been drawn to this Chicago neighborhood. When you’re in town, be sure to check out Maria’s Packaged Goods and Community Bar, a bar known for its craft beer, and featured on Esquire TV as one of the best bars in the U.S. in both 2013 and 2015. If vintage is your thing, check out Monster Island Toys for a throwback to when you were a kid, or Let’s Boogie Records and Tapes, a record store that has all of your favorite vinyl. For some sightseeing, stop in the Zhou B Art Center, a former factory than was transformed into an art gallery.

Vacation Rentals in Chicago

Looking for a vacation rental in Chicago? Tripping.com has 1044 rental homes available in Chicago. Potential renters will find 18 studios, 648 1-bedroom, 205 2-bedroom and 173 rentals with 3 or more bedrooms ranging from $25 a night to $2113 a night. Many of these properties are instantly bookable.

The average price of a nightly rental in Chicago is $326 while the average price of a weekly rental is $788. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Chicago home is $4326.

Wondering if you can bring your favorite dog or cat with you? We have 166 pet friendly vacation rentals available for you. In addition to accommodating pets, Chicago rentals offer a variety of amenities. In particular, 670 rentals have internet and wifi, 457 have TV and/or cable and 213 have a pool or hot tub.

Search properties from 12 rental sites in Chicago where the top providers in that area are Booking.com, HomeAway, and HRS Holidays. There are 377 Booking.com rentals, 346 HomeAway short term rentals and 174 HRS Holidays vacation rentals.