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Chicago Vacation Rentals

Chicago Travel Guide

Chicago is one of the largest metropolitan areas in the United States. Sitting by lake Michigan, the city's characteristic architecture, culture, and overall cosmopolitan scene make it a top destination for travelers from all around the world.

Things to Do in Chicago

Known as The Windy City, Chicago has a wide array of cultural sites and attractions for people visiting. Some of the more popular ones are Millennium Park, where the iconic Cloud Gate sculpture stands, the Art Institute of Chicago, and the downtown area with skyscrapers like Willis Tower and John Hancock Center. It is literally impossible to get bored in Chicago. The city offers an almost infinite amount of restaurants, bars, and clubs offering a lively nightlife and staple dishes like deep-dish pizza and delicious hot dogs.

Best Time to Visit Chicago

The weather in Chicago enjoys well-marked seasons, with summer (June to August) being the most popular time to visit. There are literally millions of things to do and places to see in Chicago, so plan ahead and maybe make your trip coincide with fun events such as St. Patrick's Day, Taste of Chicago culinary festival in July, or the Jazz Festival in September. The holiday season, November to January, is also a good time to visit Chicago and experience celebrations like the Magnificent Mile Lights Festival and the German Christmas market.

A Local's Guide to Chicago

Vactioners should check out one of the largest cities in the USA -- Chicago. Known as the Windy City, Chicago certainly has lots to fill a vacation, including bold architecture and a city skyline full of iconic buildings like the John Hancock Center, 1,451-ft. Willis Tower (formerly the Sears Tower) and the neo-Gothic Tribune Tower.

Other great activities range from art galleries, restaurants, and a vibrant music scene that establishes Chicago as a popular vacation destination.

There is so much to do in Chicago for friend, family and group vacations. Sports fans can watch a Bears, Bulls, White Sox, Blackhawks, Sky or Fire home game. Basketball fans can also grab a picture with the Michael Jordon statue in the city. Baseball fans should take a trip to the north side of Chicago to watch a Chicago Cubs game. The club has been playing at this field for more than 100 years and is the perfect place to soak up some history while watching a game.

For active travelers, Grant Skate Park offers multi-skilled areas for skateboarders and BMX bikers. There are ramps, rails and landscaping to challenge novices and pros. This stunning park also has views of the city and lake.

Art lovers will also have plenty to see as the city is also renowned for its museums, including the Art Institute of Chicago with its Impressionist and Post-Impressionist works.

Elsewhere, thrill-seekers should take a trip to The Ledge at Skydeck in Willis Tower. This observation point has a glass floor which allows brave visitors to stand more than 1,300ft above the city. Or the John Hancock Center, now called the 360 CHICAGO observation deck stands 1,000ft above the busy Chicago streets. Elsewhere, TILT is the highest ride in Chicago and puts daredevils out onto a moving platform that tilts over Michigan Avenue.

All year round there are fireworks and a 196-ft Ferris Wheel at Navy Pier, as well as top attractions like the Field Museum, Adler Planetarium, and the Shedd Aquarium which are open all seasons.

Lake Michigan has some great places to walk including the Lakefront Trails, which are perfect for a day in the great oudoors with the family. The Lurie Gardens, Lincoln Park Zoo and one of Chicago’s lakefront beaches are also picturesque places to spend the afternoon.

Visitors with a head for heights can scale a 40ft climbing wall with views of the city skyline at Maggie Daley Park and the award-winning Chicago Riverwalk is open to river kayakers who can paddle through the architectural canyon.

Millennium Park is a great place to spend an evening as the vibrant area has lots to offer visitors. There’s a state-of-the-art collection of architecture, landscape design and art within the park and throughout the year there are hundreds of free concerts, exhibitions, tours and activities.

Vacation rentals are available across the city from downtown Chicago to the magnificent mile and Wicker Park. There is a vacation home that suits every party size, budget and vacation must-do list. Choosing a vacation home within 1.2 miles of the main attractions is easy but as Chicago has great public transport systems, it is simple for travelers to get around.

Price and Availability in Chicago

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The most expensive month to stay in a vacation rental in Chicago is in June, while the cheapest month is in February. The most popular time to book a vacation rental in Chicago is in the high season in June. Chicago has its low season in January, when less people are visiting and the vacation home occupancy rate drops.
The cheapest day to stay at a vacation rental in Chicago tends to be Wednesday, while the most expensive day tends to be Saturday. Vacation homes in Chicago tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The Weather in Chicago

80º 21º
1.43
96º 45º
4.19
95º 52º
7.6
60º -10º
0.91
96º 60º
4
95º 42º
2.32
88º 28º
6.26
53º 18º
2.15
54º 17º
2.51
60º -10º
0.91
66º -1º
4.39
60º -10º
0.91
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Rainy days
This climate histogram shows you the weather patterns in Chicago. The warmest months in Chicago are August and May, when temperatures reach 96 ˚F. The coolest month is January, when temperatures drop to -10 ˚F. The wettest month in Chicago is June with 7.6 inches of rain, while the driest month is January with 0.91 inches of rain.

What Expert Travelers Think

Vacation Rentals in Chicago

At AllTheRooms.com we have accommodations from all of your favourite providers - Airbnb, VRBO, priceline and more. AllTheRooms has 4,863 vacation rentals, hotels and other great places to stay during your time in Chicago, with everything from cheap hostels and homestays to luxury Airbnbs and hotels. For those trying to keep costs down, the lowest priced place to stay in Chicago comes in at $8.12 per night. The average price of accommodation in is $158 per night.

If you want to stay connected during your trip, then you can choose from over 2,432 accommodations in Chicago that have WiFi. 330 of our accommodations in include a breakfast in the price. You can keep up with your workout regime by staying at one of 321 accommodations that provide gym facilities. If you are driving to Chicago, you'll want to pick from 1,942 places to stay that provide parking. 159 hotels and vacation rentals have a pool or jacuzzi.

AllTheRooms has 433 pet-friendly places to stay in Chicago, so if you're travelling with your cat or dog you won't have any trouble.

We combine a wide variety of Chicago accommodations including vacation rentals, homestays, hostels and other unique places to stay into one easy search. We show results from more than 7 providers, including 2,114 places to stay from Airbnb, 129 accommodations from VRBO and 103 places to stay from priceline.

3,501 of our accommodations in Chicago have been reviewed and rated. 92% are rated excellent or good. 974 accommodations allow instant booking.