We use cookies to provide you with the best browsing experience. The data collected by cookies is used to optimise the website for our users and deliver an appropriate service and relevant information to you. By using our site we assume you’re aware and agree to use the cookies for this purpose.

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 Index in Chicago

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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

65º -3º
0.17
60º
2.71
70º 14º
2.4
82º 17º
4.19
82º 33º
6.27
89º 38º
3.77
95º 54º
2.6
92º 58º
4.23
92º 53º
1.9
95º 50º
0.56
60º
2.71
62º 20º
2.33
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Rainy days
Powered by:

This climate histogram shows you the weather patterns in Chicago. The hottest month in Chicago is July, when temperatures peak at 95 ˚F. The coolest month is December, when temperatures drop to -3 ˚F. The wettest month in Chicago is April with 6.27 inches of rain, while the driest month is December with 0.17 inches of rain.

Vacation Rentals in Chicago

At AllTheRooms.com we have accommodations from all of your favourite providers - Airbnb, VRBO, priceline and more. We have 19960 vacation rentals, hotels and other accommodation types in Chicago ranging from budget options to luxury places to stay. For those traveling on a budget, the cheapest place to stay in Chicago is available at $6.25 per night. The average price of accommodation in is $154 per night.

If you want to stay connected during your trip, then you can choose from over 5112 accommodations in Chicago that have WiFi. 700 of our accommodations in include a breakfast in the price. You can keep up with your workout regime by staying at one of 646 accommodations that provide gym facilities. If you are driving to Chicago, you'll want to pick from 4068 places to stay that provide parking. 304 accommodations come with a pool or jacuzzi

If you're traveling with a furry friend, then be sure to choose one of the 920 pet-friendly accommodations available.

AllTheRooms aggregates vacation rentals, hotels and other unique accommodation types from 7 providers in Chicago, including 4438 places to stay from Airbnb, 288 accommodations from VRBO and 206 places to stay from priceline

14492 of our places to stay in Chicago have been rated by previous guests. They rated 92% as excellent or good. 4100 accommodations allow instant booking.

Our providers