Chicago Vacation Rentals

Our Favorite Vacation Rentals in Chicago

  • Homewood Suites By Hilton Chicago Downtown South Loop
    Good196br 3-star Home/Apartment
  • Loop and Grant Park - 3 Bedrooms with 2 bathrooms
  • Trendy Apartment with 360 Degree City Views
  • Level Chicago Old Town
     29br Home/Apartment
  • Gorgeous 2BR/2BA Apt near Shedd Aquarium by Domio!
  • Domio I Navy Pier I Central 2BR + Fitness Center
  • Holland Dream - Stunning Duplex by Short Stay
  • Vibrant Studio in Heart of Downtown

Check prices for these upcoming dates

Chicago Vacation Rentals with a Pool

  • McCormick + Stadium | Gym, Pool, W&D | Zencity

Chicago Vacation Rentals with Wi-Fi

  • SHARED Artist Loft . Very Unique
    Excellent2br Home/Apartment
  • Amazing 2BR-2BA in the heart of Downtown Chicago
    Good2br Studio
  • Perfect Location Downtown Apartment Great View
  • Globetrotter Apartment in West Loop

Chicago Pet-Friendly Vacation Rentals

  • South Loop Cozy 2BdRm parking&WiFi&NetFlix
    Nice2br Home/Apartment
  • Stunning Fulton Market-patio- 2 en-suite bathroom
    Good2br Tower
  • Amazing 2-Story Home ★High Ceilings ★Lincoln Park
    Good4br Home/Apartment
  • Sunny & Chic 2 Bed in Red Hot Pilsen!!
    Excellent2br Home/Apartment

Chicago Travel Guide

Getting There

Chicago O’Hare and Chicago Midway are two of the United States’ largest airports; the only thing that could prevent folks from getting to Chicago on a plane would be the weather.

Weather & Climate

The weather in Chicago enjoys well-marked seasons, with summer (June to August) being the most popular time to visit. And we aren’t going to lie to you, winter is frigid, but with the proper layers it could be a good time to come and beat the crowds.

Things to Do & Attractions

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.

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.

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.

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

Where to Stay

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 a great public transport system, it is simple for travelers to get around.


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.

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.


Some of the most well known bars include The Flat Iron, The Owl, and Slippery Slope, whereas major clubs include East Room, Stereo Nightclub, and Society 2201. For fun night out with a healthy dose of nostalgia head to the Emporium Arcade Bar on North Milwaukee Ave (a street that happens to be lined with tons of bars).

Food & Drink

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. Giordano’s is a local classic and easily one of the best places to try traditional Chicago pizza. There are a number of locations throughout the city.

Alinea is one of the best known fine dining experiences in the country, but Girl and the Goat and Boka are just one tier lower, but provide equally tasty, slightly more affordable dishes in an environment that is a bit more laidback.

Art & Culture

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 and the Art Institute of Chicago with its Impressionist and Post-Impressionist works. 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. It is literally impossible to get bored in Chicago.

Family Activities

There is so much to do in Chicago for family 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 Jordan 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.

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 outdoors with the family. The Lurie Gardens, Lincoln Park Zoo and one of Chicago’s lakefront beaches are also picturesque places to spend the afternoon.

Price and Availability in Chicago

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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 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 Weather in Chicago

Rainy days
54° 17°
60° -10°
66° -1°
60° 22°
80° 21°
96° 45°
95° 52°
95° 61°
96° 60°
95° 42°
88° 28°
53° 18°
Rainy days

This climate histogram shows you the weather patterns in Chicago. The hottest month in Chicago is May, when temperatures peak at 96 ˚F. The coolest month is December, when temperatures drop to -10 ˚F. The wettest month in Chicago is July with 7.6 inches of rain, while the driest month is December with 0.91 inches of rain.

What Expert Travelers Think

  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    JazThe Life of a Social Butterfly
  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!


Vacation Rentals in Chicago

Pick the perfect accommodation for your trip at We compare Airbnb, Priceline, Agoda and many more. Chicago has 5,007 hotels, vacation rentals and other special places to stay, with prices to suit careful travellers, extravagant travelers and everything in between. When traveling on a budget, the cheapest place to stay in Chicago is available at $10 per night. An average rental in Chicago costs on average $159 per night.

Those needing to get some work done during their trip to Chicago can choose from 2,323 places to stay that provide WiFi. 315 places to stay include a morning meal. Fitness addicts can get a workout in during their stay by choosing from 310 accommodations that have gym facilities. Driving to Chicago? Then choose one of the 1,930 places to stay that comes with a parking spot included. 165 places to stay have a a pool or jacuzzi

If you're traveling with a furry friend, then make sure to choose one of the 394 pet-friendly accommodations available.

We aggregate vacation rentals, hotels and other unique accommodation types from many providers in Chicago, including 2,212 places to stay from Airbnb, 103 accommodations from Priceline and 80 places to stay from Agoda

3,421 accommodations in Chicago have been reviewed; 92% are rated highly. You can instantly book any of 993 places to stay right now.

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