Chicago Vacation Rentals

Our Favorite Vacation Rentals in Chicago

  • Homewood Suites By Hilton Chicago Downtown South Loop
    Good196br 3-star Home/Apartment
    Booking.com
    From
    $184
  • Brand New Garden Level Room in Chicago
     Home/Apartment
    HolidayLettings
    From
    $37
  • West-Loop Apartments by Cloud9
     Home/Apartment
    Booking.com
    From
    $167
  • Dorothy's Place
     3br Home/Apartment
    HolidayLettings
    From
    $200
  • Ginosi 747 Apartel
     22br Home/Apartment
    Booking.com
    From
    $46
  • Contemporart Celebrity themed private parking runs to downtown
     2br Home/Apartment
    HolidayLettings
    From
    $211
  • Gorgeous 2BR/2BA Apt near Shedd Aquarium by Domio!
     Home/Apartment
    Booking.com
    From
    $227
  • Oak Park Beauty Sleeps 1 to 8 Guests
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $218

Check prices for these upcoming dates

Chicago Vacation Rentals with a Pool

  • Luxury Apartment 2BR 2BA Highrise/Millenimun Park
    Excellent2br Home/Apartment
    Airbnb
    From
    $463
  • Domio | Loop | Vibrant 2BR/2.5BA Apt + Pool and Fitness Center
    Good2br Home/Apartment
    Airbnb
    From
    $276
  • Peaceful South Loop Retreat Near DOWNTOWN Chicago!
    ExcellentHome/Apartment
    Airbnb
    From
    $141

Chicago Vacation Rentals with Wi-Fi

  • SHARED Artist Loft . Very Unique
    Excellent2br Home/Apartment
    Airbnb
    From
    $102
  • Nice DowntownApartment great view perfect location
    ExcellentHome/Apartment
    Airbnb
    From
    $168
  • Sonder | Greektown Suites | Airy 3BR + Rooftop
    Excellent3br Home/Apartment
    Airbnb
    From
    $256
  • Domio | Loop | 2 BR Duplex + Fitness Center
     2br Home/Apartment
    Airbnb
    From
    $241

Chicago Pet-Friendly Vacation Rentals

  • Luxe Chicago Townhome w/ Balcony - 20 Mins to DT!
     2br Home/Apartment
    HolidayLettings
    From
    $235
  • Beautiful Room in Chicago
     Home/Apartment
    HolidayLettings
    From
    $37
  • South Loop Cozy 2BdRm parking&WiFi&NetFlix
    Nice2br Home/Apartment
    Airbnb
    From
    $99
  • Vintage Storefront on 18th Street
    ExcellentHome/Apartment
    Airbnb
    From
    $97

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.

Events

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.

Nightlife

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

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 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
51°
2
65° -2°
2
80° 27°
6
83° 42°
8
91° 51°
3
97° 62°
4
91° 60°
4
91° 57°
8
88° 26°
5
58°
1
62° 13°
1
55° -22°
1
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Rainy days

This climate histogram shows you the weather patterns in Chicago. The hottest month in Chicago is June, when temperatures peak at 97 ˚F. The coolest month is December, when temperatures drop to -22 ˚F. The wettest month in Chicago is August with 7.6 inches of rain, while the driest month is December with 1.1 inches of rain.

What Expert Travelers Think

  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen

Vacation Rentals in Chicago

At AllTheRooms.com we have vacation rentals from all of your favorite providers - Airbnb, Priceline, Agoda and others. We have 4,209 vacation rentals, hotels and other accommodation types in Chicago ranging from low-cost options to luxury places to stay. When traveling on a budget, the cheapest place to stay in Chicago is available at $10 per night. In general, a place to stay in Chicago will cost you $164 per night.

If you would like to stay connected during your vacation, then you can choose from over 1,986 accommodations in Chicago that have WiFi. 275 places to stay include a morning meal. You can keep up with your workout regime by staying at one of 284 accommodations that provide gym facilities. Driving to Chicago? Then choose one of the 1,702 places to stay that comes with a parking spot included. 152 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 331 pet-friendly accommodations available.

In Chicago AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 5 providers, including 1,880 places to stay from Airbnb, 80 accommodations from Priceline and 80 places to stay from Agoda.

3,037 of the rentals in Chicago have been rated by previous guests. They rated 93% as great. You can instantly book any of 786 places to stay right now.

Destinations near Chicago

  • Galena1,132 Properties
  • Springfield567 Properties
  • Champaign565 Properties
  • Evanston411 Properties
  • Naperville404 Properties
  • Peoria398 Properties
  • Schaumburg385 Properties
  • Rockford379 Properties
  • Bloomington341 Properties
  • Marion327 Properties
  • Urbana310 Properties
  • Rosemont301 Properties
  • Carbondale289 Properties
  • Oak Park239 Properties
  • Aurora176 Properties
  • Joliet152 Properties
  • Rock Island152 Properties
  • Nauvoo151 Properties
  • Moline85 Properties
  • Effingham54 Properties
  • Fox Lake32 Properties