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Vacation rental apartments in Chicago

Vacation rental apartments in Chicago

Book downtown vacation rental apartments, houses, and more on Airbnb

Top-rated apartments in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

Best in Chicago, private, amazing garden space
SUPERHOSTEntire apartment · 5 guests · 3 beds · 1 bath
Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness during the Covid-19 pandemic. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 10 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

What guests are saying:

“Upon arrival we had no problem getting a parking space, out front and center which made it super easy to bring our luggage in. Checking in was a breeze, she does have recommendations for food grocery stores etc. if you don’t know the area. We ended up getting delivery from my pi pizza. ( it was decent but was kind of bummed they didn’t deliver the cheesecake and still charged me for it. ) We did stop at Kuma’s corner in Belmont say on the patio and enjoyed a brew with amazing burgers and Mac and cheese. Love this place ! The apartment was cleaned top notch. If you didn’t bring much on your stay there is pretty much everything you need, just bring drinks and snacks. The decor was eclectic and tastefully done. Also being Chicago the fact that they had a nice sitting area amongst their plants and fountain was nice. Several places to sit to enjoy coffee or wine. ( front window, kitchen nook outside on the patio or down low in their yard by the fountain) The yard is shared but they give you privacy if you are enjoying the outside area. The only downside of our trip was the timing, due to covid and some of the recent news happenings we didn’t experience the town as much as wanted, places being closed and safety measures. With that being said no reflection on their place if you plan to visit the area it’s a great apartment. Thank you for the stay best wishes to you.”

Modern Chicago Loft with a Complimentary Garage Spot
PLUSEntire apartment · 2 guests · 1 bed · 1 bath
Modern Chicago Loft with a Complimentary Garage Spot

Dine by the natural wood breakfast bar or on the rooftop deck. This classy loft boasts open-plan living, exposed brickwork and stunning artwork. Check out our other available listings within the same building by clicking below on our host profile.

What guests are saying:

“This place is really nice. There’s stores near by and very quiet and safe. The hosts are available all the time. I was having issues with my WiFi, but I was able to text them and get it fixed right away. If I ever go back, I will definitely look into this place again.”

Explore Chicago from an Urban Sanctuary with Free Parking
PLUSEntire apartment · 2 guests · 1 bed · 1 bath
Explore Chicago from an Urban Sanctuary with Free Parking

The apartment has been artfully redesigned with a love for the past. Quirky vintage items complement reclaimed wood furnishings to create a sense of character and warmth. Take a seat atop a House of Blues bar stool as you enjoy your morning coffee.

What guests are saying:

“What a great little place! It's clean and old-fashioned yet modern at the same time... e.g,. the fridge & microwave/oven, which were super cool. Lots of thought and care apparent in each detail, from the floors (hardwood, tile, pebbles in shower) to the decorating. Clean and simple yet unique. Small but well-appointed & had everything I needed. Julia, my contact, was very welcoming. Thank you!”

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Popular apartment amenities in Chicago

  • Wifi
  • Kitchen
  • Air conditioning
  • Free parking
  • Heating

Houses in Chicago

Feel at Home in Chicago, with Parking, Steps from Evanston
PLUSEntire house
Feel at Home in Chicago, with Parking, Steps from Evanston
Price:R1,554 ZAR / night
★SPACIOUS 4-LEVEL TOWNHOUSE★CLOSE TO EVERYTHING★
SUPERHOSTEntire house
★SPACIOUS 4-LEVEL TOWNHOUSE★CLOSE TO EVERYTHING★
Price:R10,525 ZAR / night
ENTIRE CITY ROW HOUSE  WITH 2 CAR PARKING & YARD
SUPERHOSTEntire house
ENTIRE CITY ROW HOUSE WITH 2 CAR PARKING & YARD
Price:R1,534 ZAR / night
Amazing Penthouse Skyline Views!
Entire house
Amazing Penthouse Skyline Views!
Price:R6,137 ZAR / night
Classy and Cozy home in Evanston
SUPERHOSTPrivate room
Classy and Cozy home in Evanston
Price:R1,406 ZAR / night
Spacious home 5BR/2BH, 10 min downtown w/parking
PLUSEntire house
Spacious home 5BR/2BH, 10 min downtown w/parking
Price:R6,885 ZAR / night
Super Cozy Bed/Bath in Awesome Andersonville Home!
SUPERHOSTPrivate room
Super Cozy Bed/Bath in Awesome Andersonville Home!
Price:R791 ZAR / night
Cozy garden apartment historic Jackson Bvld.
SUPERHOSTEntire house
Cozy garden apartment historic Jackson Bvld.
Price:R2,384 ZAR / night
Classic Chicago (entire ) 3 bed Row HousePARK FREE
SUPERHOSTEntire house
Classic Chicago (entire ) 3 bed Row HousePARK FREE
Price:R1,564 ZAR / night
The Green Line House near  United Center Downtown
SUPERHOSTEntire house
The Green Line House near United Center Downtown
Price:R2,314 ZAR / night
Fresh and Sunny Bed & Bath by UofC
SUPERHOSTPrivate room
Fresh and Sunny Bed & Bath by UofC
Price:R1,220 ZAR / night
Classy and Cozy 2nd. Room
SUPERHOSTPrivate room
Classy and Cozy 2nd. Room
Price:R1,180 ZAR / night
Show all

Pet-friendly apartments

Best in Chicago, private, amazing garden space
SUPERHOSTEntire apartment
Best in Chicago, private, amazing garden space
Price:R2,636 ZAR / night
Checkerboard Studio with Private Outdoor Hot Tub and Yard
PLUSEntire apartment
Checkerboard Studio with Private Outdoor Hot Tub and Yard
Price:R2,558 ZAR / night
Great Place Garfield Park 3 Bedroom
SUPERHOSTEntire apartment
Great Place Garfield Park 3 Bedroom
Price:R934 ZAR / night
Stunning Chicago Loft Near Wrigley Field
Entire apartment
Stunning Chicago Loft Near Wrigley Field
Price:R1,991 ZAR / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:R1,541 ZAR / night
"Home Away from Home" - Free Street Parking!
SUPERHOSTEntire apartment
"Home Away from Home" - Free Street Parking!
Price:R1,493 ZAR / night
Walk to Little Italy from a Placid Townhouse Apartment
PLUSEntire apartment
Walk to Little Italy from a Placid Townhouse Apartment
Price:R1,945 ZAR / night
River North's Rock N Roll - Covd Safer, No Common Areas
PLUSEntire apartment
River North's Rock N Roll - Covd Safer, No Common Areas
Price:R5,267 ZAR / night
Relaxed Bucktown/Wicker Park 1B Apt
SUPERHOSTEntire apartment
Relaxed Bucktown/Wicker Park 1B Apt
Price:R1,381 ZAR / night
Large High-Class Apt Near Beach w/ Free Parking!
SUPERHOSTEntire apartment
Large High-Class Apt Near Beach w/ Free Parking!
Price:R3,020 ZAR / night
Kasa | Chicago | Premiere 2BD/2BA South Loop Apartment
SUPERHOSTEntire apartment
Kasa | Chicago | Premiere 2BD/2BA South Loop Apartment
Price:R3,165 ZAR / night
Fully Furnished Apartment Wicker Park Free Parking
SUPERHOSTEntire apartment
Fully Furnished Apartment Wicker Park Free Parking
Price:R1,727 ZAR / night
Show all

Apartments with WiFi

Best in Chicago, private, amazing garden space
SUPERHOSTEntire apartment
Best in Chicago, private, amazing garden space
Price:R2,636 ZAR / night
Modern Chicago Loft with a Complimentary Garage Spot
PLUSEntire apartment
Modern Chicago Loft with a Complimentary Garage Spot
Price:R1,305 ZAR / night
Explore Chicago from an Urban Sanctuary with Free Parking
PLUSEntire apartment
Explore Chicago from an Urban Sanctuary with Free Parking
Price:R1,130 ZAR / night
Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire apartment
Hip Chicago Apartment - FREE Parking Spot Included
Price:R1,079 ZAR / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire apartment
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:R2,226 ZAR / night
Enjoy Chicago’s Nightlife from Studio Apartment
PLUSEntire apartment
Enjoy Chicago’s Nightlife from Studio Apartment
Price:R1,180 ZAR / night
Cozy and Stylish Studio with Free Parking in Irving Park
PLUSEntire apartment
Cozy and Stylish Studio with Free Parking in Irving Park
Price:R929 ZAR / night
Walk to Lake Michigan From a Contemporary Uptown Haven
PLUSEntire apartment
Walk to Lake Michigan From a Contemporary Uptown Haven
Price:R979 ZAR / night
Basement Studio w/Free St. Parking, Humboldt Park
SUPERHOSTEntire apartment
Basement Studio w/Free St. Parking, Humboldt Park
Price:R791 ZAR / night
Checkerboard Studio with Private Outdoor Hot Tub and Yard
PLUSEntire apartment
Checkerboard Studio with Private Outdoor Hot Tub and Yard
Price:R2,558 ZAR / night
Stunning Retro Apartment in Andersonville
PLUSEntire apartment
Stunning Retro Apartment in Andersonville
Price:R1,591 ZAR / night
Sonder | Spacious 1BR in South Loop Near Trader Joe's
Entire apartment
Sonder | Spacious 1BR in South Loop Near Trader Joe's
Price:R5,623 ZAR / night
Show all

Learn more about Chicago

What types of vacation rentals are available in Chicago?

Here in Chicago, there are plenty of options for places to stay. Here are a few examples:
  • Apartments (4,696 rentals)
  • Houses (1,150 rentals)
  • Guest suites (242 rentals)

Are there apartments with WiFi?

Who doesn’t want WiFi in their apartment? Here in Chicago, you’ll find 4,531 apartments that have WiFi.

What area should I stay in when traveling to Chicago?

Every area of Chicago is unique. So where should you stay? Let the locals help you decide. These are their top recommendations:
  • Lakeview (418 rentals)
  • Logan Square (340 rentals)
  • River North (325 rentals)
  • Loop (306 rentals)
  • Lincoln Park (258 rentals)

What are the top attractions in Chicago?

Locals agree that these attractions are worth a visit:
  • The Art Institute of Chicago (363 rentals)
  • Lincoln Park (138 rentals)
  • Wrigley Field (750 rentals)
  • Navy Pier (99 rentals)
  • Field Museum of Natural History (144 rentals)

What are some kid-friendly activities in Chicago?

Locals agree—these are all great places to take the kids:
  • Lincoln Park
  • Wrigley Field
  • Shedd Aquarium
  • Field Museum of Natural History
  • Museum of Science and Industry

What are the top places to eat in Chicago?

Whether you’re looking for a tasty treat or a hearty meal, here’s where the locals say to go:
  • Big Star
  • Longman & Eagle
  • Revolution Brewing
  • Parson's Chicken & Fish
  • Au Cheval