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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.

Modern Chicago Loft with a Complimentary Garage Spot
SUPERHOSTEntire 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:

“The place was super clean. Literally the cleanest airbnb I’ve ever stayed at. Super easy to check in and out. The hosts were also easy to get in contact with and they made sure to check in to see if everything was fine after we arrived. Would definitely stay again!”

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.”

Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire apartment · 4 guests · 2 beds · 1 bath
Hip Chicago Apartment - FREE Parking Spot Included

You’ll love this high-end, newly renovated 2 bedroom apartment located in Chicago’s iconic Logan Square. This bright and modern space has free parking, a fully equipped stainless-steel kitchen and an outdoor sitting area perfect for a sunny meal. Walking distance from a bike rental station and hip Armitage Street where you can find a wide selection of restaurants and bars to suit any palate. You’ll also be close by the 606 Trail, a lovely place to enjoy a walk, bike or go for a run

What guests are saying:

“I really enjoyed my stay at Alex and Leo’s place. Check-in was a breeze, great communication from the hosts, the bed was super comfortable, kitchen had all the necessary items, great TV, and comfy sofa, and the location is excellent with lots of fun places to walk. I highly recommend this place.”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Chicago vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Houses in Chicago

Feel at Home in Chicago, with Parking, Steps from Evanston
SUPERHOSTEntire house
Feel at Home in Chicago, with Parking, Steps from Evanston
Price:$87 / night
★SPACIOUS 4-LEVEL TOWNHOUSE★CLOSE TO EVERYTHING★
SUPERHOSTEntire house
★SPACIOUS 4-LEVEL TOWNHOUSE★CLOSE TO EVERYTHING★
Price:$599 / night
Basement room near Midway Airport
SUPERHOSTPrivate room
Basement room near Midway Airport
Price:$36 / night
A Pilsen Wonderland
SUPERHOSTEntire house
A Pilsen Wonderland
Price:$111 / night
Amazing Penthouse Skyline Views!
Entire house
Amazing Penthouse Skyline Views!
Price:$349 / night
Spacious home 5BR/2BH, 10 min downtown w/parking
SUPERHOSTEntire house
Spacious home 5BR/2BH, 10 min downtown w/parking
Price:$360 / night
Super Cozy Bed/Bath in Awesome Andersonville Home!
SUPERHOSTPrivate room
Super Cozy Bed/Bath in Awesome Andersonville Home!
Price:$45 / night
Cozy garden apartment historic Jackson Bvld.
SUPERHOSTEntire house
Cozy garden apartment historic Jackson Bvld.
Price:$136 / night
Classic Chicago (entire ) 3 bed Row HousePARK FREE
SUPERHOSTEntire house
Classic Chicago (entire ) 3 bed Row HousePARK FREE
Price:$76 / night
❤️Sanitized☕Cozy Retreat❤️Free WiFi & Parking❤️
SUPERHOSTEntire house
❤️Sanitized☕Cozy Retreat❤️Free WiFi & Parking❤️
Price:$100 / night
Fresh and Sunny Bed & Bath by UofC
SUPERHOSTPrivate room
Fresh and Sunny Bed & Bath by UofC
Price:$69 / night
Classy and Cozy 2nd. Room
SUPERHOSTPrivate room
Classy and Cozy 2nd. Room
Price:$67 / night
Show all

Pet-friendly apartments

Best in Chicago, private, amazing garden space
SUPERHOSTEntire apartment
Best in Chicago, private, amazing garden space
Price:$150 / night
Great Place Garfield Park 3 Bedroom
SUPERHOSTEntire apartment
Great Place Garfield Park 3 Bedroom
Price:$35 / night
Stunning Chicago Loft Near Wrigley Field
Entire apartment
Stunning Chicago Loft Near Wrigley Field
Price:$156 / night
Urban Farm Fun!  Walk to Metra/CTA
Entire apartment
Urban Farm Fun! Walk to Metra/CTA
Price:$78 / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:$85 / night
"Home Away from Home" - Free Street Parking!
SUPERHOSTEntire apartment
"Home Away from Home" - Free Street Parking!
Price:$85 / night
River North's Rock N Roll Airbnb
SUPERHOSTEntire apartment
River North's Rock N Roll Airbnb
Price:$300 / night
Relaxed Bucktown/Wicker Park 1B Apt
SUPERHOSTEntire apartment
Relaxed Bucktown/Wicker Park 1B Apt
Price:$96 / night
Large High-Class Apt Near Beach w/ Free Parking!
SUPERHOSTEntire apartment
Large High-Class Apt Near Beach w/ Free Parking!
Price:$186 / night
Kasa | Chicago | Premiere 2BD/2BA South Loop Apartment
SUPERHOSTEntire apartment
Kasa | Chicago | Premiere 2BD/2BA South Loop Apartment
Price:$163 / night
Fully Furnished Apartment Wicker Park Free Parking
SUPERHOSTEntire apartment
Fully Furnished Apartment Wicker Park Free Parking
Price:$98 / night
Andersonville Living
SUPERHOSTEntire apartment
Andersonville Living
Price:$112 / night
Show all

Apartments with WiFi

Modern Chicago Loft with a Complimentary Garage Spot
SUPERHOSTEntire apartment
Modern Chicago Loft with a Complimentary Garage Spot
Price:$67 / night
Best in Chicago, private, amazing garden space
SUPERHOSTEntire apartment
Best in Chicago, private, amazing garden space
Price:$150 / night
Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire apartment
Hip Chicago Apartment - FREE Parking Spot Included
Price:$67 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire apartment
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:$156 / night
Explore Chicago from an Urban Sanctuary with Free Parking
SUPERHOSTEntire apartment
Explore Chicago from an Urban Sanctuary with Free Parking
Price:$61 / night
Enjoy Chicago’s Nightlife from Studio Apartment
SUPERHOSTEntire apartment
Enjoy Chicago’s Nightlife from Studio Apartment
Price:$61 / night
Cozy and Stylish Studio with Free Parking in Irving Park
SUPERHOSTEntire apartment
Cozy and Stylish Studio with Free Parking in Irving Park
Price:$56 / night
Walk to Lake Michigan From a Contemporary Uptown Haven
SUPERHOSTEntire apartment
Walk to Lake Michigan From a Contemporary Uptown Haven
Price:$50 / night
Stunning Retro Apartment in Andersonville
SUPERHOSTEntire apartment
Stunning Retro Apartment in Andersonville
Price:$93 / night
Great Place Garfield Park 3 Bedroom
SUPERHOSTEntire apartment
Great Place Garfield Park 3 Bedroom
Price:$35 / night
Large, Private Logan Square Studio
SUPERHOSTEntire apartment
Large, Private Logan Square Studio
Price:$64 / night
Sonder | Spacious 1BR in South Loop Near Trader Joe's
Entire apartment
Sonder | Spacious 1BR in South Loop Near Trader Joe's
Price:$349 / 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