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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.

Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room · 2 guests · 1 bed · 1 shared bath
Stylish, Cozy Apartment for the Perfect Get Away

This amazing apartment is located in the Little Village community in Chicago. Little Village is the heart of the Mexican community because it's vivid representation of the Mexican culture. In addition, the apartment is close to two Chicago parks where you can enjoy a walk or a bike ride.

What guests are saying:

“Paul’s place was beautiful! My husband and I loved the neighborhood, and had a wonderful stay. Everything was exceptional. Can’t wait to stay again next time we return to Chicago! We miss our feline friend Abu already!”

Room with private bathroom
Private room · 1 guest · 1 bath
Room with private bathroom

The unit is near Blue Line Train station,young people after work pubs, Supermarkets. and restaurants.

What guests are saying:

“Rebecca is a very kind, sweet and thoughtful hostess. I was able to meet her in person because my daughter and I were 4 hours early upon checking in. She graciously welcomed us in. She also gave us tips on the local restaurants and the best way to get around Chicago. I would definitely stay here again!”

Logan Square Lookout
SUPERHOSTEntire apartment · 4 guests · 2 beds · 1 bath
Logan Square Lookout

Great top floor apartment along a tree lined street with free street parking. Has a cozy small bedroom with a spacious living room and kitchen. On Site Coin operated laundry. Great back yard with garden area. This is in the super nice Logan Square neighborhood with cool bars and award winning restaurants. Friendly safe neighborhood with lots to do. Quick walk to the Blue Line gets you Downtown or out to O'Hare. I own the building which consists of 3 apartments. So I'm always nearby.

What guests are saying:

“Great stay in Logan Square! Free and easy parking on the street, plus only a 10 minute walk from the Blue Line for easy and convenient transportation around the city. Spacious top floor apartment on a quiet street. Definitely recommend eating at Lula Cafe (only a 10 minute walk) while you’re there!”

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

Sanitized, Disinfected, Highly-Clean Old Town Rowhouse
PLUSEntire house
Sanitized, Disinfected, Highly-Clean Old Town Rowhouse
Price:$193 / night
Cozy Home and Garden
SUPERHOSTEntire house
Cozy Home and Garden
Price:$60 / night
Cozy garden apartment historic Jackson Bvld.
SUPERHOSTEntire house
Cozy garden apartment historic Jackson Bvld.
Price:$136 / night
★SPACIOUS 4-LEVEL TOWNHOUSE★CLOSE TO EVERYTHING★
SUPERHOSTEntire house
★SPACIOUS 4-LEVEL TOWNHOUSE★CLOSE TO EVERYTHING★
Price:$599 / night
ENTIRE CITY ROW HOUSE  WITH 2 CAR PARKING & YARD
SUPERHOSTEntire house
ENTIRE CITY ROW HOUSE WITH 2 CAR PARKING & YARD
Price:$94 / night
Gorgeous Humboldt Park Flat
Entire house
Gorgeous Humboldt Park Flat
Price:$90 / night
Sunny Character-Filled Apartment in Trendy Ukrainian Village
PLUSEntire house
Sunny Character-Filled Apartment in Trendy Ukrainian Village
Price:$69 / night
Amazing Penthouse Skyline Views!
Entire house
Amazing Penthouse Skyline Views!
Price:$349 / night
Classic Chicago (entire ) 3 bed Row HousePARK FREE
SUPERHOSTEntire house
Classic Chicago (entire ) 3 bed Row HousePARK FREE
Price:$88 / night
Feel at Home in Chicago, with Parking, Steps from Evanston
PLUSEntire house
Feel at Home in Chicago, with Parking, Steps from Evanston
Price:$86 / night
Lakeview | Great for long-term stays, WFH option
SUPERHOSTEntire house
Lakeview | Great for long-term stays, WFH option
Price:$142 / night
Charming 2BR on Quiet Street Close to the Action
SUPERHOSTEntire house
Charming 2BR on Quiet Street Close to the Action
Price:$230 / night
Show all

Pet-friendly apartments

Best in Chicago, private, amazing garden space
SUPERHOSTEntire apartment
Best in Chicago, private, amazing garden space
Price:$146 / night
Chicago Modern Studio in High Rise building
Entire apartment
Chicago Modern Studio in High Rise building
Price:$50 / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:$88 / night
Large High-Class Apt Near Beach w/ Free Parking!
SUPERHOSTEntire apartment
Large High-Class Apt Near Beach w/ Free Parking!
Price:$169 / night
Heart of Wicker Park Bright 1st Story Walk-Up!
SUPERHOSTPrivate room
Heart of Wicker Park Bright 1st Story Walk-Up!
Price:$30 / night
PANORAMIC SKYLINE VIEWS At Your Luxury Studio Loft
SUPERHOSTEntire apartment
PANORAMIC SKYLINE VIEWS At Your Luxury Studio Loft
Price:$90 / night
Ukrainian Village Garden Retreat
Entire apartment
Ukrainian Village Garden Retreat
Price:$88 / night
Palos Hills Apartment with a View
SUPERHOSTEntire apartment
Palos Hills Apartment with a View
Price:$90 / night
MODERN LOFT Downtown by McCormick w/KING BED WiFi
SUPERHOSTEntire apartment
MODERN LOFT Downtown by McCormick w/KING BED WiFi
Price:$21 / night
Andersonville’s best location, near Aragon, w/prkg
SUPERHOSTEntire apartment
Andersonville’s best location, near Aragon, w/prkg
Price:$132 / night
Bright family-friendly Lincoln Square 2-bed 1-bath
SUPERHOSTEntire apartment
Bright family-friendly Lincoln Square 2-bed 1-bath
Price:$98 / night
The Hobbit Hole
SUPERHOSTEntire apartment
The Hobbit Hole
Price:$51 / night
Show all

Apartments with WiFi

Stylish, Cozy Apartment for the Perfect Get Away
SUPERHOSTPrivate room
Stylish, Cozy Apartment for the Perfect Get Away
Price:$14 / night
Room with private bathroom
Private room
Room with private bathroom
Price:$22 / night
Explore Chicago from an Urban Sanctuary with Free Parking
PLUSEntire apartment
Explore Chicago from an Urban Sanctuary with Free Parking
Price:$61 / night
Logan Square Lookout
SUPERHOSTEntire apartment
Logan Square Lookout
Price:$48 / night
Small Sleeper sofa in eclectic living room.
SUPERHOSTShared room
Small Sleeper sofa in eclectic living room.
Price:$27 / night
Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire apartment
Hip Chicago Apartment - FREE Parking Spot Included
Price:$64 / night
Cosmopolitan nest in Oak Parks North Side
SUPERHOSTEntire apartment
Cosmopolitan nest in Oak Parks North Side
Price:$50 / night
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
SUPERHOSTEntire apartment
LUX 1BR/1BA Top-Floor Unobstructed Downtown Views
Price:$116 / night
Best in Chicago, private, amazing garden space
SUPERHOSTEntire apartment
Best in Chicago, private, amazing garden space
Price:$146 / night
Modern and Spacious Guest Suite In Humboldt Park!
SUPERHOSTEntire apartment
Modern and Spacious Guest Suite In Humboldt Park!
Price:$46 / night
Chicago Modern Studio in High Rise building
Entire apartment
Chicago Modern Studio in High Rise building
Price:$50 / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:$88 / 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