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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:

“This is a gold mine as far as it comes to somewhere to stay in the Chicago area. Not only is it great value but also in a great location. You can tell the neighbors respect other neighbors and proud to have a clean thriving neighborhood. Super stylish and clean place to stay. And of course, the cat will make your heart melt. Such a sweetie, lol.”

Cozy guest room 1 block from U of C
SUPERHOSTPrivate room · 2 guests · 1 bed · 1 shared bath
Cozy guest room 1 block from U of C

Cozy guest room with office desk and futon. Kitchen and living room are available for guest(s) to use. 1 block from University of Chicago, 15 minutes from downtown, 2 blocks from Metra, 4 blocks from Lake Shore Drive and CTA Green Line train. Nearby historic Hyde Park area. Grocery store Jewel-Osco is within walking distance. Parking is street parking 1/2 block away from the apartment. Host lives at listing.

What guests are saying:

“Darren was a fantastic host! He always responded to messages very quickly (even late at night, wow), and he went way out of his way to make sure that everything was good for us at his place. He even hand wrote a quick reference sheet to help us remember details about wifi/how to unlock the doors, remembered that we were there celebrating a birthday, and made things a little extra special. Darren's house was impeccably clean! It's clear that he's a clean person by nature, and is very driven to make your stay as nice as possible. Very cool guy, thankful we got to meet him. Would highly recommend this place to other travelers, and we will try to stay here again if we can! :)”

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!”

Vacation rentals for every style

Get the amount of space that is right for you

  • Apartments
  • Houses
  • Guesthouses

Popular apartment amenities in Chicago

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

Houses in Chicago

Self check in self checkout near downtown Chicago
SUPERHOSTPrivate room
Self check in self checkout near downtown Chicago
Price:$32 / night
Quiet Italian Neighborhood, 5 min to downtown
Entire house
Quiet Italian Neighborhood, 5 min to downtown
Price:$64 / night
Perfect Oasis 4mins walk to University & hospital
Private room
Perfect Oasis 4mins walk to University & hospital
Price:$36 / night
Bridgeport Prime Location 5min from downtown R2
SUPERHOSTPrivate room
Bridgeport Prime Location 5min from downtown R2
Price:$32 / night
Little Farm in the City Back Bedroom
SUPERHOSTPrivate room
Little Farm in the City Back Bedroom
Price:$30 / night
Sunny Attic Suite at Casa de Ninners
PLUSPrivate room
Sunny Attic Suite at Casa de Ninners
Price:$38 / night
The Peacock: 19th Century Swank
Entire house
The Peacock: 19th Century Swank
Price:$108 / night
Room for solo traveler near midway airport.
SUPERHOSTPrivate room
Room for solo traveler near midway airport.
Price:$29 / night
Catmandu 2
SUPERHOSTPrivate room
Catmandu 2
Price:$40 / night
Your Fantastic Futon! 1st Floor TV room with locks
Private room
Your Fantastic Futon! 1st Floor TV room with locks
Price:$23 / night
Warm Southern Exposure Sleeping Room
SUPERHOSTPrivate room
Warm Southern Exposure Sleeping Room
Price:$27 / night
Cozy room in a Charming Coach House
SUPERHOSTPrivate room
Cozy room in a Charming Coach House
Price:$42 / night
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Pet-friendly apartments

Bright family-friendly Lincoln Square 2-bed 1-bath
SUPERHOSTEntire apartment
Bright family-friendly Lincoln Square 2-bed 1-bath
Price:$95 / night
Large High-Class Apt Near Beach w/ Free Parking!
SUPERHOSTEntire apartment
Large High-Class Apt Near Beach w/ Free Parking!
Price:$198 / night
⭐️Luxury Suite w Gym & Parking by Dtwn Evanston⭐️
SUPERHOSTEntire apartment
⭐️Luxury Suite w Gym & Parking by Dtwn Evanston⭐️
Price:$76 / night
Palos Hills Apartment with a View
SUPERHOSTEntire apartment
Palos Hills Apartment with a View
Price:$89 / night
Spacious smart apartment with theater & jacuzzi.
Entire apartment
Spacious smart apartment with theater & jacuzzi.
Price:$49 / night
Casa de Sueño 4.9 Star/Private/Near Train/Loyola
SUPERHOSTPrivate room
Casa de Sueño 4.9 Star/Private/Near Train/Loyola
Price:$38 / night
The Hobbit Hole
Entire apartment
The Hobbit Hole
Price:$51 / night
Humboldt Hide Away
SUPERHOSTEntire apartment
Humboldt Hide Away
Price:$85 / night
Andersonville Living
SUPERHOSTEntire apartment
Andersonville Living
Price:$99 / night
Great location.
SUPERHOSTEntire apartment
Great location.
Price:$87 / night
Comfortable Irving Park Apartment
SUPERHOSTEntire apartment
Comfortable Irving Park Apartment
Price:$75 / night
Fully Furnished Apartment Wicker Park Free Parking
SUPERHOSTEntire apartment
Fully Furnished Apartment Wicker Park Free Parking
Price:$99 / night
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Apartments with WiFi

Visit the United Center & Explore City of Chicago
SUPERHOSTEntire apartment
Visit the United Center & Explore City of Chicago
Price:$50 / night
Convenient location!
Private room
Convenient location!
Price:$27 / night
Hattie’s House
Private room
Hattie’s House
Price:$36 / night
Cozy and Stylish Studio with Free Parking in Irving Park
PLUSEntire apartment
Cozy and Stylish Studio with Free Parking in Irving Park
Price:$67 / night
Treelined Vintage Private 1BR in Lincoln Park
Private room
Treelined Vintage Private 1BR in Lincoln Park
Price:$41 / night
Cosmopolitan nest in Oak Parks North Side
SUPERHOSTEntire apartment
Cosmopolitan nest in Oak Parks North Side
Price:$54 / night
Private room, shared apartment, easy city access.
SUPERHOSTPrivate room
Private room, shared apartment, easy city access.
Price:$43 / night
Entire Condo near Univ. of Chicago
Entire apartment
Entire Condo near Univ. of Chicago
Price:$60 / night
7 STAR THE MALIA OASIS #2 3BR/1.5ba + Office Space
SUPERHOSTEntire apartment
7 STAR THE MALIA OASIS #2 3BR/1.5ba + Office Space
Price:$43 / night
Wicker Park: Newly-Furnished Nest Close To It All!
Private room
Wicker Park: Newly-Furnished Nest Close To It All!
Price:$35 / night
G3. Next to Downtown! Best location & affordable!
SUPERHOSTPrivate room
G3. Next to Downtown! Best location & affordable!
Price:$36 / night
Chicago chinatown great location(B) (中文房东)
SUPERHOSTPrivate room
Chicago chinatown great location(B) (中文房东)
Price:$39 / night
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Nearby destinations