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Apartment holiday rentals in Woodlawn, Chicago

Find and book unique apartments on Airbnb

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Popular amenities for Woodlawn, Chicago apartment rentals

Weekly apartment rentals

Guest favourite
Flat in Woodlawn
5 out of 5 average rating, 8 reviews

Charming 2-bdrm near University of CHI Campus

BisratRating, 5 stars2 weeks ago
This was a great stay! The place was in a great location - not too far from downtown but in a peaceful neighborhood. Super comfortable and convenient. Would definitely stay here again!
Flat in Woodlawn
4.79 out of 5 average rating, 107 reviews

The Woodlawn Grey - Large 3bd/3ba Apt by UChicago

MichelleRating, 5 stars3 weeks ago
We came to Chicago so that I could attend a workshop at the university. I brought along my partner and teenage son, so Latrice's apartment was a perfect fit for us, offering plenty of space and privacy within walking distance to campus. There was a lot of natural light in the living room, but dark curtains in the bedrooms to keep out the early morning sun. It's not fancy, but everything was clean and in good condition. The kitchen was well stocked with appliances and cookware, and we enjoyed the coffee that Latrice provided for us. Excellent value for money!
Guest favourite
Flat in Pilsen Historic District
4.94 out of 5 average rating, 51 reviews

Pilsen Modern Chic Retreat

ElinorRating, 5 stars4 days ago
Great stay, carmen was very responsive and the place is very modern and clean.
Top guest favourite
Flat in Hickory Hills
4.96 out of 5 average rating, 46 reviews

Cozy Guest Suite. Private Entry+ Turo Rental

SusanRating, 5 stars4 days ago
Five star stay all around. Great location, near a nature reserve. Large living room and bedroom, lots of amenities. Cornell supplied excellent directions and instructions. Super easy to communicate with. Thoroughly enjoy the stay. Would love to book again, but calendar is full and I know why - this please is great, Thank you Cornell!
Flat in Woodlawn
4.82 out of 5 average rating, 176 reviews

University Retreat

libbieRating, 5 stars1 month ago
Very nice place to stay. Michael was a great host. area is walkable, within 1 mile of university of Chicago, museum of science and industry and South shore/metra.
Guest favourite
Flat in Chicago
4.82 out of 5 average rating, 22 reviews

Apartment in Chicago

CrisyRating, 5 stars2 weeks ago
amazing place! clean and quiet! would definitely stay again. 💚 a little ways from the city but it’s p good :)
Guest favourite
Flat in Washington Park
4.94 out of 5 average rating, 66 reviews

*Big Blue* Eclectic 3bdrm/1bath Bronzeville Gem

DorothyRating, 5 stars3 weeks ago
Saskya’s place was immaculate. Exactly as described. They were a very friendly and responsive host. I would definitely stay again.
Guest favourite
Flat in Chicago
4.9 out of 5 average rating, 20 reviews

Comfortable 1 BR , South Side Chgo, 1st Floor

Collier.KathyRating, 5 stars1 week ago
Michelle's place was just as she described it. The positive reviews were just as they stated. It was a great place to stay and in the very vicinity that I was visiting. It was peaceful and a home away from home. I will definitely look to see if her listing is available if I visit again. Michelle, thank you for everything. We enjoy it!!!

Private apartment rentals

Guest favourite
Flat in Hyde Park
4.94 out of 5 average rating, 525 reviews

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

JoelRating, 5 stars1 week ago
Over the last 3-4 years we have stayed at Ian’s at least 10 times while visiting our son at Uchicago for football games and graduations. It is a very clean and welcoming place to stay. We have enjoyed this Airbnb so much we have recommended it to underclassmen families to use and keep up our tradition. Ian has been more than accommodating for us to book and has responded very promptly when asked for favors. Overall, I would give it a 10/10!
Guest favourite
Flat in Woodlawn
4.83 out of 5 average rating, 127 reviews

Tones' Comfort Stay. Near UofChgo/15min frm Dntown

AnaRating, 5 stars2 weeks ago
Large, clean, and cozy space. The neighborhood was very nice and quiet. We had access to a grocery store just a couple blocks away. It was easy to catch an uber wherever we needed. Host was very communicative and sent us local recommendations for our stay. It was perfect for our weekend trip. ☺️
Top guest favourite
Flat in Blue Island
4.94 out of 5 average rating, 299 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

KatharynRating, 5 stars1 week ago
Charming Victorian house in a peaceful and safe neighbourhood. So thankful for the really comfy queen bed - felt like my home mattress!
Guest favourite
Flat in Avondale
4.97 out of 5 average rating, 162 reviews

Designer Avondale Attic

JaninaRating, 5 stars2 weeks ago
Einfach nur wundervoll. Das war eine der schönsten Unterkünfte, in der ich je war. Die Wohnung ist total liebevoll eingerichtet. Alles war super sauber und ordentlich. Es gibt sogar Zahnbürsten, Zahnpasta und eine Schlafmaske, falls man sie benötigt. Die Küche ist auch super ausgestattet mit allem was man braucht. Der kurze Weg zur Metro war ebenfalls sehr praktisch. Wir würden definitiv wieder kommen.
Guest favourite
Flat in Lake View
4.94 out of 5 average rating, 109 reviews

Costa Lota Near Wrigley

ToddRating, 5 stars5 days ago
I absolutely loved this place. It was very comfortable and I appreciated all the little design touches. I loved the seperate entrace from the rest of the building. It was a very Chicago apartment. I felt right at home. The water pressure was great and appreciated having a sound machine in the bedroom. Special shout out to the character drinking glasses. The location was perfect right off Ashland and close to Clark. I would love to stay here again sometime.
Superhost
Flat in Bronzeville
4.9 out of 5 average rating, 107 reviews

Chicago Themed Garden Unit - Historic Bronzeville

ArnabRating, 5 stars1 month ago
Kendal is a superhost. The apartment is as described. Enjoyed staying at this apartment. Very near to supermarkets, McCormick convention centre and public transport. Highly recommend.
Guest favourite
Flat in McKinley Park
4.86 out of 5 average rating, 313 reviews

Charming loft style suite

VivianeRating, 5 stars1 month ago
Joyce foi atenciosa desde o início. o ap está bem.localizado, limpo e com todas as facilidades detalhadas são anúncio. Recomendo!
Top guest favourite
Flat in Chicago
4.98 out of 5 average rating, 153 reviews

Bronzeville Hidden Oasis

AmandaRating, 5 stars1 week ago
We rented Sherry's place for our son's graduation at University of Chicago. There were 7 of us and we were very comfortable in the unit. It was well appointed and only a 10 minute drive from campus. I would definitely recommend it!

Apartment rentals with a hot tub

Guest favourite
Flat in Logan Square
4.98 out of 5 average rating, 103 reviews

Luxe Ranch & Spa, Euro Opulence, a 4-Season Oasis

BriantRating, 5 stars2 weeks ago
We stayed on the third floor of the complex and enjoyed Matthew's attention to detail. He gave a lot of thought to all components of his property.
Superhost
Flat in West Loop
4.88 out of 5 average rating, 24 reviews

Balance Work,Relaxation&vibrant city life|The Dada

AndreaRating, 5 stars1 month ago
The apartment at 160 north Elizabeth was wonderful! Friendly tenants and staff. Loved it!!!
Top guest favourite
Flat in West Town
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars1 month ago
We stayed with my family for 3 days n loved the place it's ambience, cleanliness, very well equipped with all the necessities.....this place definitely feels like home and the hosts are very kind and quick with there response. Wherever in future I am coming to chicago shall book this place.
Superhost
Flat in Chicago
4.83 out of 5 average rating, 54 reviews

Rooftop HotTub As Seen On "Married At First Sight"

KimikoRating, 5 stars8 months ago
I booked this Air BNB for my girlfriend's birthday weekend and my surprise proposal! Ashlee was very responsive, super helpful, just an overall great host! She went out of her way to decorate the master bedroom for me with rose petals, tea lights, champagne and all! There were snacks in the kitchen, the place was clean and tidy, our group really felt at home! The vibes were everything, and so were the VIEWS from the rooftop!!!! Thank you Ashlee!!
Superhost
Flat in Chicago
4.88 out of 5 average rating, 16 reviews

Large Studio Apartment with no cleaning fee

Latrice Rating, 5 stars1 week ago
David and his co-host were excellent. Our family enjoyed our stay. We used to live in the Bronzeville area and love the new additions to the neighborhood. Everything met or exceeded our expectations.
Superhost
Flat in The Loop
4.69 out of 5 average rating, 49 reviews

Sentral 1 Bedroom Apt in South Loop Chicago

RichardRating, 5 stars1 week ago
Sentral worked great for us going to a graduation for a long weekend. Unit is exactly as described, modern, and clean. Kitchen utensils are reasonable while shelves and refrig are empty save for some coffee so if going to cook/eat be sure to bring everything such as butter, spices, etc. - a Trader Joes is 3 blocks away. Price is not cheap but is very convenient and easy so on balance okay for us. Front desk is very helpful and cheerful.
Superhost
Flat in Chicago
4.79 out of 5 average rating, 19 reviews

Chicago/Beverly/Evergreen Park Home

CarinaRating, 5 stars1 week ago
The host is very helpful. The house next door seems to be abandoned; therefore, there is a lot of trash and broken glass on the floor next to this building. The place is very chic and fun. My favorite part was the bath bar and back yard. There are no dishes only cups and coffee mugs no paper towels and no plates. I liked the fact that the host asked questions before approving our reservation. I will definitely reserve again.
Top guest favourite
Flat in Belmont Cragin
4.98 out of 5 average rating, 119 reviews

Belmont Pleasures - hot tub / arcade gaming room

AustinRating, 5 stars1 week ago
Stay was great and Mariam was a super host. The space was exactly as pictured and all the games were a blast. Miriam even checked in a couple times to make sure we had everything we need and that we were having a good time. For sure would stay here again.

Quick stats about flat rentals in Woodlawn, Chicago

  • Total rentals

    140 properties

  • Total number of reviews

    2K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    130 properties include access to wifi

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