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Condo holiday rentals in Woodlawn, Chicago

Find and book unique condos on Airbnb

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Popular amenities for Woodlawn, Chicago condo rentals

Weekly condo rentals

Guest favourite
Condo in South Shore
4.97 out of 5 average rating, 29 reviews

Spacious two bedroom condo with a cozy feel!

DanaRating, 5 stars2 weeks ago
The place was very clean and nice! perfect place for a little weekend getaway!
Guest favourite
Condo in Kenwood
4.96 out of 5 average rating, 52 reviews

Beautiful Condo in North Kenwood with Parking

ElizabethRating, 5 stars1 week ago
Lisa was an excellent host. The condo was exactly as represented by photos. Beautifully decorated. All appointments are first rate.
Superhost
Condo in Garfield Ridge
4.84 out of 5 average rating, 19 reviews

1st Floor Condo Apartment Close to Midway Airport

SharliamarRating, 5 stars1 week ago
We enjoyed our stay here. We felt safe and the home was very clean. The kitchen had everything you need if you desire to cook at home. Our host was very accommodating us and allowing us to check in earlier which was extremely helpful! We will definitely come back again!
Guest favourite
Condo in Woodlawn
4.92 out of 5 average rating, 52 reviews

Cozy 3 Bedroom Condo near University of Chicago

KristenRating, 5 stars3 weeks ago
We enjoyed our stay at Iman's place. It was very clean and had the right amount of space for a weekend away from home. The beds were comfortable and we had everything we needed.
Guest favourite
Condo in Wicker Park
4.93 out of 5 average rating, 61 reviews

Luxury Penthouse w/ HOT TUB & Amazing Roof Deck

NatalieRating, 5 stars1 week ago
Our group loved our stay at James's place! This was a last minute back up booking after our first Airbnb was not accurately listed or cleaned, and finding this place made our lives so easy. Flexible late self check in was a breeze and James was totally communicative. Thanks for saving our trip! We would definitely stay again.
Superhost
Condo in Woodlawn
4.72 out of 5 average rating, 104 reviews

Lovely 4-bedroom condo with indoor fireplace

KimRating, 5 stars2 weeks ago
Great space and location for our time in Chicago for our daughter’s UChicago graduation
Superhost
Condo in Chicago
5 out of 5 average rating, 14 reviews

Bronzeville Oasis

RaulRating, 5 stars2 weeks ago
Very nicely furnished…comfortable beds, nice shower/pressure Quiet tranquil place On 3rd floor so with heavy/lots of luggage and bad knees a bit tough
Superhost
Condo in Washington Park
4.78 out of 5 average rating, 49 reviews

Luxury Condo | Karaoke, PS5, SLUSHi & Huge 4K TV’s

DelashondaRating, 5 stars1 day ago
Brain, was a 5 star host their was not a time i reached out to him and he didn't respond. This condo was very clear and up to date. The next time i go back to Chicago i hope it is available i would stay here again it is a 10 out of 10.

Pet-friendly condo rentals

Guest favourite
Condo in Bridgeport
4.95 out of 5 average rating, 133 reviews

Entire 3Bed/2Bath Condo Near McCormick & Metro

MelanieRating, 5 stars2 weeks ago
Great access to Palmisano Park, and so close to Chinatown and so many other great restaurants! Private parking spot is huge in the city. Would stay again!
Top Guest favourite
Condo in Lake View
4.99 out of 5 average rating, 180 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

StevenRating, 5 stars4 days ago
Will’s flat was exactly what my son and I needed on our trip to Chicago. It completely met our expectations and felt like home. My son was impressed with the comfort of the Murphy bed. The master bedroom was palatial and well-appointed. The kitchen had everything we needed, though we only used it for breakfast each day. As we were there primarily to take in a couple of baseball games we couldn’t have been happier with the location- Wrigley Field was only a few minutes away and we were close to the red line which took us to where the White Sox play. Will was very helpful with instructions and quick to respond to our questions. Absolutely would recommend this place without hesitation.
Guest favourite
Condo in Lincoln Park
4.94 out of 5 average rating, 103 reviews

NEW luxury Old Town 1-Bedroom condo

AmyRating, 5 stars3 days ago
We would stay here again in a heartbeat. Excellent location, very walkable, unit was bright and clean, quiet. Katherine and Dimi were very responsive … even had an iron delivered as the previous iron had gone missing. Truly can’t say enough about our stay! Thank you!
Guest favourite
Condo in Pilsen Historic District
4.94 out of 5 average rating, 127 reviews

The Urban Oasis | Outdoor Lounge • Sleeps 10+

BridgetteRating, 5 stars2 days ago
The unit was as described, clean, affordable, easy to get to and home base from, and the neighborhood felt safe. There’s a coffee shop right on the corner we walked to in the mornings. We had a big group for a bachelorette and there was plenty of spaces to sleep downstairs (3 bedrooms with beds and one shared space with four beds), get ready (2 full bathrooms including two baths for kiddos), and lounge all together (large couch, big kitchen table, island seating, and outdoor covered area). Big thing for me is ceiling fans the bedrooms so that was super satisfying. Highly recommend this unit and we’d go back!
Top Guest favourite
Condo in Lake View
4.98 out of 5 average rating, 119 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

RebeccaRating, 5 stars3 weeks ago
One of my favorite Aibnbs of all time. The location is FUN - right in the center of the action in Northalsted. The space itself is beautiful and clean. The bedrooms are spacious, and the kitchen is well equipped. Allan was awesome and left us a bottle of prosecco to welcome us. Best part of the house is the huge covered front balcony - a front row seat to the joyous crowds, especially on the weekend. We saw a concert, walked to a Cubs game, spoiled the kids on Michigan Ave - and everyone agreed the balcony was our fave part of the trip. The rear deck is icing on the cake. We were in town so our kids could go to a concert and they also loved the area. If you're sensitive to noise, bring earplugs - all the action brings a bit of music - but really it's a steady din so super easy to tune out at bedtime. We love this place and can't wait to come back!
Top Guest favourite
Condo in Logan Square
4.92 out of 5 average rating, 348 reviews

Susie's Space. 2BR easy parking & pet friendly

RachelRating, 5 stars4 days ago
Susan’s home was comfortable, clean, well-equipped, and aesthetically pleasing. The bed I slept in was one of the most comfortable of my entire life—I prefer a soft mattress. As far as location goes, the street was quiet, good for walking our dog, and close enough to public transport. Plenty of buses were available. We used street parking for our car and never had problems with finding a close spot to the house whenever we did take the car out. We enjoyed the stay greatly and will stay again. Thank you, Susan!
Superhost
Condo in East Rogers Park
4.82 out of 5 average rating, 141 reviews

Marvelous Condo w/ Pri Prkng Cls to Transit &Beach

BilalRating, 5 stars2 weeks ago
Great place to live..!! Thanks kyriako.
Guest favourite
Condo in West Loop
4.96 out of 5 average rating, 231 reviews

Updated Designer Duplex In Fulton Market W/parking

NicoleRating, 5 stars4 weeks ago
Supurb stay in Fulton Market! Seth was an outstanding host—responsive, welcoming, and accomidating. The apartment was spotless, well decorated, and thoughtfully stocked with everything we needed for a comfortable stay. The beds and linens were especially cozy, making it easy to relax and feel at home. The location is superb—just steps away from a variety of highly rated restaurants. The location is superb—just steps away from a variety of highly rated restaurants. We also felt completely safe throughout our stay. The neighborhood has a welcoming, upscale vibe, which added to our peace of mind. A quick heads-up: the unit is a second-floor walk-up accessed via a private entry. Inside, as you can see has the spiral staircase; a unique architectural feature, but if you’re traveling with heavy luggage, it’s something to keep in mind. Pack accordingly! 😉 Overall, we had a wonderful experience and would gladly stay here again and agai

Condo rentals with a pool

Guest favourite
Condo in Downers Grove
4.92 out of 5 average rating, 63 reviews

Upscale, Washer Dryer, Smoke Free, Pet Free,

ChidoRating, 5 stars3 months ago
I really loved the place—it was cozy, soundproof, and felt just like home. It had a warm, inviting atmosphere and a great sense of comfort. Plus, the neighborhood felt very safe, which made our stay even better.
Guest favourite
Condo in Evanston
4.96 out of 5 average rating, 98 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

PhillipRating, 5 stars1 month ago
Great Stay - Nice unit and facility. Michelle was very responsive and helpful during my stay. Would stay in one of her properties again when I’m back in town.
Condo in The Loop
4.42 out of 5 average rating, 12 reviews

voco: Balcony & City View

AmitRating, 5 stars2 weeks ago
gorgeous views and very nice condominium. great balcony and very safe. The elevators were super fast. Even though the actual location is different than the one mentioned in listing, it still wasn't disappointing. There is enough space for a small family or a couple.
Guest favourite
Condo in Evanston
4.95 out of 5 average rating, 108 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

StaciRating, 5 stars3 weeks ago
Always responded quickly. When we had trouble with front door lock they came out quickly and addressed the problem.
Condo in Magnificent Mile
4.33 out of 5 average rating, 9 reviews

30 E. Huron #2603 Private Residence

Diego HernanRating, 5 stars25 months ago
Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.
Guest favourite
Condo in Elk Grove Village
4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars3 months ago
I am incredibly particular with places I stay. This place was simple, very clean, had everything you would need to be comfortable. Bed was great! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️
Guest favourite
Condo in Evanston
4.91 out of 5 average rating, 126 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

FeiRating, 5 stars1 week ago
可以步行到西北大学,周边环境整洁舒适宜人。屋内设施齐全,很喜欢在厨房cooking。我们全家在这里度过了愉快的一周。下次还会入住。
Guest favourite
Condo in Evanston
4.96 out of 5 average rating, 102 reviews

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

EdRating, 5 stars3 days ago
Mihyun was super responsive and our stay went without a hitch. The amenities of the building are numerous and the place was perfect for our family of four.

Quick stats about condo rentals in Woodlawn, Chicago

  • Total rentals

    50 properties

  • Nightly prices starting at

    $50 NZD before taxes and fees

  • Total number of reviews

    2K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

Destinations to explore

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