
Holiday rentals with beach access in Woodlawn, Chicago
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Top-rated rentals with beach access in Woodlawn, Chicago
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Popular amenities for rentals with beach access in Woodlawn, Chicago
Apartment rentals with beach access

3bdrm/2bthrm in restored brownstone in Bronzeville
Phil was very responsive and accommodating. Place was in a great location and clean. I would recommend anyone to stay at this location.

51st Floor MagMile Penthouse Views Balcony Pool
Highly recommend. Very nice, clean place with amazing views in a great location! Much to do within walking distance and very close to the Grand & State redline and bus lines which makes it easy to get around using public transit.

Andersonville's Secret Garden: 2 beds, 1 bath
Such a stylish and cozy spot in the heart of Andersonville! The beds were incredibly comfortable and the space had so much charm. Just steps away from great shops, restaurants, and everything else you would need near Clark street. Would definitely stay again!

Spacious 3 bdrm apt. near NU + Chicago + lake.
Our family of five felt right at home and thoroughly enjoyed our 3-night stay. Daniela's place is comfortable and charming. Its location in a peaceful neighborhood was a restful reprieve after full days sightseeing in Chicago. The close proximity to the lake and downtown Evanston restaurants/shops was another plus -- as was the dedicated parking spot. On top of all that, Daniela is a thoughtful host who was helpful, understanding and responsive throughout our stay. We look forward to coming back and highly recommend this beautiful condo.

Andersonville Garden Living
I love the Andersonville neighborhood and the stay went great! We got in way later than expected but we still were able to find parking about 2 blocks away (5 min walk). The next day parking was a breeze. The area is so nice, right off Clark and close to lots of great food/coffee/drinks. Thank you Joseph!

Andersonville Bicycle Studio
My wife, son and daughter stayed at Tim's place when son ran the Chicago half-marathon. Tim was one of the best AirBNB hosts ever. He left my family a personal welcome note and let them in early from their morning flight. The space was immaculate, very charming, and super comfortable. Chicago neighborhoods can be dicey. This felt totally safe day and night. I was unable to come last minute due to work. My wife wants us to return together for a romantic weekend. A great experience in every way. Thank you!

Quiet city getaway by beach in fun neighborhood
A spacious and comfortable unit in a residential neighborhood close to popular businesses and entertainment in the Andersonville neighborhood of Chicago. Super convenient to get everywhere I was heading to. Hosts have thought of everything you might need, including ear plugs for sleep, and bicycles with locks and helmets available to borrow. Hosts were helpful and responsive and the welcome binder had great information without having too much. I had a perfect stay and would stay again.

Beautiful Hollywood-Ridge Suite in Edgewater
Dorothy was very helpful and accommodating. She was communicating with us about construction around her place and challenges we might face getting there. Our travel plans changed several times and she was flexible and remained helpful through all of the changes. Another positive for Dorothy was the extras at the place. Bagels, yogurt, coffee, and toiletries were all available for us. Loved the peaceful location close to amenities. A good hub to explore Chicago from. Thank you!
House rentals with beach access

Gold Coast Home|Rooftop |PoolTable |Parking |Beach
Rasheed was very attentive. His home is in an excellent location, walking distance to resturants and shopping. The rooftop provided a spectular view of the city. I would definitely recommend Rasheed's home on a trip to Chicago!

Amazing historic campus mansion!
Caryl was extremely helpful with a check in process and she introduced us the property as well as surrounding local attractions. We felt the place was warm and very spacious for our group and we had a pleasant stay.

House 5BED/3BATH/1PARKING close to Downtown & Lake
We would definitely use this location again when in town with family. Specious and only a short uber ride from everything we needed.

CasaNova Modern City Living
Beautiful home layout and very spacious! Location was a quick drive to the city, which was convenient. Host was also very kind and attentive. Thank you Ms. Lilly for our stay!

Historic Old Town, Fabulous 4 Bedroom Home
We had a party of 6 and there was plenty of room to spread out. Each couple had their own bathroom. Families with kids can have their kids nearby at night which can be helpful with younger children. We had a large vehicle which didn’t fit through the gate but we were able to get permits for street parking each night which was readily available.

Exec Lux home wth 3 Level,6 Bdrms/3bth & 2 Kitchen
The neighborhood was quiet and the space was clean and as advertised. My only complaint was there were no paper towels in the home lol After ripping and running all over the city before getting to there I was very frustrated about that. But I would definitely stay again.

Ideal Group Getaway: Best Location, Parking, Patio
Great place. Great location. No issues at all. I would rent again. It's a good spot between the Gold Coast and Lincoln park and beer some really good restaurants. Place was as described and would have no issues staying there again.

Private Downtown Retreat with Rooftop Oasis
Our daughter was graduating from University of Chicago while our other daughter graduated from USAF flight school in Mississippi, and our family and friends visited from locations scattered around multiple time zones. Florin's location was simply the perfect place to handle such incoming chaos while lowering blood pressure to encourage a wonderful graduation experience headache-free. The rooftop experience was stunning, and everybody has been raving about the furnishings and easy-going environment in such a lovely place. The bathrooms and bedrooms were spa-worthy, and there were simply so many careful and thoughtful touches at this location that made it hard to leave! Florin has multiple parking options, but we only needed one nearby, offstreet parking place that was never a problem---surprising for a big city like Chicago! In short, this was probably the finest AirBnB we ever visited, and we are so grateful for such an exclamation point on a magical weekend. Thank you, Florin!
Apartment rentals with beach access

RockStar Pad W3A BoysTown/Wrigley Field/Parking
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.

The Ramblers Inn, Northside NEW Reno w/parking!
The condo is in a quiet and attractive neighborhood and the hosts answered my few questions promptly. The place was very clean and although the bedrooms were small, it was nice that each of us (nana and two teens) could have their own space.

Cozy 3BR on Chicago's North Side & Free Parking
This home was beautifully decorated, the beds were super comfortable, from the mattresses to the linens. We loved how clean and clearly cared for everything was, and Mark and Marcelo were responsive and helpful anytime we had a question. We needed a place that felt like home while visiting Chicago for my son's graduation, and this was perfect for the three of us. An added bonus was that there is a designated parking spot on the premises.

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)
WWWWOOOWWW!! This host team was EXCEPTIONAL! I’ve stayed in plenty of AirBnBs, and I’ve NEVER encountered a host that was so EXTREMELY accommodating, responsive, and kind! Other hosts should take a page out of their book! The only thing I would change, and it’s not a bad thing (just a matter of preference); I would have some type of blinds or drapes over the living room windows. This will allow for privacy when you’re sitting in the living/dining room areas at night with the lights on inside. Hands down, we would without a doubt book with this team again! Thank you Wendy, Matt, and your co-hosts for helping to make our time in Chicago wonderful!

Pets OK | Walk Score 95 | Desk | 1,750ft² |W/D
Great location, beautiful neighborhood — such a lovely place to stay! Enjoyed a girls weekend here, comfortably fitting 5 of us. Danny was very kind and responsive with any questions we had.

FreeParking/Laundry/BigSpace!/FamilyFun!/GameRoom!
I recently had the pleasure of staying at this property, and I can confidently say it was a fantastic experience. The accommodations were exactly as described, making it easy to settle in and feel at home right away. I highly recommend to anyone looking for a comfortable and welcoming place to stay!

Andersonville: 3-bed, 2-bath w/ Dining RM & EZ PKG
Nice place in a great neighborhood. Really appreciated the opportunity to leave the car parked and walk and train everywhere. The house was clean and tidy and Ari provided a list of neighborhood dining recommendations. We had six people in our party and there was just enough space that we didn't end up sick of each other. Overall, the trip was wonderful.

Large 2BR, 2BA, patio, sunroom, W/D, L-kitchen
Pablo was an incredibly responsive and helpful host, even volunteering to have us check in early. His place was spacious (can accommodate 4-5 people) and comfortable. . . really a home away from home. Had everything we needed for a 5-day stay . . washer/dryer a plus! Parking can be a challenge, but using SPOT Hero helped us identify available spots. While next to the train, the train noise was more like white noise and did not disturb us. Would definitely stay again!
Quick stats about holiday rentals with beach access in Woodlawn, Chicago
Total rentals
20 properties
Nightly prices starting at
$39 SGD before taxes and fees
Total number of reviews
950 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Moraine Hills State Park