Condo vacation rentals in Woodlawn, Chicago

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Top-rated condo rentals in Woodlawn, Chicago

Guests agree: these condos are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Avondale

4.95 out of 5 average rating, 102 reviews

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE!! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops. Free parking on Lawndale Ave.

Guest favorite

Condo in Bridgeport

4.89 out of 5 average rating, 111 reviews

Convenient & Spacious 3BR Condo w/Free Parking

Get cozy in this spacious 3-bedroom condo, conveniently located 3 blocks from the Halsted Orange Line overlooking Palmisano Park and only 5 minutes' drive to McCormick Place. Clean, neat, modern and comfortable, the condo offers spacious living space with an open kitchen, washer/dryer, and an outdoor balcony perfect for families and groups. Hungry? Our complex offers a few delicious high rated yelp restaurant options to fulfill your appetite. We look forward to hosting you and your guests!

Superhost

Condo in Lincoln Park

4.8 out of 5 average rating, 160 reviews

Massive Old Town Home Steps to Wells St & Beach

Start your Windy City adventures in my spacious 3rd-floor duplex in the heart of Chicago's vibrant Old Town neighborhood! This 8 bed, 4 bath home comfortably sleeps up to 20 guests, making it perfect for large groups or families. Enjoy modern furnishings, a fully equipped kitchen and two cozy living areas to relax in after exploring the city. Steps from popular restaurants, bars, boutiques and the lake, you’ll be immersed in local charm. (Please note, parties and large events are not allowed)

Superhost

Condo in Uptown

4.91 out of 5 average rating, 152 reviews

Stunning, Spacious, & Sunny 2bed Uptown Condo

Welcome to your home away from home in Uptown! My bright and inviting condo offers a perfect blend of comfort and convenience, with your own sunny living room to relax, fully-equipped kitchen and separate dining room, spacious private bedroom, serene sunroom with full bed for extra guests, and a workspace for business travelers. Just steps from the lakefront and Montrose Beach, and a 6-minute walk to the Wilson Red Line, this location is excellent for exploring all that Chicago has to offer.

Guest favorite

Condo in Lincoln Park

4.91 out of 5 average rating, 100 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

This bright and airy 2 bedroom/2 bath condo has been completely renovated with a designer’s eye and creative touch. The condo comes with 2 parking spaces in the adjacent private gated parking lot. The covered patio space on the back deck offers spectacular views of the Chicago skyline – enjoy your morning coffee or evening cocktail overlooking the city. L Train Stops & tons of restaurants, bars and entertainment within walking distance. Please contact me for discounts on monthly stays!

Guest favorite

Condo in West Town

4.92 out of 5 average rating, 113 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

Experience a calm and soothing stay in a space bathed with light and nestled amongst the trees. This top floor unit in a 3-flat condominium building offers you the serenity of a neighborhood with tree lined streets, and the convenience of being 3 miles from the heart of downtown Chicago. As a bonus, you're a 2min walk from public transportation. For something closer to home, Wicker Park and Humboldt Park offer great dining and culture steps away. We look forward to hosting you!

Guest favorite

Condo in River North

4.98 out of 5 average rating, 132 reviews

Luxurious River North 3BR/2BA- Free Onsite Parking

Experience an urban oasis unlike any other: - Complimentary parking for one vehicle in our attached lot - Spacious, recently renovated kitchen - Immersive entertainment with large-screen TVs - Unwind with a game of poker or foosball at our dedicated tables - Conveniently located within walking distance of the Magnificent Mile - Surrounded by an array of vibrant bars, restaurants, and nightlife - Embrace our inviting patio Indulge in a memorable stay at our 3rd-floor condo!

Guest favorite

Condo in River North

4.91 out of 5 average rating, 148 reviews

Brilliant Downtown Chicago 3-Bedroom Condominium

Situated in downtown Chicago, right next to the Godfrey Hotel, this spacious and bright 3-bedroom, 2-bathroom condominium is perfectly suited to deliver the best adventures the Windy City has to offer. Our vacation home includes four sleeping areas with 1 King & 3 Queen sized memory foam mattresses and features everything from a fully-stocked kitchen to smart gadgets like Alexa. PARKING: We offer a $30 per day parking credit. This credit pays for most or all parking costs.

Guest favorite

Condo in West Town

4.98 out of 5 average rating, 160 reviews

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Top guest favorite

Condo in Uptown

4.98 out of 5 average rating, 270 reviews

Near Lake Michigan & Wrigley Field

Available 2B/2B condo with 2 King Size Beds. One block from the Aragon Ballroom and Riviera with great views of Uptown and two blocks from Lake Michigan. It’s also a perfect place to stay if your in town for a Cubs game. You can see the stadium from the rooftop deck. Walking distance to everything you need, 2 train stations, groceries, gym, restaurants/ bars. The perfect place to come and go as you please with easy key code entry.

Guest favorite

Condo in Wicker Park

4.83 out of 5 average rating, 338 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of amenities. Just a block from everything this neighborhood has to offer and 2 blocks from the 'L' to take you downtown or to O'hare Airport. Premium location to effortlessly walk from our quiet side street and be in the heart of all the entertainment! I provide all the essentials to make your stay easy and comfortable!

Top guest favorite

Condo in Edgewater

4.97 out of 5 average rating, 111 reviews

Steps from the Lake, Lovely 3-Bedroom Condo

Enjoy all that Chicago has to offer in this beautiful Edgewater home. Lakefront beaches are steps away, as is the red-line Granville stop. This condo is walking distance to the Loyola campus, many restaurants, grocery stores, gyms, antique stores, and more! There is ample street parking on Lakewood, often there is a space right outside the house. We provide daily parking passes for you to use during your stay.

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What guests are saying

Chic and Charming Vintage Condominium in Lincoln Park

4.84 out of 5 average rating, 354 reviews2 weeks ago

Colin's place is cute, clean, and VERY convenient! Just a short walk to the Fullerton or Armitage L stations. Tons of closeby restaurants, and a very good coffee shop/diner just downstairs below us! It is on a busy corner, so be warned the traffic & evening pedestrian noise can be loud, especially in the corner turret bedroom, but the heater makes pretty good white noise. Thanks for a perfect homebase for our girl weekend away!

Condo in Lincoln Park

What guests are saying

A Stones Throw from U Chicago South Campus!

4.87 out of 5 average rating, 234 reviews1 week ago

Great location within walking distance of University of Chicago and in a safe neighbourhood. Basement apartment with 2 bedrooms. Bed was comfortable & extra pillows & blankets were provided. Toilet & kitchen facilities were slightly dated but functional. Appreciated the use of washer/dryer & complimentary coffee/tea. Very hospitable host!

Condo in Woodlawn

What guests are saying

Foosball, Steps from Wrigley, Private Parking

4.92 out of 5 average rating, 113 reviews2 weeks ago

Very easy walk to Wrigley field, many restaurants. Chose this place because of the proximity to Red Line and Wrigley. Perfect for 2 couples! very clean, and well-equipped, as pictured. as described. The fireplace, fresh tulips and coffee were very welcoming. Karolina was a wonderful host.

Condo in Wrigleyville

What guests are saying

RockStar Pad W3A BoysTown/Wrigley Field/Parking

4.99 out of 5 average rating, 161 reviews1 week ago

Will's place is exactly as described. We were in town to visit colleges for our daughter. The location is close to public transportation which allowed us to visit both schools without a car. The unit itself is in a nice part of Chicago. There are several restaurants in walking distance. We absolutely loved the decor and added touches of the unit Will was also very responsive and accommodating.

Condo in Lake View

What guests are saying

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

4.98 out of 5 average rating, 115 reviews2 weeks ago

This is my favorite place to stay in all of Chicago! I try to come up 1-2 times a year and checking to make sure this spot is available is the first thing I do when planning out my trip(s). The apartment is spacious, comfortable, and clean; central to a lot of fun neighborhoods, and right above (and across) from some of the best nightlife in the city. Allan is an awesome host, always available if something’s needed, and super communicative. I’m already looking forward to my next visit so I can stay here again!

Condo in Lake View

What guests are saying

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)

4.88 out of 5 average rating, 192 reviews1 month ago

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!

Condo in Gold Coast

What guests are saying

Modern Luxury In Old Town - Sleeps 4

4.78 out of 5 average rating, 219 reviews2 weeks ago

What a perfect location and neighborhood! We were able to walk to the Lincoln Park Zoo, to Second City, and various wonderful bakeries and restaurants! We always felt safe, no matter the time of day or night. Robert was a very responsive host, but, honestly, we didn't need him for much.... his home was clean, pretty well-stocked, and the beds were very comfortable. I would definitely recommend this place!

Condo in Lincoln Park