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Condo vacation rentals in Wicker Park, Chicago

Find and book unique condos on Airbnb

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Popular amenities for Wicker Park, Chicago condo rentals

Weekly condo rentals

Superhost
Condo in Wicker Park
4.87 out of 5 average rating, 38 reviews

City View 3BR Condo/Garage Parki

BradleyRating, 5 stars4 weeks ago
Great location, great home, awesome value! Would highly recommend.
Guest favorite
Condo in Humboldt Park
4.93 out of 5 average rating, 68 reviews

Urban Oasis Getaway. 6 stops to downtown!

LydiaRating, 5 stars1 week ago
The hosts are great—very responsive and accommodating. It’s a lovely space, with a fully functioning kitchen and very walkable to a close cta stop that’s a quick 30 minutes downtown. Area around the place is lower income, so if you’re not used to being in a city, you maybe feel less comfortable. Would recommend if you’re comfortable with urban environments though!
Top guest favorite
Condo in West Loop
5 out of 5 average rating, 30 reviews

Private rooftop | Breathtaking skyline view

BrianRating, 5 stars1 week ago
The space was exactly as advertised, roof top patio was awesome. Location was great and Anna was easy to work with. Definitely recommend, we would stay here again.
Top guest favorite
Condo in West Loop
5 out of 5 average rating, 57 reviews

Sun-Soaked West Loop Penthouse - Private Rooftop

KendallRating, 5 stars2 weeks ago
We stayed at Reggie’s place for Memorial Day weekend as a family of 5 (2 Adults, a 4 year old, twin 2 year olds). Reggie was very easy to communicate with from the first booking request. He let us know that there couldn’t be loud noise after 10 am (no issue for us) before confirming the booking. We had no issues with check in or check out, and he was responsive to every question. The location was perfect and walkable to so many things, including all the restaurants in west loop and worked well for our family and dog.
Top guest favorite
Condo in Lincoln Square
4.97 out of 5 average rating, 412 reviews

Lincoln Square Gem!

EvanRating, 5 stars6 days ago
Great location, and easy access to all main streets. The neighborhood is quiet, and very safe. The people in the neighborhood were very welcoming. The condo was nice, very spacious and a great value for the cost.
Guest favorite
Condo in Wicker Park
4.92 out of 5 average rating, 38 reviews

Luxe condo w/ HOT TUB and Amazing Roof Deck!

RickyRating, 5 stars2 months ago
From check-in to check-out, the stay was great! The place looked exactly like the photos and was in a great neighborhood. Shops, restaurants and bars all within 5-10 min walk. We even enjoyed the hot tub one late afternoon while enjoying the skyline and sunset in the back of us. Will definitely look to book this rental in our future Chicago trips.
Guest favorite
Condo in Logan Square
4.93 out of 5 average rating, 61 reviews

Amazing Fun Condo, City view next to 606 Trail!

StephRating, 5 stars1 week ago
Ken’s place was a great stay! Such a unique home with so much to see inside—decor, art, photos, and trinkets. We enjoyed relaxing in the space between exploring the city. Would recommend to anyone who is considering staying in Chicago!
Guest favorite
Condo in West Town
4.94 out of 5 average rating, 63 reviews

Two Bedroom w Porch in Wicker Park

StephanieRating, 5 stars2 weeks ago
This was our first time traveling with our dog and we were a bit nervous. Stephen was great and dog-sit to make sure our dog didn’t bark too much. The location of the apt was great..4 minute walk to Starbucks, restaurants. Neighborhood felt safe and was quiet, even for a city. Apt was clean, beds were comfy and outside porch was an added bonus. I would 100% recommend this place!!

Pet-friendly condo rentals

Guest favorite
Condo in Lincoln Park
4.83 out of 5 average rating, 362 reviews

Chic and Charming Vintage Condominium in Lincoln Park

PatrickRating, 5 stars2 weeks ago
We had a terrific stay and would definitely recommend it to others. Great location, especially if you are doing anything around Lincoln Park, DePaul, etc. The dedicated parking space was really helpful (there are 2 of them, but we only had one car). We had six people and were very comfortable. Colin is very responsive as well.
Top guest favorite
Condo in Lake View
4.99 out of 5 average rating, 177 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

BenjaminRating, 5 stars1 day ago
My dad and I were on a baseball road trip and this was a perfect place for a cubs game! About a 15 minute walk. Will was responsive and friendly, and the place might have been one of the coolest bnbs. Such a fun and relaxing spot. Would easily stay again!
Superhost
Condo in Chicago
4.87 out of 5 average rating, 119 reviews

Unique 2BR/2BA FREE Street Parking/WI-FI Near DT

AlfredoRating, 5 stars2 weeks ago
Everything went well. Place was very nice and the host was very responsive when I needed help and accommodative as well. Highly recommend if needed a place near downtown.
Guest favorite
Condo in Chicago
4.91 out of 5 average rating, 163 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

AngeliqueRating, 5 stars2 weeks ago
Great host and great stay! Beautiful home. Thank you so much!
Guest favorite
Condo in Wicker Park
4.88 out of 5 average rating, 264 reviews

Spacious & Stylish Home at the ♥ of Wicker Park

OscarRating, 5 stars3 weeks ago
It's was a lovely spacious home with great amenties and a fully stocked kitchen. The location was peaceful and quiet and had good restaurants and coffee shops at walking distance.
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 stars1 week ago
Great place to live..!! Thanks kyriako.
Superhost
Condo in Lincoln Park
4.79 out of 5 average rating, 224 reviews

Modern Luxury In Old Town - Sleeps 4

AlexanderRating, 5 stars3 weeks ago
I had a great stay! The Airbnb was easy to get to and in a fantastic location within walking distance to restaurants, bars, gyms, and public transportation. The space was very clean and well-maintained. Would definitely recommend and stay here again!
Superhost
Condo in Lincoln Park
4.88 out of 5 average rating, 154 reviews

Lincoln Park Hideaway - 5 Min Walk to the Park!

SydneyRating, 5 stars2 weeks ago
Cindy was a lovely and responsive host and the apartment was great. She was very responsive and let me adjust the booking without any hassle. There was plenty of towels and blankets, and the coffee area was well stocked. Location was in a great area of lincoln park very close to the zoo & actual park area and not a far walk to the cta/many bus stops. Would definitely recommend!

Condo rentals with a pool

Guest favorite
Condo in Evanston
4.96 out of 5 average rating, 97 reviews

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

AaronRating, 5 stars1 month ago
I would highly recommend Michelle's listing! The listing is spacious and perfect for a couple or small family (we had our <1 year old). Michelle is communicative, all the instructions are clear, and the location is convenient.
Condo in The Loop
4.4 out of 5 average rating, 10 reviews

voco: Balcony & City View

BrookeRating, 5 stars3 weeks ago
Our stay here worked out perfectly. The host was nice, and the location was centrally located to great shopping and restaurants. Very private and safe. The view at night was beautiful.
Guest favorite
Condo in Evanston
4.95 out of 5 average rating, 106 reviews

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

JasonRating, 5 stars1 month ago
Our stay in Evanston was great! The apartment is close to all of downtown Evanston, the Metra, and the L. Also easy access to NU. Everything was just as it says and the free underground parking is a HUGE plus!
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 favorite
Condo in Elk Grove Village
4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars2 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 favorite
Condo in Evanston
4.91 out of 5 average rating, 126 reviews

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

FeiRating, 5 stars1 day ago
You can walk to Northwestern University, and the surrounding environment is clean and comfortable.The house is fully furnished, I love cooking in the kitchen.Our whole family had a great week here.Would stay again.
Guest favorite
Condo in Evanston
4.96 out of 5 average rating, 100 reviews

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

AileenRating, 5 stars6 days ago
Space was clean and in a charming, walkable city. The view in the living room was beautiful. The neighbors were quiet. The coffee in the condo and in the lounge was surprisingly delightful. Our group of friends had a great time, and this would be a perfect place for a family.
Condo in Lombard
4.93 out of 5 average rating, 46 reviews

Pond View, Washer Dryer, Non Smoking, Pet Free

Moua ShouaRating, 5 stars4 months ago
Our stay was lovely. The unit was clean, and it had everything we needed. Instructions on how to get in were clear, and if I had any questions Briana promptly responded. If/when we visit Lombard again, we'll keep this airbnb in mind.

Quick stats about condo rentals in Wicker Park, Chicago

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$10,449 GYD before taxes and fees

  • Total number of reviews

    2.6K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

Destinations to explore

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  3. Illinois
  4. Cook County
  5. Chicago
  6. Wicker Park
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