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Condo holiday 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

ManuRating, 5 stars3 days ago
Great location. On a previous review someone had commented about the noise and proximity to railway line. We did not find this a problem and do not think this is an issue at all. Kitchen has all the modern gadgets and has all you need. One issue is the elevator does not work or is switched off. Carrying large suitcases to the third floor may be a problem for some. Overall great place.
Guest favourite
Condo in Logan Square
4.81 out of 5 average rating, 286 reviews

Renovated 3br Duplex In Logan Square W/parking

OlgaRating, 5 stars3 days ago
We enjoyed a week of comfortable stay at Matt’s place! We were a family of 5 people and had enough space for everyone! We came for my daughter’s wedding and it was great to have lots of things/amenities that helped us prepare for the wedding! Garage spot was helpful! Backyard peaceful and we spent some time relaxing on the deck! Adorable cozy duplex with everything you need for the relaxed and comfortable stay! Matt was respectful, helpful and very responsive! Area is great as well! Thank you so much!!
Top Guest favourite
Condo in Lincoln Square
4.97 out of 5 average rating, 412 reviews

Lincoln Square Gem!

EvanRating, 5 stars1 week 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 favourite
Condo in Humboldt Park
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 favourite
Condo in Wicker Park
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!!
Superhost
Condo in Ukrainian Village
4.87 out of 5 average rating, 52 reviews

Art Deco Inspired Designer 2 Bed Loft In West Town

EllenRating, 5 stars1 week ago
We booked David’s place for a last minute trip to the city. We were thrilled with how beautiful and spacious the apartment was. We felt right at home, the kitchen was well equipped and the apartment was comfortable. Parking and access to the building can’t be beat!
Guest favourite
Condo in Wicker Park
4.9 out of 5 average rating, 51 reviews

2-Story Luxury Condo in Wicker Park–10 Mins to DT

TanisRating, 5 stars2 days ago
Great location in Wicker Park, walking distance to lots of restaurants, bars, etc. Condo was spotless, open and with lots of room for the six of us. Outdoor area was great with nice amenities. From start to finish Christina was amazing, very resort any questions within minutes, could not ask for a better hostess. Would definitely rent again. Christina, thank you for everything.
Top Guest favourite
Condo in Little Village
4.88 out of 5 average rating, 389 reviews

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen

CrystalRating, 5 stars1 week ago
Beautiful place to stay in Pilsen area just what we wanted! Close to downtown and amazing places to eat all around. Easy access to a lot of things to do. Beautiful place, extremely clean! We definitely enjoyed our stay at Laura’s!

Pet-friendly condo rentals

Superhost
Condo in North Side
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 favourite
Condo in Lake View
4.99 out of 5 average rating, 178 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

RonniRating, 5 starstoday
Beautiful, clean unit and Will was extremely responsive and helpful. Super clean, and the beds and furniture were soooooo comfortable! It looks exactly as it does in the photos and there are so many items included, in case you forgot something! A foot massager?! Amazing 🤣The location is perfect with lots to do close by and no shortage of options for places to eat. I feel extremely fortunate that I came across this one and will definitely book again in the future. Just perfect.
Guest favourite
Condo in Oak Park
4.94 out of 5 average rating, 241 reviews

Picture Perfect 3Bed Steps from Train and FLW

GerryRating, 5 stars2 weeks ago
Great stay at Anne’s place. She was very communicative and went out of her way to ensure we were comfortable. We would definitely recommend to anyone coming to the Chicago area!
Guest favourite
Condo in East Rogers Park
4.93 out of 5 average rating, 240 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

JenniferRating, 5 stars1 week ago
This is a WONDERFUL one bedroom apartment that is both private and spacious! The owner/host has the space fabulously decorated with an eclectic mix of original contemporary artwork and antiques. Nothing is generic about the space and it has been outfitted for guests with loving care. The host, Kaye, clearly puts much trust in her guests with her charming decor and furnishings. The amount of space, the privacy and the home-y feel make it a place we'd love to return to.
Guest favourite
Condo in Wicker Park
4.88 out of 5 average rating, 265 reviews

Spacious & Stylish Home at the ♥ of Wicker Park

TimRating, 5 starstoday
Great place for a large group to share a space. Lovely neighborhood, nice apartment, and Joe was very responsive.
Guest favourite
Condo in Lincoln Park
4.96 out of 5 average rating, 106 reviews

Large Remodeled Home in Lincoln Park, Sleeps 12!

SamiRating, 5 stars1 week ago
This was an excellent place to host a lot of visitors to Chicago! Lots to do nearby, and excellent proximity to the Red Line North/Clybourn station. The home was large, clean, and had such a nice set of helpful earplugs and towels for each bed.
Superhost
Condo in Lincoln Park
4.79 out of 5 average rating, 224 reviews

Modern Luxury In Old Town - Sleeps 4

AlexanderRating, 5 stars4 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 Old Town Triangle
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 favourite
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.
Guest favourite
Condo in Evanston
4.95 out of 5 average rating, 107 reviews

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

RemiRating, 5 stars1 month ago
Our Stay at The Bliss of Evanston was great. The host is very responsive and was very accommodating of our requests. The location and view can not be beat.
Condo in River North
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.
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 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 favourite
Condo in Evanston
4.91 out of 5 average rating, 126 reviews

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

FeiRating, 5 stars2 days ago
You can walk to Northwestern University, and the surrounding environment is clean, comfortable, and pleasant.The house is fully equipped, and I love cooking in the kitchen.Our whole family had a wonderful week here.Would stay again.
Condo in Lombard
4.91 out of 5 average rating, 46 reviews

Pond View, Washer Dryer, Non Smoking Community

AsgharRating, 5 stars6 months ago
Place was neat and very clean, enjoyed our stay, location was great as it was near all the malls and restaurants in Lombard and Oakbrook.
Guest favourite
Condo in Evanston
4.96 out of 5 average rating, 100 reviews

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

AileenRating, 5 stars1 week 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.

Quick stats about condo rentals in Wicker Park, Chicago

  • Total rentals

    30 properties

  • Nightly prices starting at

    $83 NZD 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

  • Wi-Fi availability

    30 properties include access to Wi-Fi

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