
Condo holiday rentals in Wicker Park, Chicago
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Top-rated condo rentals in Wicker Park, Chicago
Guests agree: These condos are highly rated for location, cleanliness and more.
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Popular amenities for Wicker Park, Chicago condo rentals
Weekly condo rentals

City View 3BR Condo/Garage Parki
Great location, great home, awesome value! Would highly recommend.

Urban Oasis Getaway. 6 stops to downtown!
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!

Private rooftop | Breathtaking skyline view
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.

Sun-Soaked West Loop Penthouse - Private Rooftop
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.

Lincoln Square Gem!
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.

Luxe condo w/ HOT TUB and Amazing Roof Deck!
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.

Amazing Fun Condo, City view next to 606 Trail!
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!

Two Bedroom w Porch in Wicker Park
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

Chic and Charming Vintage Condominium in Lincoln Park
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.

RockStar Pad W3A BoysTown/Wrigley Field/Parking
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!

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

Ultra clean/cozy condo, 10 mins south of Downtown!
Great host and great stay! Beautiful home. Thank you so much!

Spacious & Stylish Home at the ♥ of Wicker Park
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.

Marvelous Condo w/ Pri Prkng Cls to Transit &Beach
Great place to live..!! Thanks kyriako.

Modern Luxury In Old Town - Sleeps 4
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!

Lincoln Park Hideaway - 5 Min Walk to the Park!
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

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

voco: Balcony & City View
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.

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

30 E. Huron #2603 Private Residence
Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.

Just remodeled apartment close to airport and mall
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! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

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

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

Pond View, Washer Dryer, Non Smoking, Pet Free
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
$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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- Rentals with a fire pit Wicker Park
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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
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Wicker Park
- Willis Tower
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center