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Apartment holiday rentals in Wicker Park, Chicago

Find and book unique apartments on Airbnb

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Popular amenities for Wicker Park, Chicago apartment rentals

Weekly apartment rentals

Guest favourite
Flat in West Lake View
4.95 out of 5 average rating, 121 reviews

Chic retreat near the best of Lakeview & Wrigley

KariRating, 5 stars1 week ago
Really comfortable and nicely appointed apartment. Great location, neighborhood, and hosts. I look forward to staying in this Airbnb again when visiting family.
Guest favourite
Flat in Wicker Park
4.95 out of 5 average rating, 119 reviews

Bright two bedroom garden apartment

ShannonRating, 5 stars3 days ago
Loved this stay! My friend and I felt right at home. Such a safe neighborhood that’s not far from local shops and restaurants. 5 star stay!!
Superhost
Flat in West Town
4.87 out of 5 average rating, 230 reviews

Cozy Ukrainian Village Two Bedroom Apartment

HaetsalRating, 5 stars3 months ago
Very good accommodation! I was really comfortable for about a week. It was spacious, comfortable I‘ll use it again next time Thank you for providing a good accommodation
Guest favourite
Flat in Wicker Park
4.91 out of 5 average rating, 53 reviews

Pierce Place in Wicker

JaneRating, 5 stars1 week ago
Perfect stay in Wicker Park! This is a great, quiet location walkable to many shops and restaurants. Street parking was not hard to find. The unit is very well appointed with everything needed in addition to some thoughtful touches for our convenience. We would absolutely stay again and highly recommend it. We are thankful to Jacqueline for offering this space.
Top guest favourite
Flat in Logan Square
5 out of 5 average rating, 58 reviews

The Heart of Bucktown

EstherRating, 5 stars1 day ago
I had a wonderful experience at Charles' place. I would like to thank Charles again for installing the AC unit during the heatwave. I loved the neighborhood; it felt safe and private, and there were endless options for coffee and food. Additionally, public transportation was easily accessible and conveniently located nearby. Thank you!
Superhost
Flat in Wicker Park
4.96 out of 5 average rating, 142 reviews

Hip 3 BR in Heart of Historic Wicker Park!

BenjaminRating, 5 stars3 weeks ago
Beautiful apartment, amazing location, great hosts. Never had trouble finding nearby parking, often within sight of the apartment (though be sure to avoid permit streets). Great coffee across the street. A+ bakery two blocks away (Lost Larsen). Wine bar around the corner. Great food everywhere. And that’s just within two blocks. Walk a few more and you get all of Wicker Park. Transit was easy too (bus and el).
Superhost
Flat in Lincoln Square
4.76 out of 5 average rating, 223 reviews

Tidy Designer Flat in Heart of Lincoln Square

AndreaRating, 5 stars3 weeks ago
What a find! Quiet, clean, well located and easy to communicate with. Had a great weekend in Chicago!
Guest favourite
Flat in Logan Square
4.88 out of 5 average rating, 102 reviews

Bright & Cozy 1-Bedroom Apartment in Logan Square

SarahRating, 5 stars1 week ago
Very clean and peaceful place to stay. Loved the space and location!!

Private apartment rentals

Top guest favourite
Flat in Wicker Park
4.96 out of 5 average rating, 159 reviews

Hip Chicago Condo in fun shopping and dining area

DionneRating, 5 stars2 weeks ago
Emily’s place is peaceful and homey, yet right in the heart of a vibrant neighborhood. Wicker Park was a nice walk from her home as well. TONS of restaurants and shopping literally a couple of blocks from her house. The train stop is a 5 minute walk away and downtown is less than a 15 minute uber ride. Emily is a very considerate and communicative host and I would stay here again. Thank you for sharing your home with me!
Top guest favourite
Flat in Chicago
4.99 out of 5 average rating, 233 reviews

Modern Apt with style & comfort in Pilsen Chicago

AnthonyRating, 5 stars1 week ago
A-MAZ-ING stay! My wife and I had such a blast in Chicago. GOGO was very kind and inviting, good energy! The place was exactly what we wanted with all the amenities. Sparking water in the fridge which was a treat after waking 18k everyday. As a runner, there was plenty of sidewalk and things to see. I recommend running up LEAVITT to 18th street and take 18th down for a nice 3 to 5 mile run. The L train “pink line “ was close and walking back at night we felt relatively safe. I would high recommend staying here in Pilsen area the next time you are in Chicago. Mahalo
Top guest favourite
Flat in Wicker Park
5 out of 5 average rating, 58 reviews

The Bell House: Apartment #1

GinaRating, 5 stars1 week ago
Another great stay at Christina’s location lovely home! We had no problem finding street parking on their quiet street. We got to enjoy sitting out on the back deck- the patio and garden is lovely! The beds are comfortable and the home has everything you need!
Superhost
Flat in Wicker Park
4.82 out of 5 average rating, 217 reviews

Ina's Beachwood Inn In the Heart of Wicker Park

MarioRating, 5 stars5 days ago
A great place to stay. Would absolutely book again
Top guest favourite
Flat in Ukrainian Village
4.93 out of 5 average rating, 224 reviews

Spacious & Clean Ukrainian Village 2 Bedroom!

CherylRating, 5 stars1 week ago
From the first communication, Catherine was incredibly responsive. Her instructions and expectations were clear, concise and accurate. The space was immaculately clean. Kitchen was well-appointed. We only used one bed, which was extremely comfortable-I imagine the other one is as well. If we return in the future, I hope to bring our daughter and her husband as well, as the space would comfortably accommodate two couples. Generous seating in the living area, and a dining table for 4. There were plenty of towels and toilet paper. There is a wonderful collection of a great variety of books and games. The neighborhood is beautiful and feels very family-friendly and safe. For us, it worked out perfectly, as it was easy walking distance to our son and daughter-in-law, who we were visiting. There is so much to do and see within walking distance - great restaurants and coffeeshops. I strongly recommend this rental to others, and hope to return on our next visit to Chicago.
Top guest favourite
Flat in Magnificent Mile
4.98 out of 5 average rating, 160 reviews

Elegant Suite in Gold Coast

MikeRating, 5 stars4 days ago
A perfect stay! Next time I am in Chicago, this will be my first choice. I "second" all the great things that everyone else has said. I was here for a multi-day conference at a very nearby hotel, and I am so glad I chose here over the host hotel. Wonderful staff, great communication! Top notch in every respect! Thank you!
Guest favourite
Flat in West Town
4.97 out of 5 average rating, 100 reviews

Sunny Wicker Park Apartment - 2BR with Deck

ThomRating, 5 stars2 weeks ago
Very lovely quiet spot to stay in Chicago. The place was spotless and very comfortable. I will be booking again in the future.
Guest favourite
Flat in West Town
4.97 out of 5 average rating, 211 reviews

The Noble Farmhouse, w/ Garden in West Town

MaryRating, 5 stars6 days ago
We loved The Noble Farmhouse! The neighborhood was so cute with tons of great restaurants and things to do. Our favorite part might have been the private garden space, though 🌿

Apartment rentals with a hot tub

Superhost
Flat in West Rogers Park
4.85 out of 5 average rating, 80 reviews

Spacious Beautiful Condo

SophiaRating, 5 stars1 week ago
We came for our daughter’s graduation and stayed a few extra days to tour the city. This place was perfectly located for both occasions. It was much more spacious than we expected, and everything was very clean. We especially appreciated the fresh towels and beddings. Our only wish is that the beds were a bit larger, especially the double bed, which would be more comfortable for a couple if it were at least a queen size. That said, the beds were very comfortable. Overall, we had a wonderful stay - definitely one of our best Airbnb experiences!
Superhost
Flat in Chicago
4.88 out of 5 average rating, 16 reviews

Large Studio Apartment with no cleaning fee

Latrice Rating, 5 stars1 week ago
David and his co-host were excellent. Our family enjoyed our stay. We used to live in the Bronzeville area and love the new additions to the neighborhood. Everything met or exceeded our expectations.
Superhost
Flat in West Loop
4.96 out of 5 average rating, 27 reviews

Skyline Oasis: City & Lake Views

NatalieRating, 5 stars3 weeks ago
Perfect weeklong stay in Chicago! The apartment is well equipped and makes you feel right at home. The building is connected via sky bridge to Jewel making it easy to grab groceries. The location cannot be beat - easy access to West Loop, Wicker Park, River North. The hosts were fantastic and flexible with our check in times. Looking forward to coming back!
Superhost
Flat in West Town
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars1 month ago
We stayed with my family for 3 days n loved the place it's ambience, cleanliness, very well equipped with all the necessities.....this place definitely feels like home and the hosts are very kind and quick with there response. Wherever in future I am coming to chicago shall book this place.
Superhost
Flat in West Loop
4.83 out of 5 average rating, 120 reviews

Penthouse Near Fulton: Skyline, Spacious

EmadRating, 5 stars4 days ago
Great place nice views , communication with host very smooth !
Superhost
Flat in The Loop
4.69 out of 5 average rating, 49 reviews

Sentral 1 Bedroom Apt in South Loop Chicago

RichardRating, 5 stars2 weeks ago
Sentral worked great for us going to a graduation for a long weekend. Unit is exactly as described, modern, and clean. Kitchen utensils are reasonable while shelves and refrig are empty save for some coffee so if going to cook/eat be sure to bring everything such as butter, spices, etc. - a Trader Joes is 3 blocks away. Price is not cheap but is very convenient and easy so on balance okay for us. Front desk is very helpful and cheerful.
Superhost
Flat in Belmont Cragin
4.98 out of 5 average rating, 119 reviews

Belmont Pleasures - hot tub / arcade gaming room

AustinRating, 5 stars1 week ago
Stay was great and Mariam was a super host. The space was exactly as pictured and all the games were a blast. Miriam even checked in a couple times to make sure we had everything we need and that we were having a good time. For sure would stay here again.
Superhost
Flat in The Loop
4.9 out of 5 average rating, 30 reviews

City Skyline Suite (2BD / 2BA)

NataliaRating, 5 stars1 week ago
We loved this apartment and our trip to Chicago. We felt safe when coming home late at night and we walked everywhere, even though train stations are pretty close. The views from 17th floor are spectacular in 3 directions, including Lake Michigan and Willis Tower. The place is very clean and comfortable. I wish we could stay longer.

Quick stats about flat rentals in Wicker Park, Chicago

  • Total rentals

    90 properties

  • Nightly prices starting at

    $51 SGD before taxes and fees

  • Total number of reviews

    6.1K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

Destinations to explore

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