Apartment holiday rentals in Wicker Park, Chicago

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Popular amenities for Wicker Park, Chicago apartment rentals

Weekly apartment rentals

Guest favourite
Flat in West Town
4.96 out of 5 average rating, 141 reviews

Bohemian Moto Inn

ElyseRating, 5 stars1 week ago
Nicole's place was great! It is a great location. I am a bad sleeper and the bedrooms were super quiet, which I loved. Nicole provided clear instructions to check in. The only issue we had was determining which key was for what since they weren't marked, and also opening the apartment door since the floor or door needed to be sanded and would get jammed. Besides that everything was fantastic. The place has plenty of space and the balcony is a nice extra perk. I would stay here in the future. Thank you Nicole!
Top guest favourite
Flat in Wicker Park
5 out of 5 average rating, 57 reviews

The Bell House: Apartment #1

AntoinetteRating, 5 stars1 week ago
This was a great stay! We were so pleased with the place as it was exactly as stated in the listing and the pictures. It was a wonderful neighborhood. The only disappointing thing was that our stay was so short we did not get to enjoy all the things so close as it is such a walkable area - restaurants around the corner with parks and other activities close by. Christina was always quick to respond to messages and I appreciated her thoughtfulness. She had indicated before we arrived that air quality had not been the best and provided an HEPA filter which was in addition to the HVAC filter in the house. We would definitely look to stay here again whenever visiting the area!
Top guest favourite
Flat in West Town
4.99 out of 5 average rating, 85 reviews

Humboldt Park Retreat: Skylights & Queen Beds

MollyRating, 5 stars1 day ago
We were so impressed with this airbnb! It was immaculately clean and beautifully decorated. It was very peaceful and quiet to come back to after our busy days exploring the city. We especially loved the kitchen amenities like high quality olive oil and two types of filtered water! Christine thought of everything! We’d love to come back again!
Top guest favourite
Flat in Lincoln Park
5 out of 5 average rating, 264 reviews

Explore Lincoln Park from a Polished Apartment

TomRating, 5 stars1 day ago
There is no way I/we can do a review of Elizabeth's beautiful apartment in just 1,000 characters. Met Elizabeth personally, made a wonderful connection. It's the most awesome airbnb we've ever stayed at. The apartment has been beautifully remodeled. As a retired general contractor, I was very impressed. The neighborhood is fantastic; great for walking, shopping, and there are restaurants galore. The location is fantastic for touring Chicago. The neighborhood is beautiful with lovely architecture and interesting shops. There are lots of families; couples walking, biking, babies-buggying. We enjoyed walking around the neighborhood after a walk to dinner or lunch. The bed/bedding is very comfortable and we slept very well. Great temp control, lots of windows, and a 65"flat screen TV. The bathroom is large and airy with a walk-in shower. The unit is very quiet, with dual-pane windows and black-out shades for sleeping in late. Stay here for the best Chicago experience.
Guest favourite
Flat in West Town
4.96 out of 5 average rating, 28 reviews

Newly Remodeled in West Town

ShreyaRating, 5 stars1 week ago
Sarah’s place was lovely! We had a wonderful time — it was within walkable distance to main attractions, and the neighborhood itself was safe, nice, and clean.
Top guest favourite
Flat in West Town
5 out of 5 average rating, 30 reviews

Bosworth Living in Wicker Park

DylanRating, 5 stars1 week ago
Super awesome space, me and my wife had a blast and felt the neighborhood we were in was super easy to explore.
Guest favourite
Flat in Logan Square
4.92 out of 5 average rating, 553 reviews

2BR Bursting w/ Character in Hip Logan Square!

LauraRating, 5 stars3 weeks ago
Danielle's place was cozy and clean. The back yard had table and chairs and private so we could sit outside. It was close to CTA and we could walk to so many places—great location with restaurants and bars. I would recommend staying at her place.
Top guest favourite
Flat in Logan Square
4.95 out of 5 average rating, 218 reviews

Tastefully designed 1500 Sq of Homeyness!

LauraRating, 5 stars1 week ago
Kath’s place is super convenient to wicker park and bucktown vintage shops, coffee and restaurants. A great layout and plenty of room. Extremely clean! Close enough to the city but a nice quiet neighborhood in the evening. Would love to visit here again!

Private apartment rentals

Guest favourite
Flat in Wicker Park
4.86 out of 5 average rating, 21 reviews

Cozy Apartment in Prime Wicker Park!

KevinRating, 5 stars1 week ago
We visited Wicker Park to help move our daughter in to an apartment. Patricia 's place was within a few minutes walking distance. The pictures of Patricia 's place were accurate. We found it to be very charming and clean. What we appreciated the most was the proactive communication. We would definitely stay here again and recommend it to others .
Top guest favourite
Flat in West Town
4.95 out of 5 average rating, 434 reviews

A Vintage Pink House in the Heart of Chicago

JessicaRating, 5 stars4 days ago
Niki's place is located close to multiple bus and CTA lines which made exploring Chicago so easy. The bed was great - lovely sheets, great mattress and pillows were awesome. You don't always get that! Niki and her husband, Sean were so helpful and communicative. Being able to stay at their place really helped make our celebration weekend easy and fun.
Top guest favourite
Flat in Chicago
4.99 out of 5 average rating, 232 reviews

Modern Apt with style & comfort in Pilsen Chicago

AnthonyRating, 5 stars2 days 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
Superhost
Flat in West Town
4.79 out of 5 average rating, 48 reviews

Logan Square Oasis

MichaelRating, 5 stars6 months ago
Really liked the neighborhood. Was a short walk to the blue line. The place was perfect and will come back 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 stars5 days 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.
Guest favourite
Flat in Logan Square
4.88 out of 5 average rating, 320 reviews

Logan Square Video Game Loft

ChristopherRating, 5 stars1 week ago
Great building, super fun neighborhood easy to walk to everything. Great spot to be out late at night. Definitely worth booking.
Guest favourite
Flat in Wicker Park
4.9 out of 5 average rating, 52 reviews

Pierce Place in Wicker

JaneRating, 5 stars2 days 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 Wicker Park
4.98 out of 5 average rating, 48 reviews

Stylish 2-Bedroom Wicker Park Apartment

NenaRating, 5 stars4 days ago
Very nice apartment in a nice neighborhood. The pictures are true to reality. The bedrooms and bathrooms are small and we had to keep our suitcases in the living room and hallway. There was a decent size closet in each bedroom with hangers and shelves. The beds and beddings were comfortable. The apartment is within short walking distance from many good places to eat.

Apartment rentals with a hot tub

Superhost
Flat in The Loop
4.92 out of 5 average rating, 48 reviews

The Areal Oasis

JenniferRating, 5 stars3 weeks ago
What a spectacular stay! We thoroughly enjoyed our time at Stephanie's "Areal Oasis". Apartment was spotless, well decorated, very well furnished, and the view is spectacular. Stephanie was an excellent communicator and always very responsive. We thoroughly recommend staying here and hope to return.
Superhost
Flat in West Rogers Park
4.85 out of 5 average rating, 78 reviews

Spacious Beautiful Condo

SophiaRating, 5 stars2 days 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
4.83 out of 5 average rating, 54 reviews

Rooftop HotTub As Seen On "Married At First Sight"

KimikoRating, 5 stars8 months ago
I booked this Air BNB for my girlfriend's birthday weekend and my surprise proposal! Ashlee was very responsive, super helpful, just an overall great host! She went out of her way to decorate the master bedroom for me with rose petals, tea lights, champagne and all! There were snacks in the kitchen, the place was clean and tidy, our group really felt at home! The vibes were everything, and so were the VIEWS from the rooftop!!!! Thank you Ashlee!!
Guest favourite
Flat in West Loop
4.96 out of 5 average rating, 27 reviews

Skyline Oasis: City & Lake Views

NatalieRating, 5 stars2 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 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.
Top guest favourite
Flat in West Town
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars4 weeks 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.
Guest favourite
Flat in Near North Side
4.92 out of 5 average rating, 38 reviews

Lincoln Park Haven: Balcony, Walk to Whole Foods

KristenRating, 5 stars3 days ago
Loved our stay at The Foundry! The unit was beautiful and comfortable and the views were incredible. We had everything we needed and communication from Cloud9 was clear. There are great places nearby to walk for coffee and food — including an amazing Whole Foods.
Superhost
Flat in The Loop
4.69 out of 5 average rating, 49 reviews

Sentral 1 Bedroom Apt in South Loop Chicago

RichardRating, 5 stars1 week 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.

Quick stats about flat rentals in Wicker Park, Chicago

  • Total rentals

    90 properties

  • Nightly prices starting at

    ₹3,471 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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