Apartment holiday rentals in Wicker Park, Chicago

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Popular amenities for Wicker Park, Chicago apartment rentals

Weekly apartment rentals

Guest favourite
Apartment in Ukrainian Village
4.92 out of 5 average rating, 197 reviews

iKlektik House Chicago / BlueJay

ARating, 5 stars2 weeks ago
We really enjoyed our stay here! Perfect for two people. This place is really cute and unique. Love the decor and seeing all the cool art projects. This place was within a couple miles of all the places we wanted to see, especially Soldier Field, so a Uber/taxi ride was cheap and very convenient. Super cute neighborhood too with beautiful row houses both modern and original. It is a nice quiet neighborhood as well and we felt very safe! We would recommend the Iklektik/Blue Jay house to anyone visiting Chicago that wants a comfortable and cozy experience!
Guest favourite
Apartment in Logan Square
4.96 out of 5 average rating, 298 reviews

Logan Square 2nd Floor Chicago Victorian

JaspreetRating, 5 stars3 weeks ago
We had an amazing stay at Kitty’s place! From the moment we arrived, she made us feel so welcome. She even decorated the house for my fiancée’s birthday and left us treats, which was such a sweet touch. Her recommendations were super helpful and made our trip even better. The house was full of books and art that made it feel really special, and the beds were super comfy. The separate entrance was great for privacy, and street parking was easy to find, which was a big plus. Thank you so much for all the little things that made our stay unforgettable. We would love to stay here again very soon!
Guest favourite
Apartment in Avondale
4.97 out of 5 average rating, 160 reviews

Designer Avondale Attic

ChristopherRating, 5 stars3 weeks ago
One of our favorite Airbnbs in Chicago, it has a great central location and great street parking (with a permit). It's cute. clean, and quiet. I highly recommend!
Guest favourite
Apartment 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.
Superhost
Apartment in Wicker Park
4.96 out of 5 average rating, 142 reviews

Hip 3 BR in Heart of Historic Wicker Park!

BenjaminRating, 5 stars2 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).
Guest favourite
Apartment in West Town
4.97 out of 5 average rating, 208 reviews

The Noble Farmhouse, w/ Garden in West Town

JoanRating, 5 stars3 weeks ago
Lovely home! Clean, stylish and comfortable. We appreciated the close proximity to great restaurants such as Engine Coffee and Flo. I got in touch with my Polish roots at the Polish Museum of America down the block. They have an intact exhibition from the 1939 World’s Fair Polish Pavilion. Also visited Holy Trinity Church where all the services are in Polish. If you are interested in the rich history of this neighborhood you might check these places out.
Guest favourite
Apartment in Wicker Park
4.85 out of 5 average rating, 177 reviews

Authentic Wicker Park Home | Walk to Everything.

KelseyRating, 5 stars3 weeks ago
This was a wonderful place to stay! Great neighborhood and so close to the train station easy to jump on and get to the heart of downtown! Love the place and was perfect for what we needed!
Guest favourite
Apartment in Logan Square
4.9 out of 5 average rating, 101 reviews

Bright & Cozy 1-Bedroom Apartment in Logan Square

SarahRating, 5 stars4 days ago
Very clean and peaceful place to stay. Loved the space and location!!

Private apartment rentals

Top Guest favourite
Apartment 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
Apartment in West Town
4.99 out of 5 average rating, 83 reviews

Humboldt Park Retreat: Skylights & Queen Beds

PageRating, 5 stars1 week ago
Such a beautiful, cozy space! Very comfortable beds, the perfect coffee setup and fast WiFi gave us the ability to work and play. Plus our host was incredibly responsive and communicative. Would definitely stay again!
Top Guest favourite
Apartment in Ukrainian Village
4.93 out of 5 average rating, 223 reviews

Spacious & Clean Ukrainian Village 2 Bedroom!

SusanRating, 5 stars3 weeks ago
I hesitate to say how I really feel because I’d love to keep this gem all to myself. Such a cute place and a wonderful neighborhood. Hoping to stay there again!
Top Guest favourite
Apartment in Lincoln Park
5 out of 5 average rating, 263 reviews

Explore Lincoln Park from a Polished Apartment

KatieRating, 5 stars1 week ago
You can believe the hype of the great reviews. Beth’s place has everything I want in an Airbnb. The decorations were thoughtful, there’s coffee and a full kitchen and a great shower and so many windows - all with black out blinds for night. Plus, the area is fantastic. I went on great neighborhood runs and it’s a quick straight shot to the lake too. Plus, the bus downtown is on the corner and really easy to navigate. Oh! And she left cookies for me! Thank you thank you, Beth!
Guest favourite
Apartment in Logan Square
4.91 out of 5 average rating, 160 reviews

Cozy 1BR in the heart of Logan Square

SydneyRating, 5 stars2 weeks ago
Nikka was very kind and communicative, and she made our stay super simple and enjoyable! We were here for a concert at Soldier Field and it went super late, so having easy access to a train station as well as many late night food options was especially helpful. If I'm ever coming back to the area I would definitely stay here again!
Superhost
Apartment in Wicker Park
4.89 out of 5 average rating, 9 reviews

The Bucktown Nook | Near Transit w/ Free Parking

AnnRating, 5 stars1 week ago
We loved staying in this stylish Bucktown apartment - easy to check in and out, very comfortable bed and furnishings, and super convenient to the blue line.
Top Guest favourite
Apartment in Logan Square
5 out of 5 average rating, 56 reviews

The Heart of Bucktown

ToniRating, 5 stars1 week ago
This place is as described. Very clean. The sofa was very comfortable. Nice little local bar at the end of the block. Very cute neighborhood. Only con, is if you are a light sleeper the ceiling fan in the bedroom is a bit noisy. It didn't bother me while sleeping but it's noticeable when awake.
Superhost
Apartment in Logan Square
4.86 out of 5 average rating, 122 reviews

Private Garage+Laundry+Restaurant Row+93 Walkscore

EmilyRating, 5 stars1 day ago
Another great stay! Eva is a great host and ensured that everything was well stocked and ready for my stay. The location was great for outdoor running, just a block from an entrance to the popular 606 Trail. 5 stars!

Apartment rentals with a hot tub

Superhost
Apartment 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
Apartment in West Rogers Park
4.84 out of 5 average rating, 77 reviews

Spacious Beautiful Condo

KristinRating, 5 stars2 weeks ago
Perfect location for a family to stay that’s close to everything. We did days in the city and a game at Wrigley. Very clean and perfect for our long weekend in Chicago.
Superhost
Apartment in The Loop
4.67 out of 5 average rating, 311 reviews

Sentral Premium 2BR Apt South Loop Chicago

YvetteRating, 5 stars2 weeks ago
It was a great place to stay definitely felt like home! I went for the weekend and the restaurants around there were great. They communicated very well when I had questions and responded with good time. Thank you and I’ll see you next year! :)
Superhost
Apartment in Lake View
4.7 out of 5 average rating, 10 reviews

Minutes to Wrigley Amazing Location - Sleeps 6

MattRating, 5 stars1 month ago
Freddy was an incredibly friendly and responsive host, really went above and beyond to ensure a good trip. The location is perfect, just a few minute walk to everything you could want while still maintaining a quiet residential feel.
Superhost
Apartment 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!!
Superhost
Apartment in Chicago
4.88 out of 5 average rating, 16 reviews

Large Studio Apartment with no cleaning fee

Latrice Rating, 5 stars3 days 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.
Guest favourite
Apartment in West Loop
4.96 out of 5 average rating, 26 reviews

Skyline Oasis: City & Lake Views

RobertRating, 5 stars4 weeks ago
Beautiful view of the city. The location is perfect! It is close to the train station and easy for Uber to get in and out of. Lots of restaurants, coffee, gelato, cookies, and donuts within walking distance. Our host was very responsive and quick to answer any questions we had and even provided restaurant suggestions. The balcony view is amazing day or night with the city scape and a view of the lake.
Top Guest favourite
Apartment in West Town
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars3 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.

Quick stats about apartment rentals in Wicker Park, Chicago

  • Total rentals

    90 properties

  • Nightly prices starting at

    $61 AUD 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

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