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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

Superhost
Apartment in Wicker Park
4.87 out of 5 average rating, 38 reviews

City View 3BR Condo/Garage Parki

ManuRating, 5 stars5 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
Apartment 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!
Top guest favourite
Apartment 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
Apartment in Humboldt Park
4.93 out of 5 average rating, 61 reviews

Amazing Fun Condo, City view next to 606 Trail!

JasonRating, 5 stars1 day ago
If you have the opportunity to stay at Ken’s Airbnb, take it! It was a great experience, a unique property that is as fun as it is comfortable! Ken was an outstanding host, incredibly flexible, super responsive and willing to provide suggestions for our unique parking circumstances. We would stay again anytime! Thanks Ken!!
Guest favourite
Apartment 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!!
Guest favourite
Apartment in East Rogers Park
4.93 out of 5 average rating, 241 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
Apartment 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 stars4 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.
Superhost
Apartment in Old Town Triangle
4.88 out of 5 average rating, 155 reviews

Lincoln Park Hideaway - 5 Min Walk to the Park!

JaclynRating, 5 stars5 days ago
My family and I loved our stay; the apartment was adorable and had everything we needed. But the location is truly the highlight! Walking distance to North Ave beach, Lincoln Park Zoo, all the fun restaurants and shops in Old Town, and the famous Second City Comedy Club.

Pet-friendly apartment rentals

Superhost
Apartment in North Side
4.83 out of 5 average rating, 362 reviews

Chic and Charming Vintage Condominium in Lincoln Park

PatrickRating, 5 stars3 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
Apartment in Lake View
4.99 out of 5 average rating, 178 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

RonniRating, 5 stars2 days ago
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.
Superhost
Apartment in Chicago
4.87 out of 5 average rating, 119 reviews

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

AlfredoRating, 5 stars3 weeks ago
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.
Guest favourite
Apartment in South Side
4.92 out of 5 average rating, 166 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

WilliamRating, 5 stars1 week ago
Crazy clean, super breezy place to stay. Neighborhood is fine, but not a lot of amenities. But it was a great place for us to be.
Guest favourite
Apartment in Wicker Park
4.88 out of 5 average rating, 265 reviews

Spacious & Stylish Home at the ♥ of Wicker Park

TimRating, 5 stars2 days ago
Great place for a large group to share a space. Lovely neighborhood, nice apartment, and Joe was very responsive.
Guest favourite
Apartment 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
Apartment in Lincoln Park
4.78 out of 5 average rating, 226 reviews

Modern Luxury In Old Town - Sleeps 4

MargaretRating, 5 stars2 days ago
We had a great stay. We love this area of Chicago so we were so pleased with the location. Robert is very responsive and was a great host!
Guest favourite
Apartment in Uptown
4.97 out of 5 average rating, 124 reviews

Large 2BR, 2BA, patio, sunroom, W/D, L-kitchen

SusanRating, 5 stars2 weeks ago
Pablo was an incredibly responsive and helpful host, even volunteering to have us check in early. His place was spacious (can accommodate 4-5 people) and comfortable. . . really a home away from home. Had everything we needed for a 5-day stay . . washer/dryer a plus! Parking can be a challenge, but using SPOT Hero helped us identify available spots. While next to the train, the train noise was more like white noise and did not disturb us. Would definitely stay again!

Apartment rentals with a pool

Guest favourite
Apartment 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
Apartment 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.
Apartment in River North
4.45 out of 5 average rating, 11 reviews

voco: Balcony & City View

AmitRating, 5 stars2 weeks ago
gorgeous views and very nice condominium. great balcony and very safe. The elevators were super fast. Even though the actual location is different than the one mentioned in listing, it still wasn't disappointing. There is enough space for a small family or a couple.
Apartment in Lombard
4.84 out of 5 average rating, 56 reviews

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

LelandRating, 5 stars5 months ago
Briana was responsive before, during and immediately after our stay, always seeking to ensure our comfort and satisfaction. We would have no reservations about staying with them again if they have an opening during a future visit to the area.
Apartment 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
Apartment 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
Apartment in Evanston
4.91 out of 5 average rating, 126 reviews

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

FeiRating, 5 stars4 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.
Guest favourite
Apartment 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 apartment rentals in Wicker Park, Chicago

  • Total rentals

    30 properties

  • Nightly prices starting at

    $64 SGD 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

  • Wifi availability

    30 properties include access to wifi

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