
Apartment holiday rentals in Wicker Park, Chicago
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Top-rated apartment rentals in Wicker Park, Chicago
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Popular amenities for Wicker Park, Chicago apartment rentals
Weekly apartment rentals

City View 3BR Condo/Garage Parki
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.

Picture Perfect 3Bed Steps from Train and FLW
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!

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.

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

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!!

Cozy 1bdr Rogers Park, Loyola, Northwestern.
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.

2-Story Luxury Condo in Wicker Park–10 Mins to DT
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.

Lincoln Park Hideaway - 5 Min Walk to the Park!
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

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
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.

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!
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.

Spacious & Stylish Home at the ♥ of Wicker Park
Great place for a large group to share a space. Lovely neighborhood, nice apartment, and Joe was very responsive.

Large Remodeled Home in Lincoln Park, Sleeps 12!
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.

Modern Luxury In Old Town - Sleeps 4
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!

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

"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.

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

voco: Balcony & City View
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.

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony
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.

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.
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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- 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
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Moraine Hills State Park