Apartment holiday rentals in Wicker Park, Chicago

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Top-rated apartment rentals in Wicker Park, Chicago

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Guest favourite

Apartment in Wicker Park

4.97 out of 5 average rating, 236 reviews

Stylish First Flr. Studio. Best Location Division+Hermitage.

Clean! Private! Studio located in the popular Ukrainian Village. This quiet unit is located in a charming 19th century pink brick Victorian cottage. It is a great retreat from work or play when visiting Chicago. This welcoming space features modern amenities, stylish decor with unique artwork, tall ceilings and an inviting color palette. Hermitage House Studio a perfect home away from home with in unit laundry, cable with On Demand and green filled backyard patio perfect for sipping your morning coffee or tea. Need 2nd space same building? Check out airbnb.com/h/chicago-hermitage-loft2 This private –very hip studio apartment - completely renovated and newly decorated is set up like a posh hotel suite with all the amenities of home!! Used for guests only this cozy and modern first floor apartment is set in an 1892 vintage brick cottage with a beautiful outdoor rear patio on a quiet tree lined street! This richly colored designer decorated space with all original artwork has comfort in mind. It has plenty of seating including a comfortable leather sofa, a cool desk area and raised bar. Hardwood floors throughout living space, 9’ ceilings, washer/ dryer, central air and heating, hotel like bathroom with soaking tub and an in unit stacking washer/dryer. Modern white kitchen has granite countertops, quartz sink, gas stove-oven, dishwasher, garbage disposal , microwave. The kitchen has many fun gadgets like French press coffee maker, electric tea pot and more. Everything is available for you to use. The high counter with barstools separates the kitchen from the living/sleeping space. The relaxing bedroom area accommodates 2 with a queen pillow top Serta mattress, great lighting, beautiful Mediterranean blue curtains and storage end tables filled with additional blankets. A full aero bed can accommodate a third person if needed. There is a custom closet system with great storage for personals, shoes and folded clothing. Perfect for a couple or an Airbnb business user! Flat screen TV with cable and movie channels Fast Wi-Fi This unit is located in the quiet first floor rear of this building. The first floor rear patio is yours to enjoy! The upper level deck is private. This unit features a digital locks. You will be able to pick your own code before check-in. I am readily available but will respect your privacy unless you need me. I live in the building (Sometimes out of town) but always accessible by phone or internet if anything is needed but the place is yours to enjoy! Located just steps off bustling Division Street this neighborhood has it all without the fuss of downtown. Within walking distance there are restaurants with cuisines from around the world as well as comfort food. Nightlife options including live music and sports venues. There is boutique shopping, art galleries, a local gym and even a mini Target. This cozy Studio is quick walk from the Division St. Blue-Line train that will get you downtown or to O'hare Airport in minutes. Just two blocks to the Division Blue line running from O’Hare and downtown at the intersection of Division/Ashland/Milwaukee This is a great walking neighborhood but it is easily accessible to many buses, cabs, trains and even the new shared Divvy bike station just a block from the studio. If you choose to drive there is zoned parking permits available- 1 per day. I will happily provide directions to attractions, neighborhoods, great food, groceries, coffee and nightlife

4–11 Jan

$356 NZD per night

Guest favourite

Apartment in Chicago

4.92 out of 5 average rating, 326 reviews

Bright, Modern Apartment in a Vintage Greystone

Enjoy morning coffee by the sunny bay window in this vintage apartment with classic modern style. The apartment features vintage charm with modern amenities, queen memory foam bed in bedroom and queen sofa bed in living room. Parking is available in the back lot for an additional $25 per night. For reservations over three weeks, we require a cleaning every 2 weeks at a cost of $60 per cleaning. Apartment is located on the 3rd floor of a three story building and you will need to climb stairs. This is a large 1100 square foot fully renovated 1 bedroom apartment on the third floor of a beautiful vintage Chicago Grey Stone. Located directly on Chicago Ave. The space was thoughtfully designed by the design firm of Inside Home with the modern traveler in mind. The furnishings are a mix of vintage and new pieces specially curated for the space. The bedroom features a queen memory foam mattress as well as a 42" TV. The kitchen is equipped with cutlery, cooking utensils, coffee maker, espresso machine, pots & pans, baking sheets. Walking Rating of 96! You will have access to the full 1100 square foot apartment as well as a parking spot if needed located directly out back for an additional $20 per night, please notify us at the time of booking if you will require parking and we will add this fee to your reservation. There is also a washer and dryer in the basement if need (please request access) We will be on site at the furniture store located on the ground floor of the building should you need anything during your stay. Ukrainian Village is a historic community known for the contemporary restaurants, bars, and shops along bustling Chicago and Division Streets, but explore the neighborhood further to discover homes and businesses as old as the city itself. You are steps away from the 66 bus, which will take you directly to Navy Pier, rent a bike and explore the city or catch a cab right out side the front door or jump on the blue line "EL" train. This apartment has a walk rating of 96, bike rating of 90 and a transit rating of 72! This apartment is located on the third floor of a three story walk up. There is a additional queen bed in the sofa of the main room and all the additional bed linens are located in the bedroom night stand and closet.

9–16 Nov

$342 NZD per night

Guest favourite

Apartment in Wicker Park

4.96 out of 5 average rating, 247 reviews

Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!

Located in the heart of Wicker Park, just a 5 min walk to the Damen blue line stop. This phenomenal location allows you to access EVERYTHING Chicago has to offer without having to rent a car. Experience the best of Chicago, all within a short walk from your stay. World class bars, restaurants, and shopping all within walking distance. Want to explore downtown or catch a Cubs game at Wrigley? Hop on the "L" train and use the CTA to go anywhere in the city. This cozy garden apartment has it all.

23–30 Oct

$423 NZD per night

Guest favourite

Apartment in Chicago

4.96 out of 5 average rating, 100 reviews

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Location! Location! Location! Prime Wicker Park Location on Milwaukee! This spacious, cool, vibrant, eclectic, fully equipped apartment is close to everything, making it easy to plan your visit. Bright top floor unit with a private patio to just chill and unwind or walk downstairs and your literally in the heart of Wicker Park. Super easy access to downtown nightlife/lake/museum all within 15 minutes and super easy commute to O'hare. CTA busses all around and a 2 minute walk to the Blue Line.

9–16 Sep

$545 NZD per night

Guest favourite

Apartment in Humboldt Park

4.98 out of 5 average rating, 107 reviews

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

20–27 Oct

$274 NZD per night

Guest favourite

Apartment in West Town

4.96 out of 5 average rating, 120 reviews

Cozy Urban Getaway East Village Apartment

Cute, airy space ideal for singles or couples traveling to Chicago for a fun weekend...or a month! Walkable to hip eateries/tacorias/ bars, yummy coffee shops, boutique grocery stores, open parks--and less than a mile from the Blue Line--which can take you to O'Hare Airport or downtown. Designer kitchen is fully stocked with all you would need for an easy night in. Living room features comfy couch and local artists' work. Guests report this is one of the best showers they've experienced!

9–16 Dec

$380 NZD per night

Superhost

Apartment in Wicker Park

4.78 out of 5 average rating, 219 reviews

Private Studio Apt in the Heart of Wicker Park!

*No Hidden Cleaning Fees or Deposits* Enjoy Wicker Park with your own private renovated studio apartment! This large studio is on the corner of Wood St & Le Moyne St. The apartment comes complete with a large living space, pull out couch bed, kitchenette with fridge & microwave, air conditioning, wifi, TV, new bathroom, laundry facilities, and a communal rooftop deck with skyline views. Close to EL train, highway, shopping, restaurants, nightlife, cafes, 606 bike trail and more!

23–30 Mar

$277 NZD per night

Guest favourite

Apartment in West Town

4.96 out of 5 average rating, 262 reviews

Turquoise Wonder - Clean, Cozy & Stylish Apt

Clean, stylish & comfy apartment, perfect for 1 or 2 adults. 2 guest maximum, no children. Close to public transit (bus), wonderful restaurants & bars, gift shops, boutiques, coffee shops, parks, museums & more. Ukrainian Village/Humboldt Park area. King size comfortable Tempurpedic mattress. Central heat, A/C. Nice kitchen w/ stainless appliances, excellent bathroom, shower & tub. Free street parking. Relax in the comfort of the Turquoise Wonder! Enhanced cleaning protocols for COVID.

21–28 Apr

$242 NZD per night

Guest favourite

Apartment in Logan Square

4.85 out of 5 average rating, 184 reviews

Bucktown Retreat - Why The Buck Not? Sleeps 1-6

Located in historic Bucktown, this 2 bedroom first floor condo has all the comforts and charm you'd expect and more. Need to work? Play? Relax? Easy access to/from the Loop/O'Hare? Our location has the best of what you are looking for. Located within a quiet street of Bucktown, you can hop skip and jump out the door to an ecclectic variety of local eateries, coffee shops, bars, shops, arts, amusement, and outdoor life. Let our place be your Bucktown Retreat - Why the Buck Not?

10–17 Dec

$296 NZD per night

Superhost

Apartment in Wicker Park

4.81 out of 5 average rating, 370 reviews

WESTERN AVE ARTISTS LOFTS- Park Free

FREE street PARKING. Walk to Wicker Park restaurants, bars & shopping. 10 MINUTE WALK to CTA Blue line TRAIN-Damen stop. Premium queen mattress ( small bedroom but has a queen bed) & brand new sofa bed. Full kitchen & washer & dryer in apartment. Resident artists work on first floor of this historic former telephone repair and switching station. Very laid back vibe. EVERYONE is Welcome.

16–23 Oct

$241 NZD per night

Guest favourite

Apartment in West Town

4.89 out of 5 average rating, 473 reviews

iKlektik House Chicago / Robin

CLOSE TO THE UNITED CENTER! Bright, Sunny and Stylish one bedroom, full kitchen, balcony over looking the backyard in West Town WITH FREE STREET PARKING. Close to Wicker Park, Ukrainian Village West Town and Bucktown. The space is amazing...just read the reviews! Very cozy! There is FREE street parking. WiFi Speed has been upgraded to 1200mps!!

24–31 Dec

$307 NZD per night

Guest favourite

Apartment in Logan Square

4.93 out of 5 average rating, 207 reviews

Cozy Private Coach House

This is a cozy 1 bedroom unit in a private coach house. Excellent location in the middle of trendy Logan Square! Please Inquire about winter time longer stays! Stays 30+ days avoid local taxes! I have a 28 night minimum in the winter, until the end of February or possibly March. But I recommend putting in at least 30 days to avoid those taxes!

15–22 Oct

$311 NZD per night