
Apartment holiday rentals in Wicker Park
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Top-rated apartment rentals in Wicker Park
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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

Gorgeous Penthouse with Stunning Views from Private Rooftop
Welcome! We are young professionals opening up our 2 bedroom apartment to warm and down-to-earth travelers. We'd like to help you fall in love with Chicago! LIVING SPACE: Top floor condo with a great view of the neighborhood tree-lined street. Moderately large open space with hardwood floors, a comfortable and inviting atmosphere, and plentiful natural light. You can also relax on our private rooftop. KITCHEN: You are free to use the full kitchen. BEDROOMS: Two bedrooms with ample natural light and large closets. Fresh sheets, pillow, bath soap, and bath towels will be provided. BATHROOMS: 2 bathrooms (1 is a master bathroom with shower and bathtub) for guests. Central A/C is provided in the warm months and central heat during the cooler months. We live in Chicago and are happy to help if you need something. Beautiful walking-friendly Wicker Park showcases Chicago's culture, arts scene, and food and entertainment. Explore diverse nightlife and bars, historic buildings, countless vintage shops and boutiques, and street festivals in the warmer months. TRANSPORTATION: The condo is approximately a 30+ minute direct train ride from O'Hare airport and ~40+ minute train ride from Midway airport (1 transfer) using the "El" train. Getting to our condo from O'Hare is direct as we live right off the 'DIVISION' stop on the BLUE LINE. From Midway, you would need to transfer from the ORANGE LINE to the BLUE LINE. We are a fairly quick train or bus ride to the Loop and River North (for access to "downtown" cultural and city attractions) as well as other popular Chicago neighborhoods such as Ukrainian Village (walking distance), Bucktown (walking-bike distance), Gold Coast, Old Town (1 single bus, no transfers), Greektown, West Loop (quick Uber), Lincoln Park, Lakeview (bus), and Logan Square (quick "El" train ride). PARKING: Free parking can be found on Augusta Blvd (with exceptions on certain hours/days for street cleaning). Additional free parking can be found just a bit further on Cortez and Paulina. We look forward to providing you with the Wicker Park and Chicago neighborhood experience. Once you arrive, you'll get an even better picture of how phenomenal this location is.

CUTE, PRIVATE & QUITE STUDIO 1BD/1BA Wicker Park!!
Grateful location, Wicker Park has everything nearby based on walkability to explore! Many boutique shops, a number of coffee shops and locally own restaurants and bars. A 2 minute walk to CTA Blue Line subway excess to downtown Chicago, Lake, Museums or to O’Hare Airport and Midway Airport. SPACE: Entrance to building, very welcoming. Stairs and hall very clean, have laundry area coin washers and dryer (if needed). Studio very clean, professionally, to ensure the wellness to our guest's

Chic City Escape | 2BR Retreat w/ Parking.
PRIME LOCATION -heart of Wicker Park: Clean, modern, and eccentric condo with 11 ft ceiling, brick wall, and lots of natural light! Our home is in the heart of Wicker Park- one minute walk to the busy Milwaukee street bustling with restaurants, cafes, bars, shops, and theaters. The condo is a five minute walk away from the Damen Blue Line allowing easy access to the city and to O’Hare airport. We’re also a 12 minute drive to beautiful Lake Michigan. Early checkin/late checkouts upon availability

Spacious Studio w/Balcony in Bucktown/Wicker Park
My place is in the heart of one of Chicago's Hottest and Hippest neighborhoods(Wicker Park/Bucktown) with everything you need or want within a short walk - Transportation(Blue Line Train) which is a direct shot to and from O'hare airport, Dining, Nightlife, High End boutique shopping. 15 minutes to the Magnificent Mile, Millennium Park, Wrigley Field. Perfect for couples, solo adventurers, and business travelers with Internet and Cable TV included. Sleeps 2 adults comfortably w/sleeper sofa.

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.

Wicker Park Walk-Up Condo
Enjoy the best of what Chicago has to offer. Located in the West Town/Wicker Park Neighborhood, steps away from the exciting Division St. and Milwaukee Ave. lined with great neighborhood bars, restaurants, boutiques, etc. Centrally located steps from public transit (The "L" Train/Bus), the expressway, Goose Island, Lincoln Park, & More. Experience one of Chicago's best and most interesting neighborhoods! This apartment is fully furnished with modern touches, a private rear deck & front patio.

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.

Colorful Bucktown Garden Apartment
Enjoy a stylish experience at this centrally-located apartment. Close to all of the neighborhood amenities including the 606 trail, shopping district, highly reviewed restaurants, blue line "el" train, neighborhood parks, and more. Walk to everything you need or jump on the blue line to get downtown quickly. Our colorful space is perfect for your city stay. Enjoy comfortable spaces including an oversized bedroom, cozy living room, fully appointed bathroom, dining area, and a kitchenette.

【Central】- Eclectic Fun 1BR APT in Wicker Park
Located in the heart of Wicker Park! Just a 5-min walk from the CTA blue line Damen station. This bright second floor 1-bedroom, 1-bath apartment allows you to access EVERYTHING Chicago has to offer all within short walking distance, with great nightlife. Just walk downstairs, you will find trendy restaurants, cocktail bars, cozy coffee shops and a variety of shops in this popular neighborhood. Want to explore downtown? Uber/Lyft or Hop on the CTA "L" train to go anywhere in the city.

Strictly Commercial Storefront: Humboldt, Bucktown
Enjoy a private entrance to your street-level storefront apartment at the intersection of Bucktown, Wicker Park, Humboldt Park and Logan Square neighborhoods. Easy access to transport. Rest in comfort and check out the 606 elevated trail, Humboldt Park, restaurants, shopping, and nightlife. Well-outfitted apartment features exposed brick, unique lighting, and lofted bedroom. Anthropologist? Watch the street scene through one way glass. You can see out, but your subjects can't see in.

Hip Chicago Condo in fun shopping and dining area
Spacious 2 bedroom, 2 bath condo in ideal Wicker Park location-walk to everything including CTA/Blue Line, shops, restaurants & Division St. Night Life!! Highly upgraded with hardwood floors, granite countertops & breakfast bar, SS appls, luxurious marble baths, Jacuzzi tub & wood burning fireplace. This condo also features a large walk-in-closet, washer and dryer, private outdoor covered terrace. Free street parking. *Send PM for one night stays
Popular amenities for Wicker Park apartment rentals
Weekly apartment rentals

A Vintage Pink House in the Heart of Chicago

Vintage Ukrainian Village Apartment

The Bucktown House - Damen Suite - Since 2008

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Urban Oasis with Skylights and Cozy Queen Beds

Logan Square Apartment!

The Noble Farmhouse, w/ Garden in West Town

Sunny Wicker Park Apartment - 2BR with Deck
Private apartment rentals

Modern 3BR with Private Rooftop & Free Parking

Wicker Park Top-Floor Private Balcony Views

Pristine Chicago Home | 3BD |2BA |Free Parking (2)

The Bell House: Apartment #1

WickerPark 3BR| 5beds|2 Parking| Damen L 4-minute walk

Large 3BR/2BA Wicker Park Apt +Free Garage Parking

Penthouse In Wicker Park

The Mason - Luxe 2BR Designer Flat in Bucktown/WP
Apartment rentals with a hot tub

Top Floor Views + Central Comfort

Level Junior Two Bedroom Suite | Fulton Market

Super Paradise+65 Amenities*Downtown 15 Min

Luxury 3BD Penthouse – Private Patio+Skyline Views

Skyline Oasis: City & Lake Views

Chic 1 BR w 1 G Parking| W Park Nightlife nearby

Belmont Pleasures - hot tub / arcade gaming room

420 friendly apt with 2 queens,1 full,1 twin bed
When is the best time to visit Wicker Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $143 SGD | $144 SGD | $172 SGD | $172 SGD | $203 SGD | $206 SGD | $211 SGD | $218 SGD | $209 SGD | $210 SGD | $176 SGD | $168 SGD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about flat rentals in Wicker Park

Total holiday rentals
Explore 90 holiday rentals in Wicker Park

Nightly prices starting at
Wicker Park holiday rentals start at $25 SGD per night before taxes and fees

Verified guest reviews
Over 6,180 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
90 of Wicker Park holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Wicker Park rentals

4.8 Average rating
Wicker Park stays are highly rated by guests – averaging 4.8 out of 5!
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Garfield Park Conservatory
- Brookfield Zoo
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- University of Chicago
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower




