Holiday houses in Wicker Park, Chicago

4.82 out of 5 average rating, 442 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 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. All guests must be on the reservation for $total. Note $30 per night per guest charge AFTER 2 Guests ( 3&4)

5 out of 5 average rating, 120 reviews

Beautiful, Clean 2BD/1BA/parking;Centrally located

PRIME LOCATION & FREE Parking in the Unit: 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 availab

4.94 out of 5 average rating, 140 reviews

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.

4.94 out of 5 average rating, 326 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.

4.96 out of 5 average rating, 151 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.

4.98 out of 5 average rating, 103 reviews

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.

Superhost

4.93 out of 5 average rating, 109 reviews

【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.

Apartment in Noble Square

4.97 out of 5 average rating, 536 reviews

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

4.97 out of 5 average rating, 246 reviews

Home in Wicker Park

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

4.95 out of 5 average rating, 127 reviews

Apartment in Bucktown

BRAND NEW Elegant Renovation in Bucktown (Chicago)

Elegant, newly renovated 1 bedroom apartment nestled in the trendy Chicago neighborhood of Bucktown. Our home is the perfect place for you to stay while you explore the city. Located just a few blocks away from vibrant Bucktown restaurants, live music, bars, 606 city trail, and downtown. The Damen blue line subway station is about 10 minute walk from the apartment, giving guests easy access to O’Hare and the rest of the city. Free street parking is also available.

4.97 out of 5 average rating, 154 reviews

Cozy Urban Getaway East Village Apartment

Cute, airy space ideal for singles or couples traveling to Chicago as digital nomads or an extended stay! 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 ready for you! Living room features comfy couch and local artists' work. Guests report this is one of the best showers they've experienced!

4.95 out of 5 average rating, 107 reviews

Condo in Wicker Park

Modern Izakaya Studio in Wicker Park

Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

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Other great holiday rentals in Wicker Park, Chicago

Apartment in Humboldt Park

4.75 out of 5 average rating, 323 reviews

Cozy Garden Studio in West Town, w/ Private Entry.

MiltonRating, 5 stars1 week ago

Place was great. Neighborhood and community was beautiful.

Holiday home in Wicker Park

4.88 out of 5 average rating, 100 reviews

Penthouse. Historic Wicker Park. Walk | Shop | Eat

RachelRating, 5 stars4 days ago

This place was perfect for our needs. Unit matched the pictures. Furniture and bedding were of great quality. Finishes in the kitchen and bath were beautiful. We leveraged all the amenities: parking, dishwasher and laundry. Our teenager loved the room with the bunk beds, and our dog loved having the park right across the street. Would stay again and recommend this rental. Thanks for hosting us!

Apartment in Noble Square

5 out of 5 average rating, 7 reviews

Chicago Citrus Charm 2BR | WestTown

CarlosRating, 5 stars2 weeks ago

Beautiful place to stay some days in Chicago, I recommend it 100%

Apartment in Near North Side

4.92 out of 5 average rating, 37 reviews

Lincoln Park Haven: Balcony, Walk to Whole Foods

HoustonRating, 5 stars1 month ago

We had a great stay at this apartment in Lincoln Park. The view was excellent, and the building amenities were a nice bonus. The location was convenient too--Whole Foods was right across the street, with other shops like REI nearby. It was easy to get downtown and explore other parts of Lincoln Park. We were traveling with a toddler and a newborn, and the host helped by providing a pack 'n play. Communication was clear and timely. Overall, a smooth experience.

4.9 out of 5 average rating, 51 reviews

Pierce Place in Wicker

ChristineRating, 5 stars3 weeks ago

The Pierce house was perfect for our stay while we visited for a college graduation. Quiet location near restaurants, grocery store, etc. Beds were very comfortable. The house is decorated really hip and everything was as described. We rented a car and there was no problem finding parking. Just beware the stairs getting into the house are a bit steep if you have mobility issues like me. However, it was worth every step. Jacqueline very responsive and helpful. We will definitely rent again our next visit!

4.98 out of 5 average rating, 47 reviews

Stylish 2-Bedroom Wicker Park Apartment

NenaRating, 5 stars2 days ago

Very nice apartment in a nice neighborhood. The pictures are true to reality. The bedrooms and bathrooms are small and we had to keep our suitcases in the living room and hallway. There was a decent size closet in each bedroom with hangers and shelves. The beds and beddings were comfortable. The apartment is within short walking distance from many good places to eat.

4.96 out of 5 average rating, 28 reviews

Apartment in West Town

Newly Remodeled in West Town

ShreyaRating, 5 stars1 week ago

Sarah’s place was lovely! We had a wonderful time — it was within walkable distance to main attractions, and the neighborhood itself was safe, nice, and clean.