Vacation rentals in Pulaski Park, Chicago

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Top-rated vacation rentals in Pulaski Park, Chicago

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Superhost

A spacious living area is illuminated by natural light from large sliding doors that open to a tree-lined street view. A plush area rug covers the hardwood floor, while a sectional sofa and a wooden coffee table create a comfortable gathering space. A ceiling fan enhances airflow.

Apartment in West Town

4.9 out of 5 average rating, 283 reviews

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.

Top guest favorite

A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.

Apartment in Lincoln Park

5 out of 5 average rating, 260 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Guest favorite

Guest suite in West Town

4.96 out of 5 average rating, 341 reviews

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

Top guest favorite

A cozy seating area is highlighted by a light-colored chair with an accent cushion and a wooden side table. A tall lamp stands beside the chair, illuminating the space, while a green plant adds a natural touch. Soft light filters through a window with a view of leafy greenery.

Apartment in Wicker Park

5 out of 5 average rating, 117 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

Superhost

A spacious wooden rooftop deck is presented, featuring a built-in bench along the railing. The city skyline is visible in the background, showcasing various buildings under a partly cloudy sky. The deck offers ample space for outdoor seating and relaxation.

Apartment in Wicker Park

4.78 out of 5 average rating, 282 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! The apartment comes complete with a large living space, including a twin day bed which can be pulled out and converted into a king size bed. The kitchenette has a fridge & microwave. There is A/C, fast 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!

Top guest favorite

Condo in Wicker Park

4.96 out of 5 average rating, 106 reviews

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Top guest favorite

A quaint outdoor seating area is surrounded by greenery, featuring a round metal table and four matching chairs. Bright red flowers are placed in a decorative pot at the table's center. A stone pathway guides toward the area, complemented by a rustic wooden fence and sculptures peeking through the foliage.

Apartment in West Town

4.95 out of 5 average rating, 430 reviews

A Vintage Pink House in the Heart of Chicago

Located in a quirky, Victorian era, pink house on a residential street in the East Village neighborhood, this unit is a charming piece of Old Chicago. This 2nd story, apartment features an eat in kitchen, a double and a single bedroom, and a front room that oozes Chicago history. Perfect for a quick weekend getaway or an extended stay. A Walk Score of 97 means you won't need a car to experience the city. Easy access to Division Blue Line, nightlife, shopping & adventure.

Guest favorite

A spacious living area is highlighted by a modern leather sofa facing a mounted television. Natural light pours in through double glass doors, which lead to an outdoor space. A minimalist decor includes a stylish mirror and a potted plant, enhancing the inviting environment.

Home in Wicker Park

4.97 out of 5 average rating, 243 reviews

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).

Top guest favorite

A panoramic view of the Chicago skyline is captured at sunset, showcasing a blend of urban architecture. Streets are filled with vehicles, and neighborhoods are highlighted by warm hues reflecting off building surfaces. Dramatic clouds create depth in the evening sky, enhancing the cityscape.

Apartment in Logan Square

4.96 out of 5 average rating, 124 reviews

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.

Top guest favorite

A textured stone wall is featured, highlighting a red lettered sign marked 'F'. A sleek mail slot is positioned below the sign, and a metal pipe runs vertically alongside the wall, adding to the industrial aesthetic of the building.

Apartment in West Town

4.97 out of 5 average rating, 151 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!

Superhost

A modern living area features a light gray sectional sofa, complemented by a low coffee table and a stylish area rug with dark and light stripes. Exposed brick walls and contemporary artwork enhance the space, while a dining area is visible in the background.

Loft in Wicker Park

4.93 out of 5 average rating, 204 reviews

Trendy Wicker Park Loft with Parking

Located in trendy Wicker Park, our modern Chicago loft boasts open-plan living, exposed brickwork and plenty of room to accommodate larger groups. Walk down popular North Ave, Milwaukee Ave and Division St. to explore the many shopping, dining, and nightlife options We are centrally located, close to the Blue Line (airport and downtown access) and a block away from the Kennedy (I90/94 expressway).

Superhost

A vintage-style record player is displayed on a wooden cabinet, featuring a rich wood finish. The record player's lid is opened, revealing the turntable. A decorative glass piece sits nearby, contributing to the charming ambiance of the space.

Apartment in Wicker Park

4.82 out of 5 average rating, 211 reviews

Ina's Beachwood Inn In the Heart of Wicker Park

Located on the second floor of Ina Mae Tavern & Packaged Goods, one of Chicago's best new restaurants, the Beachwood Inn has a private balcony overlooking the entire restaurant's bustling action so guests will never miss out on the happenings - from live music to brunch and dinner. The space is perfect for travelers who want to immerse themselves in a true local experience.