Holiday rentals in Pulaski Park, Chicago

5 out of 5 average rating, 264 reviews

Flat in Lincoln Park

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.

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.

Superhost

4.78 out of 5 average rating, 284 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!

4.94 out of 5 average rating, 327 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, 109 reviews

Apartment in Wicker Park

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.

4.92 out of 5 average rating, 360 reviews

Flat in West Town

Spacious & private! Free parking! Great location!

Tough to beat this location (River West), accessible to everything via public transportation, great spots walkable from your door & free street parking nearby! Spacious open floor plan provides you a quiet escape from the excitement of the city! It's very comfortable & well designed for a perfect visit! Steps to local dining, great coffee, brewery, cocktails & so much more. Get to almost all popular spots in Chicago in 5-10 minutes! 3 minute walk to the Chicago blue line, 56 & 66 bus lines.

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.

4.97 out of 5 average rating, 247 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

Flat in Logan Square

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.

Superhost

Apartment in West Town

4.81 out of 5 average rating, 155 reviews

Cabin 207 at 747 Lofts

This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away!

4.95 out of 5 average rating, 107 reviews

Apartment 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 Pulaski Park, Chicago

4.96 out of 5 average rating, 83 reviews

Flat in West Town

Wicker Park Walk-Up Condo

KameshRating, 5 stars2 weeks ago

My family and I enjoyed Randy's place; it was clean and well maintained. The location is a short walk to a street with multiple restaurants, shops, and bars. I felt safe walking around, even at night. There is a subway stop a short walk from the property also. A couple of other nice items to note: 1. The property has a washer and dryer with detergent supplied. This came in handy. 2. There were two premium streaming services provided. HBO and Cinemax I think.

4.96 out of 5 average rating, 171 reviews

Wicker Park Top-Floor Private Balcony Views

YvonneRating, 5 stars2 weeks ago

This was a great place to stay. It was clean and had everything you needed. If we didn’t have something we needed I’m positive Sara would have had it here. The place was quaint, had character and so comfortable. The deck was awesome with a view of the city. The neighborhood was quiet and had lots to explore. It was easy going into the city by uber and the line. Sara also graciously let us check out at 5:00 because we had a late flight going back home. We would definitely stay here again, highly recommended.

4.84 out of 5 average rating, 526 reviews

Private room in Chicago

Egyptian Room - Free Parking, 1 block to CTA

TrentRating, 5 stars2 weeks ago

Former Chicago resident here—Ryan’s place was so nice I stayed here twice and had great experiences both times as a solo traveler. The neighborhood is peaceful, close to the Green line CTA stop, and the house is an amazing place-clean, multiple bathrooms, nice kitchen, terrific value and often presents opportunities to chat with other guests. My room and bed were quite comfortable. The mini fridge came in handy and I really appreciated having coffee available for mornings when I didn’t have time to stop by Dark Matter, Intelligentsia, or The Worm Hole. I look forward to staying again next year!

Private room in West Town

4.89 out of 5 average rating, 113 reviews

Picturesque Room in West Town!!

LaraRating, 5 stars2 weeks ago

It was a pleasure staying at Shaun’s place. He is friendly, quick to answer questions and make recommendations. We had a great time in Chicago and Shaun and his place added to the enjoyment. Thanks Shaun!

Flat in West Loop

4.72 out of 5 average rating, 326 reviews

Sonder Market Hall | King Studio Apartment

JadenRating, 5 stars2 weeks ago

I had a pretty awesome stay. Will book again the next time I come to Chicago!

Private room in West Town

4.93 out of 5 average rating, 164 reviews

Hattie’s House

ElenaRating, 5 stars2 weeks ago

Marcos was incredibly friendly and accommodating! The space was beautifully decorated, and I enjoyed the location perfectly. Very close to transit, plus Marcos recommended great places nearby to eat. A wonderful airbnb experience for solo travelers.