Vacation rentals in Pilsen, Chicago

Apartment in Lincoln Park

A large dining table made of wood is surrounded by minimalist lighting fixtures. Natural light enters through multiple windows, highlighting the room's mix of exposed brick and modern furnishings. A cozy seating area is visible, featuring a sectional sofa and a television mounted on the wall.

5 out of 5 average rating, 254 reviews

Explore Lincoln Park from a Polished Apartment

JulieRating, 5 stars1 week ago

Beth's place was beautiful, clean, and the location in Lincoln Park was perfect. My husband and I spent 5 days exploring Chicago, and because of the apartment's convenient location, we were easily able to get anywhere we were going via public transportation. The neighborhood itself is charming, and walkable to shows, restaurants, stores, and everything we needed. Communication with Beth was easy, and we appreciated her hospitality, recommendations, and responsiveness. We hope to return someday!

4.8 out of 5 average rating, 160 reviews

A bright and open dining area features a wooden table surrounded by multiple white chairs. Large windows allow natural light to fill the space, highlighting a modern living room setup with a green sofa and a decorative plant.

Condo in Lincoln Park

Massive Old Town Home Steps to Wells St & Beach

SarahRating, 5 stars4 weeks ago

We booked this house for a group of nine women for an annual reunion. It was important for us to each have our own bed, a large variety of bathrooms, a nice size kitchen for cooking, ample seating and room to spread out. This house fit the bill perfectly. We were within walking distance of the lakefront so we were able to spend one afternoon at Lincoln Park zoo and the other afternoon walking around Lincoln Park.

Apartment in West Lake View

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

4.94 out of 5 average rating, 177 reviews

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

DianeRating, 5 starstoday

Sam’s place was beautiful! We felt right at home. The furniture was comfortable and the kitchen had everything we needed. The location was great. We got a free parking spot right outside of the door. Super convenient. We brought our dogs and it was perfect for them. Lots of places to walk and lots of things to do. It was just a short walk to the train. Sam was very easy to get ahold of and was a great host. I definitely recommend and we will be staying here again.

5 out of 5 average rating, 11 reviews

A modern kitchen featuring a large island with seating for six, complemented by sleek cabinetry and stainless steel appliances. Natural light fills the space through a nearby window, and an adjacent dining area is visible, offering a blend of functionality and style.

Home in Avondale

Alluring Avondale Abode

MichaelRating, 5 stars2 weeks ago

Beth’s home was perfect for our group trip, which centered around cooking together for a Passover Seder! The kitchen had great appliances and equipment, with the space for many of us to cook at once. The house had everything we needed and we were all comfortable.

4.95 out of 5 average rating, 104 reviews

A modern kitchen features sleek dark cabinetry and stainless steel appliances. Natural light enters through skylights, highlighting a small dining table with two chairs. The warm wood flooring complements the design, while a light fixture hangs gently from the exposed beam ceiling.

Guesthouse in Oak Park

O'Malley Oasis!

AndreaRating, 5 stars3 months ago

Clean, beautiful space. Has everything needed and the most comfortable seating space to relax. Clear instructions, easy parking. Be aware that there are several stairs to enter as seen in the pictures. They are well maintained with a handrail. This was not an issue at all for us but could be for someone with mobility limitations. Otherwise one of the best places I have stayed in Oak Park. Hope it is available when I come back.

4.96 out of 5 average rating, 280 reviews

The exterior of a three-story residential building is depicted, featuring a wooden porch with steps leading to the front door. Large windows allow natural light to enter, and greenery surrounds the entrance, complementing the light-colored siding and red brick foundation.

Apartment in Irving Park

Spacious 1BR apartment in a central location

GilRating, 5 stars1 month ago

I have stayed in a number of AirBnB‘s throughout the years, this may have been my favorite stay. There is absolutely everything you would need for a comfortable stay. Everything is clean. Alex is a five-star communicator. It is a busy little neighborhood, but the bedroom is toward the back of the apartment. I heard nothing but dead silence at night.

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Popular amenities for Pilsen, Chicago vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Pilsen, Chicago's top sights

National Museum of Mexican Art222 locals recommend

Guaranteed Rate Field120 locals recommend

Chinatown217 locals recommend

Walgreens183 locals recommend

Cermak Fresh Market170 locals recommend

Dusek's Board & Beer155 locals recommend

Apartment rentals in Pilsen, Chicago

4.97 out of 5 average rating, 107 reviews

A modern living space features a dark sofa adorned with colorful cushions. A round coffee table sits in front, accompanied by a small side table with a decorative vase. A large mirror reflects the cozy atmosphere, while a vibrant city skyline artwork adds visual interest to the wall.

Apartment in Avondale

Lovely 2bedroom 1bath Apt and outdoor seating.

DarenRating, 5 stars1 day ago

A very nice and welcoming place to stay!

4.82 out of 5 average rating, 185 reviews

A modern living area features a beige sectional sofa and a round coffee table set on a patterned rug. A large flat-screen TV is mounted on the wall, and a potted plant adds a touch of greenery. Natural light illuminates the space.

Apartment in Chinatown

New apartment

Gary QilieunRating, 5 stars5 months ago

Loved the walkability and great access to transit and chinatown restaurants. amazing stay! thank you!

Apartment in East Rogers Park

The living room features a light grey sectional sofa adorned with colorful throw pillows. A large coffee table sits in the center, surrounded by two mustard-yellow chairs. A modern floor lamp and artistic wall painting add character to the space, complemented by neutral-toned accents.

4.89 out of 5 average rating, 166 reviews

Executive Apartment on Lake Michigan with parking

DebraRating, 5 stars1 month ago

This was a beautiful place with an excellent view of Lake Michigan. Both rooms had comfortable beds and setup with everything you need. Kitchen is well stocked, but we mostly ordered Grub Hub, lol. Loved spending time here and great place to hangout and chat with friends. It is right on the water and we really enjoyed watching the waves crash against the barrier. It is on the 2nd floor, but the stairs are not bad at all. Felt very safe and having the parking space is a great perk. Very commutative and checked in with us to make sure everything was fine. Would definitely stay here again!

4.84 out of 5 average rating, 163 reviews

A cozy living space features a round table with two woven chairs and a small potted plant in the center. A light-colored sofa is placed against the wall, accompanied by a floor lamp on a side table, creating a comfortable atmosphere.

Apartment in Whiting

NEW! |Studio Apartment Whiting IN, United States#2

JoeRating, 5 stars1 month ago

We were in town for a show at the Casino, this place was tremendous. Very easy to find, super close to the Casino and the room was quite nice. Would definitely book again if we find ourselves in that area again 😁

4.98 out of 5 average rating, 212 reviews

A spacious living area is furnished with a dark sectional sofa, accented by decorative pillows. A round coffee table rests on an area rug, while a television is placed on a dark wooden stand. Natural light filters through large windows with sheer curtains.

Apartment in Chicago

Chicago Airbnb Newly Remodeled 2-Unit Apartment!

MarissaRating, 5 stars1 day ago

Brittney’s space was even better than it looked in the photos. this is truly the best airbnb experience i’ve ever had. the apartment was cleaner than any hotel i’ve ever stayed in - I mean it was SPOTLESS. very cute and cozy, and was much bigger than the photos portrayed.

Apartment in Roscoe Village

A bright living room is highlighted by large windows that invite natural light. A comfortable brown leather sofa and a beige loveseat are positioned around a colorful area rug. A wooden coffee table and a wall-mounted TV complement the inviting space.

4.97 out of 5 average rating, 145 reviews

Inviting 2 Bedroom Apartment in Roscoe Village

GaryRating, 5 stars2 weeks ago

We really enjoyed our stay! We really like Roscoe Village and this apartment was perfectly located. Close to shops, coffee and restaurants. The check in process was easy and the apartment was well appointed with everything we needed. Parking was very easy as well. This was a great find for us and we will plan to visit again!

Apartment in Lincoln Park

The living area is characterized by a vintage fireplace and mid-century furniture. A large artwork hangs above the mantel, and a round dining table is partially visible in the adjacent area. Natural light brightens the space through windows draped with sheer curtains.

4.93 out of 5 average rating, 505 reviews

Victorian Home in Old Town

AlexRating, 5 stars5 months ago

I really enjoyed my stay! I loved the art and decor of the space. I am a solo traveler and I felt safe being here. There are written instructions on the door and in the home that explain almost everything I needed. I felt safe in the neighborhood! I would get back late and felt safe doing so. There are multiple stores within walking distance so it was easy to grab food or any items I may have needed. I didn't have a car and found it very easy to get to everywhere I wanted to go. Shampoo/Conditioner/Body Wash was a pleasant surprise to have! Along with the teas and coffee items. The space was a great size and I had everything I needed. It was easy to come and go and check in was very easy. I would stay here again, Lynn was super responsive, helpful, and kind! The bedroom area doesn't get much light, but it wasn't an issue for me. Bed was comfy, home was beautiful, and I loved my stay. Thank you so much Lynn!

4.91 out of 5 average rating, 103 reviews

A cozy living area features a green sectional sofa adorned with yellow accent pillows. A wooden coffee table sits in the center, complemented by a light grey armchair. Natural light streams in through a skylight, highlighting the rich brown flooring.

Apartment in Avondale

Avondale Cozy 1 Bedroom Attic Apartment 4th FL

CatherineRating, 5 stars3 weeks ago

Great place, beautiful attic and great amenities from host!

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Other great vacation rentals in Pilsen, Chicago

4.92 out of 5 average rating, 39 reviews

Home in West Lawn

Family Friendly Duplex/9 min from MDW/Free Parking

JoannaRating, 5 stars2 weeks ago

Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗

4.87 out of 5 average rating, 23 reviews

The open living area is highlighted by a neutral color palette and modern furnishings. A coffee table sits in the center, and a flat-screen TV is mounted on the wall. Natural light is filtered through large windows, enhancing the spacious feel of the room.

Home in Elmhurst

Enamored in Elmhurst

EmilyRating, 5 stars2 days ago

We had a great stay. The house was perfect for our group - 4 adults and 1 baby. Very clean, with great facilities. The wireless chargers were so helpful as we were international visitors. Also, the provision of tooth brushes, mouthwash and razors in the bathroom was a great bonus. Plenty of towels, comfortable beds and lovely location near the Prairie path made it a wonderful stay.

4.85 out of 5 average rating, 130 reviews

A panoramic view of the Chicago skyline is presented, featuring iconic buildings illuminated against a dramatic night sky. The Willis Tower stands tall, with its lights creating a vibrant display amidst the clouds. The landscape showcases a blend of urban architecture bathed in colorful hues.

Apartment in West Town

Condo with private terrace, free WIFI and parking

OlesyaRating, 5 stars2 weeks ago

The place looked much better than on the pictures! It has rooftop patio, spacious, clean, with a unique interior design (vintage). It had plenty of towels, dishes, comforters, so we will definitely come back there when we are in Chicago.

4.86 out of 5 average rating, 42 reviews

A cozy living area is presented, featuring a stone fireplace as a focal point. Two armchairs are positioned around a coffee table, with decor additions providing a touch of greenery. Natural light enters through nearby windows, illuminating the light-colored walls and hardwood floors.

Apartment in Albany Park

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars2 months ago

Wonderful stay as always, thank you so much!

Apartment in Jefferson Park

A modern kitchen is equipped with sleek stainless steel appliances, including a microwave and dishwasher. Light countertops complement dark cabinetry, while a small countertop with two barstools provides a casual dining option. Natural light filters in through a window near the door.

4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars1 month ago

Peaceful, felt like home, very spacious and comfortable

Condo in East Rogers Park

The exterior of a three-story Art Deco building is showcased, featuring a light-colored brick facade and large, symmetrical windows. A wrought iron fence surrounds the property, with well-maintained greenery enhancing the entrance. The sky above offers a clear blue backdrop.

4.79 out of 5 average rating, 29 reviews

Spacious condo with open floor plan and fireplace

TatianaRating, 5 stars4 months ago

This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.

4.79 out of 5 average rating, 179 reviews

A green, two-story house is framed by large trees in a quiet neighborhood. The front features a central door with a decorative window and light-colored trim. Leaves cover the ground, indicating the autumn season. The pathway leading to the entrance is bordered by grass.

Home in Cicero

Spacious whole apt near shopping and city

AnthonyRating, 5 stars1 week ago

spot very spot on for the price , neighborhood and parking was nice and everything was calm and clean. recommend very much and definitely will come again