
House vacation rentals in Pilsen
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Top-rated house rentals in Pilsen
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Spacious Five Bedroom Home in Trendy Chicago Neighborhood
Unwind on the private rooftop deck, soak in the luxurious jacuzzi tub or take a relaxing steam shower after you host a dinner party in your own spacious dining room. Then watch a movie in the entertainment center with popcorn machine and 75 inch TV. Bedrooms are as follows: Master - king 2nd - twin and crib 3rd- queen 4th - twin over full bunk 5th - king and twin over twin bunk We also have a large, U shaped, 40 inch deep Cloud sectional from RH that can sleep 2-3 and 2 air mattresses. Stunning newly renovated home in a fantastic Wicker Park Location! Wicker Park is the Brooklyn of Chicago with tons of unique shops, restaurants full of character and innovative bars. The entire home is yours, giving you rarely found complete privacy in the middle of the city for you, your family, friends and colleagues to enjoy! Expertly designed with gourmet kitchen and multiple living rooms, your party will have plenty of room to spread out during your stay in the Windy City. Utilizing the finest materials & craftsmanship available, some of the premium features include: hardwood flooring on entire 1st and 2nd levels, 10' ceilings, beautiful moldings, sensational gourmet kitchen with large center island, premium stainless appliances and quartz counters, extra-large bedrooms including luxurious master suite with lavish marble baths, steam shower and expansive walk-in closet. Five full bedrooms and 4 bathrooms. The master bedroom has a King bed and very large ensuite bathroom. Bedroom 2 has a twin bed and a crib (upon request), bedroom 3 has a queen bed and a daybed. Bedrooms 2 and 3 share a hall bath. Bedroom 4 has bunk beds and bedroom 5 has a king bed and a daybed. Bedrooms 4 and 5 share a bathroom. The basement has a large entertainment area with a wine fridge, popcorn machine and 75 inch TV. **For those with infants and toddlers, in addition to a crib, we also have a SNOO bassinet and a Bugaboo cameleon stroller for your use. **If you would like to use any of these, please specify in your booking so that we can have them out and available to you. Otherwise, we keep them out of the way for guests who are not needing them. If you need parking please let me know in advance ** We have keyless entry for super easy check in. I am always available by phone, texting is best, but we want you to have the most convenience possible. That’s why we have keyless entry for seamless check in. No hassle for late arrivals, etc. Simply type in the code provided after confirmation and you’re all set! The neighborhood is the most buzzed about in Chicago, with trendy restaurants, shops, and bars within an easy walk, not to mention the beautiful park. Blue line is only a few blocks, which gives direct access to O'Hare International Airport. Uber and Lyft are always minutes away, and a Divvy bike station is right around the block. Chicago is a great city to explore. We are in the living breathing heart where locals reside so you’ll get the best the city has to offer!

Cool Quiet Coach House, Private Access + Patio
Retreat to the brick patio of this lovingly renovated home after a long day traversing the neighborhood. The interior is an expression of creativity, greyscale walls, rustic accents, and a varied selection of art and wall hangings tie in the decor. Split Level Floor plan. 1st floor = Living, Eat in Kitchen, bedroom 1 and bathroom. 2nd Floor = 2nd bedroom , bath and an additional sleeping area and desk area. Also features a gorgeous shared yard. The entire coach house is yours!! The coach house is set back behind a 2 unit building and the yard is shared between both. We are available via text or airbnb messaging and try to respond quickly. Please reach out anytime if you need anything at all. Extra supplies, neighborhood recommendations or tips in the neighborhood. The home is located on the border of Wicker Park and Bucktown which is Chicago's original hub of cool. It is a vibrant enclave of culture and commerce, explore vintage finds, record stores, and plenty of indie shopping in this trendy part of town The 24 hour Blue Line EL train is just a 5 minute walk. Door to Door it's only 25 minutes to Millennium park. (5 min walk to the blue line, 10 min ride on the train, 10 minute walk to the Park). The neighborhood is pedestrian and bike friendly , the 606 trail is just a few blocks away also.

Flat in Lincoln Park 2-Flat Central to Everything
Historic, newly renovated flat in the heart of Lincoln Park, with garage! A block from the famous Blues club "Kingston Mines". Close to great bars and restaurants, including Alinea, the only restaurant in Chicago awarded 3 Michelin Stars. A mile to Lincoln Park Zoo, less than 1-1/2 miles to the lake. Beautiful yard (shared with lower unit) has gas grill, patio, deck, and a garage space. Enjoy the Lincoln Park area in this unique home that offers everything you need for your holiday in Chicago.

Chicago's Bridgeport Huge 4 Story w/Garage Parking
Large and beautiful 4 story single-family home centrally located in the trendy Bridgeport community of Chicago. The house is 5 minutes from McCormick Place, 3 miles away from Magnificant Mile shopping on Michigan Ave. 2 blocks from the Bridgeport Art Center, and 5 minutes from Soldier Field! 6 blocks to catch a White Sox game! Close to beaches and Lake Shore Drive, this spacious and welcoming home will serve all your vacation needs. 5 minutes from Chinatown, Greektown, Little Italy, and Pilsen.

Charming 3-BED in Lincoln Park/ Old Town & Parking
Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.

RetroModern Bungalow | free parking | pet friendly
Experience the city in style at Retro Modern Bungalow, the perfect pad for up to four friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location—just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Cozy garden apartment historic Jackson Bvld.
Just a short walk to the United Center our cozy 1 bdrm garden apt is located on Historic Jackson Blvd's tree lined st. Stop back & warm up by the fireplace before heading out to near by shopping & restaurants. Less than an hour from Midway or O'Hare. Walking distance to Randolph St. Restaurant Row, Little Italy, Greek Town, Union Pk, Fulton Warehouse Dist, Rush Hospital and UIC. A quick train/bus to The Loop, Theater Dist, Mag Mile, Wicker Pk. Free, convenient street pkg.

Modern Getaway w/ Hot Tub, Lrg Yard, Parking
1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard. The property has a parking slab in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! Please reach out with any questions you may have before booking. NO CHORES! Hot tub 5-6 Person Spa

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).

Whole apartment! 2 Bed/2 bath steps from Wrigley!!
Newly rehabbed urban nest among the tree-lined streets of beautiful East Lakeview. Literally 60 seconds to Wrigley Field, close to bars, restaurants, El train/busses, and lakefront. You’ll have loads of space in this 2 bed, 2 bath, plus office and large laundry room with FREE full size W/D. Free parking passes! Owner lives near by and is happy to help with anything you need to make your trip the best it can be. Flexible check in/out times upon request.

Peaceful Modern Full House in Trendy Bridgeport
Kick back & relax in your home away from home in our modern & peaceful space in the heart of the Bridgeport neighborhood. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located on popular Morgan Street, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

Paradise on the Park
Located in Chicago’s hot West Town neighborhood. This is a one bedroom one bath unit in a quiet nook directly on Smith Park. Access to the park across the street with pickle ball courts, tennis courts, baseball field, and picnic areas. Situated close to Wicker Park and Bucktown. Plenty of FREE street parking directly across the street on the park side of the street.
Popular amenities for Pilsen house rentals
House rentals with a pool

Chic Fulton Market Oasis + Curated Comfort & Style

Luxury fenced in modern ranch

Chicago Oasis

Bedford Palace

PRIME Designer Retreat w Patio | Fire Pit |Parking

Rosemont 4BD2BA house with Pool

Lucky #7 w/ Gym
Weekly house rentals

The Architectural Haven

House Bucktown /wickerPark.

CasaNova Modern City Living

Floresitas Oasis, your home in Chicago

Old Chicago - a Historic and Pet Friendly Retreat

Chicago Row House Garden Apartmt

Calm and Spacious: A Modern Sanctuary

Large Home | Free Parking | Near Downtown
Private house rentals

Chicago Home (1st floor) by Midway near Downtown

The Modern Muse of Chicago! Close to everything!

Chic Urban Home Near Chinatown/Downtown /McCormick

Cozy Home in Brookfield

3bd Home with Luxurious Kitchen

jane's house - a boutique flat in west town -2b/1b

Oak Park - Wine House!

2 BR • CTA Blue Line to Chicago • Free Parking
Quick stats about house rentals in Pilsen

Total vacation rentals
Explore 40 vacation rentals in Pilsen

Nightly prices starting at
Pilsen vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

Verified guest reviews
Over 940 verified reviews to help you choose

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
40 of Pilsen vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Pilsen rentals
Destinations to explore
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- 875 North Michigan Avenue
- Soldier Field
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Brookfield Zoo
- Illinois Beach State Park
- Willis Tower
- University of Chicago
- Washington Park Zoo




