Vacation rentals in Logan Square

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Top-rated vacation rentals in Logan Square

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Top guest favorite
Apartment in Forest Park
4.98 out of 5 average rating, 400 reviews

Walk to Oak Park from Our Sunny Turn of the Century Apt

Soak up the vintage charm of this apartment dating back to 1908. This newly remodeled space is an elegant retreat, featuring 10-foot ceilings, local art treasures, and plush linens. A relaxing outdoor lounge area awaits after a busy day exploring. Pets are welcome on a case by case basis (contact host). The space is a charming two bedroom, one bathroom first-floor unit in a two unit historic home built in 1908. The apartment combines historic details with modern conveniences such as central heat and air, a dishwasher and washing machine and dryer access. The Monroe House is a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 25 minute train ride away. The condo includes additional amenities such as: •Smart TV for watching any account may you have (Netflix, Hulu etc...) •Central Air conditioning •Front and back porches for your enjoyment •Washer and dryer on site Just to the east lies historic Oak Park, and an array of attractions such as: •Brookfield Zoo •Chicago Architecture Foundation •Ernest Hemmingway Museum and Birthplace •Frank Lloyd Wright Home and Studio •Frank Llyod Wright’s Unity Temple •Oak Park Conservatory After taking in the local attractions, Chicago is only a train ride away, and it offers such noteworthy experiences as: •Shedd Aquarium •Architecture River Cruise •Skydeck Chicago •Navy Pier •The Field Museum •John Hancock Observatory •Adler Planetarium •Art Institute of Chicago •The Museum of Science and Industry You will have access to the entire unit and the basement so you can use the washing machine and dryer. We also have a back patio with a chiminea, patio table that seats 6, and a grill/smoker. You are welcome to use the backyard at anytime during your stay. We live in the top unit and are as available as you need. That being said, we very much respect your privacy and will not be checking in with you in person unless you request it. It is located in the Madison district, with acclaimed restaurants, pubs, and unique boutiques. Downtown Chicago is a 25-minute train ride away. The local brewery across the street offers delicious beers and creative meals for the whole family. We have a parking pad located behind our building. You can fit two cars on your side of the parking pad if they are parked in tandem. Some street parking is also available. We are located .4 miles from the CTA Blue Line train - Forest Park Stop. It is about a 6 - 10 minute walk from the flat. You can also take an Uber/Lyft into the city. It is about a 15 - 25 minute ride and it costs between $15 and $25. We are located about one mile from the Metra Station (Union Pacific West) and CTA Green Line - Oak Park Stop. Third bed is a queen sleeper sofa. We provide sheets and blankets for the sleeper sofa. You can smoke in the backyard. An ashtray is provided.

Top guest favorite
Apartment in Evanston
4.99 out of 5 average rating, 107 reviews

Evanston 2BR 2Bth 1 Blk to Beach

With its older charm, modern comforts, and unbeatable proximity to the beach, this 2-bedroom, 2-bath unit offers an ideal getaway. Only 1 block from beautiful Lake Michigan and South Blvd Beach, you will love our spacious, sunny apt. Whether you're staying for a short visit or a lengthy one, you'll feel the comfort of home on a tree-lined street. The unit has hardwood floors throughout, comfortable bedrooms, a fully stocked kitchen, dining room, and a sunroom looking out on the backyard patio.

Top guest favorite
Guesthouse in Oak Park
4.97 out of 5 average rating, 118 reviews

Oak Park cozy carriage house-lovely, walkable area

Our comfortable, stylish retreat has everything you need to relax and recharge. Whether you are visiting to explore all that beautiful Oak Park and downtown Chicago offer or desire a peaceful space to work. -> Quiet, walkable street near popular cafes, restaurants, taverns, parks, historic homes -> Steps from the "L" Blue Line Oak Park station -> Stocked w/ snacks + gourmet coffee/tea set-up (grinder, AeroPress, and Keurig) -> Onsite off-street parking -> A/C + heat -> garden sitting area

Guest favorite
The historic manor house features a rich red brick facade adorned with lush green ivy. The spacious porch extends from the building, complemented by well-maintained gardens that enhance the inviting exterior. Large windows provide ample natural light, creating an open and airy ambiance.
Guesthouse in Evanston
4.93 out of 5 average rating, 133 reviews

Historic Coach House in Evanston Near Beach & Town

Stay in the Coach House of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire coach house which is renovated and includes a large bedroom with king bed and desk, a sun-filled living room/dining room, a full bath with claw-foot soaking tub and shower and a kitchen with amenities. The space can be equipped with an air mattress for an extra guest. Also available is a 3rd floor guest suite in the main house.

Top guest favorite
A light-filled living room features a comfortable beige sofa with an accent pillow and a light throw. Adjacent windows allow natural light to stream in, highlighting the wooden flooring and decorative area rug. A small side table holds a lamp, contributing to the calm atmosphere.
Apartment in Evanston
4.97 out of 5 average rating, 539 reviews

Charming, Sunny Apartment with Backyard Garden

House of the Blue Doors Enjoy staying with us in this spacious 1st floor flat. Furnished by the resident designer in tasteful neutrals, original curated artwork, one of a kind furniture and accent pieces. Sip morning coffee or a glass of wine in the sunlit kitchen or front porch, fire up the backyard grill for a barbecue. Soak in the award winning Chicago ceramic artist designed and made floor in the bathroom. Close to Northwestern, Chicago, Lake Michigan, everything Evanston offers.

Top guest favorite
The exterior features a charming two-story home with a welcoming front porch. A set of stairs leads to the entrance, surrounded by well-maintained greenery and blooming flowers. Sunlight filters through the trees, creating a warm and inviting atmosphere.
Guest suite in Evanston
4.98 out of 5 average rating, 287 reviews

A guest suite centrally located, but so quiet

IF... you want to race into the city to see a play, go for a jog along the lake, have a quick coffee with a friend or enjoy a fine restaurant to celebrate a special occasion, it's all here in the lovely lakeside town of EVANSTON, IL. You can enjoy it all while living in my private guest suite w/kitchenette, private bath, private entry, shared laundry area and......., if you need it, garage parking, too! Enjoy my garden on warm summer days; in winter, you will love the heated floor!

Guest favorite
A cozy living space features a light-colored armchair next to a small round table. A wall-mounted TV is positioned above a classic white fireplace, where a small potted plant is placed. Natural light enters through decorative stained glass windows.
Apartment in Oak Park
4.88 out of 5 average rating, 450 reviews

Chicago-Style, Vintage, Cable & NFL PASS 42-1

→ Introducing our newly renovated and furnished apartment unit nestled in the charming Oak Park Art District. Richly characteristic brick building, Chicago style, situated in a safe and quiet neighborhood. ★ Property Features: • One block away: Oak Park Art District • Vintage Chicago style brick building • Safe, quiet neighborhood • Newly renovated and furnished • Smart TV with Cable • Free Laundry Room • Free Parking for short stays, long stays limit spots please confirm.

Superhost
Condo in Oak Park
4.84 out of 5 average rating, 104 reviews

Lovely condo in the heart of Downtown Oak Park!

The whole group will enjoy easy access to everything from this centrally located place. 2 bedrooms, 2 baths, lots of living space. Open concept kitchen, living, dining, and extra space for work/play space. In-unit laundry. Great outdoor deck, free parking all in the heart of downtown Oak Park with restaurants, theater, street fests, parks, green line/metra for easy access to Chicago. Quiet unit with its own entrance and no shared walls. You will love it here!

Top guest favorite
Apartment in Evanston
4.97 out of 5 average rating, 215 reviews

Stunning, Sunny Flat with Beautiful Backyard

Home away from home in a wonderful and walkable Evanston neighborhood, convenient to downtown, Lake Michigan, Northwestern and more. Treat yourself and your family to this wonderful two-bedroom, masterfully remodeled flat, with all the conveniences and comfort. Off street private parking. Recent updates: New king size bed, 65-inch HD TV, washer & dryer, and more. We follow EPA/CDC protocol and prepare for your stay with intensive cleaning and disinfecting.

Top guest favorite
A cozy living area showcases a brown leather sofa adorned with decorative cushions. A round glass coffee table rests on a patterned rug, complementing the hardwood flooring. Framed artwork decorates the wall, while natural light enters through nearby windows.
Home in Logan Square
4.98 out of 5 average rating, 132 reviews

The Hamlin | Logan Square Home 4BR/2BA w Parking!

✨ Your Chicago Stay, Elevated. 🏡 Welcome to The Hamlin House in Logan Square This design-forward home features 4 bedrooms 🛏️, 2 full bathrooms 🚿, and included two-car garage parking 🚗🚗 — perfect for family trips or group getaways. ⸻ 🌿 Logan Square You’re in Logan Square, known for its amazing food 🍽️, local art 🎨, historic boulevards 🏛️, and easy access to downtown 🌆 — all without downtown hotel pricing.

Top guest favorite
A bright living area features a round chandelier overhead, with plush seating in deep green. Large windows invite natural light, framed by elegant curtains. A coffee table sits center stage, adorned with a decorative tray and a vase of yellow flowers, complemented by a soft area rug beneath.
Apartment in Oak Park
4.98 out of 5 average rating, 370 reviews

Bright & Spacious Victorian-FREE PKG walk to train

This historic Queen Anne home built in 1889 is in the heart of Oak Park. Walk to all tourist attractions, public transportation that takes you directly to downtown Chicago, great restaurants, boutiques and grocery stores. It’s the perfect base for exploring Oak Park and Chicago. We kindly ask that you read our full listing description and our house rules prior to booking.

Top guest favorite
A cozy living area features a light-colored sofa and a dark armchair, arranged around a wooden coffee table. A textured area rug lies beneath, and soft light is provided by a floor lamp. Large, partially draped windows allow natural light to enter.
Guesthouse in Evanston
4.92 out of 5 average rating, 139 reviews

Cozy Guesthouse near NU - next to Lee Street Beach

Welcome to our cozy and comfortable guesthouse nestled on a quiet and beautiful neighborhood in Southeast Evanston. We are 2 blocks from Lee street beach and 10 minutes walking distance to the Main Street El train (purple line) and Metra stop. We are a 10 minute walk to downtown Evanston and Northwestern University. We are 10 miles from downtown Chicago.

Popular amenities for Logan Square vacation rentals

Quick stats about vacation rentals in Logan Square

  • Total vacation rentals

    Explore 460 vacation rentals in Logan Square

  • Nightly prices starting at

    Logan Square vacation rentals start at €9 per night before taxes and fees

  • Verified guest reviews

    Over 39,190 verified reviews to help you choose

  • Family-friendly vacation rentals

    290 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 150 rentals that welcome pets

  • Rentals with dedicated workspaces

    330 properties have a dedicated workspace

  • Wi-Fi availability

    450 of Logan Square vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Logan Square rentals

  • 4.8 Average rating

    Logan Square stays are highly rated by guests—averaging 4.8 out of 5!

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