Guesthouse vacation rentals in Chicago

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Top-rated guesthouse rentals in Chicago

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Top guest favorite

The exterior of the carriage house is showcased, featuring red brick walls and large arched windows. A set of concrete steps leads to an entrance framed by greenery, enhancing the welcoming appearance of the building.

Guesthouse in Little Italy

4.99 out of 5 average rating, 845 reviews

Polk Street Coach House Apartment, Little Italy/Medical Dist

Cook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs. Welcome to Polk Street Guest House: a well-appointed, completely private, 2-bedroom carriage house in Little Italy near the Medical District. Decorated with mid-century antiques and paintings, our 2nd floor coach house apartment is perfect for guests looking for a home-away-from-home. It has a fully-equipped kitchen, teak furnishings, comfortable queen size beds, and a private entrance accessible though a side gate from the street. For folks with kids, please note there is no child gate near the top of the stairs. Enjoy quiet parks and have easy access to all of Chicago. Major hospitals at Rush, University of Illinois, Hines, VA and Stroger are within 3 to 6 blocks. Chicago's elevated pink line train is 2 blocks away; the Blue line is 3 blocks. Take a quick cab ride to “the loop" downtown for $10, or take a Divvy bike. Chicago's famed Little Italy restaurants on Taylor Street are a block South. Free street parking with 24-hour zoned pass. Your hosts: Ken & Curt Want privacy? You have privacy! Use an entry code to access the coach house through the side gate to the left of our main house. Your private entrance, which also has keypad entry, is on the left side of the vine-covered brick building in back. The main living area is upstairs. There will be a 24-hour zoned parking pass waiting for you on a shelf as you enter the Coach with instructions on how to fill out the parking pass. We regret that the Coach House is not ADA/wheelchair accessible. For those arriving early than check-in, or who are staying later than check-out, we have an area beneath the coach house where you may leave your luggage. Just ask. Our space is your space. The coach house is entirely separate from our main house where we live. The coach house has a separate entrance and full amenities. You’re welcome to use the seating area in the courtyard, and the Weber grill. We're happy to provide any tips about the city, or to help show you how to use anything in the apartment. Just call our cell phones (they are listed in the apartment), or step across the yard and say hello. Three blocks to the Medical District and major hospitals, walk from this tree-lined Little Italy neighborhood to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Indian cuisine on Taylor Street. Stroll in Garibaldi Park on the doorstep, with Arrigo Park a block away. We are conveniently located for transit, bike, car and Uber. Public Transportation: -Pink Line, Polk Station, CTA: 3 blocks west of us, this rail line gets you downtown in 10 minutes (plan 30 minutes total time with walking for most destinations) and is useful for most site-seeing. -Blue Line, Racine Station, CTA: 4 blocks east or west of us, this rail line gets you to O'Hare airport in less than an hour, or downtown in about 10 minutes (it's a bit longer walk to the Blue Line than to the Pink Line) . -#157 Bus (Streeterville): This super convenient bus 1 block south of us on Taylor Street runs during the daytime only and takes you to the Magnificent Mile for upscale shopping on North Michigan Avenue in 25 minutes. -#12 Bus (Roosevelt): This is about 3-4 blocks south of us, runs east-west, and takes you to the Soldier Field stadium and the Roosevelt Road shopping area with Whole Foods, Nordstrom Rack, Best Buy, Core Power Yoga, and much more. Bicycle: You bike? We bike. There is a DIVVY bike share station a block east in Arrigo Park. Get at DIVVY bike-share 24-hour pass with unlimited half-hour rides. Switch out bikes for longer distances. If you have your own bike, you can park it safely on the ground floor of your coach house apartment. It takes 15 to 20 minutes to bike to most downtown locations. Car: Our home is 3 blocks south of I-290 (the Eisenhower), and near I-55 (the Stevenson), I-90 and I-94 (the Dan Ryan and Kennedy). Parking: We provide parking passes for free zoned street parking available on a small shelf as you enter the Coach House along with instructions. Please be very careful about filling out the pass, as City workers seem motivated to issue tickets if the pass is not filled out correctly. We travel a lot and know what it's like to be away from home. That's why we've furnished the apartment with appealing furniture, comfortable beds, plenty of towels (and more towels), soaps, shampoos, and a kitchen outfitted with all the basics plus a few more: Kitchen Aid food processor, toaster, microwave, baking and cooking tools, Calphalon pots & pans. Please note there is no dishwasher. Enjoy complimentary Nespresso coffee, Bigelow teas, bottle water, and snacks. Three blocks to the Medical District. Walk the tree-lined streets of the Little Italy to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Asian cuisine on Taylor Street. Stroll in Garibaldi Park steps away, or Arrigo Park a block away.

Top guest favorite

A cozy living area showcases large windows framed in light curtains, allowing natural light to fill the space. A comfortable sofa and eclectic furnishings provide a welcoming atmosphere. A coffee table sits centrally on a decorative rug, with a television positioned nearby.

Guesthouse in Edgewater

4.98 out of 5 average rating, 260 reviews

Edgewater Glen Suite in Historical Home

Step into a soothing space in this inviting guest apartment. The space features an open-concept living area and kitchen, a repointed brick masonry wall, contrasting dark surfaces and stark whites, bright wood flooring, and eclectic furnishings. Conveniently located near public transportation, beautiful beaches, boutique shops of edgewater/ Andersonville, great restaurants and Loyola University! Enjoy the elements of a luxury hotel but the feel of a home away from home. The entire suite is all to yourself. It feels like a single family home since you have no one above or below you. We have a lovely front porch with chairs to sit outside and watch the world go by as well as a nice front yard which you are welcome to bring chairs down to and enjoy! We are likely to run into each other as we enter and exit our house but besides that we can be as available as you need! We are right next door so if there are any needs we are easy to reach by phone, text or a quick knock on the door. We do have two friendly golden retrievers that frequent the front yard. Please reach out in advance if you have any allergies/issues with dogs. The neighborhood is lively, safe, family-friendly, and beautiful. People around here take great pride in their homes with beautiful landscaping all over. It is a diverse area and a great place to explore on foot. The easiest way to get here from the airport is uber/rideshare/taxi. It is usually about 35-45 minute by car. However you could also take the CTA blue line downtown and catch a red line to get up to our home. For reference it is 35 minute by train and 15 minute by car from Michigan Avenue/Water Tower place. If you chose to drive here/have a car there is a lot of parking in the area on the street. We are located .2 miles (4 minute walk) from the Granville train (red line), 15 minutes to two beautiful beaches on Lake Michigan and have plenty of boutique shops, restaurants, antique stores and neighborhood cafe's/coffee shops in within a few block radius. There is no parking included in the stay but the streets around us have plenty of non-permit parking available. Please note Granville is free and no permit required as well as on Lakewood and Hood south of Granville. North of Granville is permit required from 4PM-8AM so make sure to look for permit signs. Visiting Loyola? We are a 10 minute walk from campus! Looking to head to the hip neighborhood of Andersonville? It’s a 25 minute walk/ 1 mile south filled with great nightlife, restaurants and shopping (both budget friendly and high-end)! We are happy to share all our favorite spots to shop and eat around the neighborhood and the city! We live in the house attached with our 2 golden retrievers so please be aware that they will be nearby. They are very friendly! Nearby convenience & grocery stores: - Target: .4 mi/ 9 minute walk - Whole Foods: .3 mi/ 8 minute walk - Aldi: .1 mi/ 4 minute walk - CVS: .1 mi/ 3 minute walk We look forward to hosting you!

Guest favorite

A stone patio is shown featuring a seating area with comfortable wicker furniture. Lush greenery surrounds the space, including trees and well-kept hedges. A coffee table with decor sits at the center, offering a serene outdoor retreat.

Guesthouse in Evanston

4.94 out of 5 average rating, 117 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 . Extra

Top guest favorite

A charming guest house with light-colored siding and a red door is nestled among vibrant flowers in the garden. Large windows invite natural light, surrounded by leafy greenery, creating a peaceful atmosphere that complements the surrounding pollinator garden.

Guesthouse in Evanston

4.98 out of 5 average rating, 263 reviews

Cottage in a Garden

Enjoy the serenity of our secret garden from your private guest house. Enjoy privacy on the covered sun porch. Watch butterflies float by in the pollinator garden. Listen to evening quiet on the patio overlooking the garden. Spin some records from the eclectic collection. Stroll the leafy neighborhood. Stop for a beer at award-winning Temperance Brewery. 5 minute walk to Divvy bike station gives you access to all of Chicago and CTA/Metra train. Short ride to lakefront, Northwestern, downtown.

Guest favorite

A spacious living area features a large stone fireplace, flanked by wooden accents and a mounted moose head. A cozy sofa with decorative pillows faces a coffee table, surrounded by additional seating. Natural light streams in through the nearby window, enhancing the welcoming environment.

Guesthouse in East Rogers Park

4.97 out of 5 average rating, 118 reviews

A bit of the North Woods on Chicago's North Side!

Looking to get away from it all but not TOO far away? Ours is a quiet, screen-free property perfect for a writer’s or artist’s retreat. NU/Loyola parents or alums, stay here when you visit your kids/alma mater. Fantastic renovated livery barn with lots of light, privacy and amenities. Located in Rogers Park, a short walk to Metra and the Red line. Ample street parking nearby. Created for comfort with a splash of Swedish design, enjoy the deck overlooking a tree-filled garden and waterfall.

Guest favorite

A charming three-story home features a white exterior with large windows and a welcoming front porch. The front yard, enclosed by a black fence, showcases greenery and elements of landscaping, providing a pleasant aesthetic along the tree-lined avenue.

Guesthouse in Roscoe Village

4.91 out of 5 average rating, 100 reviews

Charming village within the city

European style first floor apartment in a charming three story home built in 1910. Newly renovated with private entrance, 2 BR, bathroom, spacious living /dining room. Bedrooms have queen beds and ample closet space. Living room includes a pullout couch for an extra guest and a dining area equipped with a coffee machine, tea kettle, microwave , toaster and mini fridge. NO Kitchen available. On a quiet tree lined avenue , free street parking and an easy walk to local shopping bars and dining.

Top guest favorite

A small porch area features a wooden floor and a wooden railing with a lattice design. Two cushioned chairs and a folding table are arranged, creating a cozy spot for relaxation. Natural light filters through the nearby window, enhancing the inviting atmosphere.

Guesthouse in Logan Square

4.98 out of 5 average rating, 301 reviews

Private coach house near transit shops & nightlife

This newly renovated coach house comfortably accommodates 3 adults but can sleep 4. Only a 7 minute walk from the "L" train (CTA blue line to O'Hare airport & downtown). Close to Chicago's Wicker Park and Logan Square neighborhoods with lots of nightlife and dining options within a 10-15 minute walk. The ~750 sqft space features a bedroom and office upstairs; the ground floor has a combined kitchen/living room and one bathroom. 4 guest limit based on city of Chicago occupancy ordinances.

Guest favorite

A metal gate stands at the entrance to the property, flanked by a warm brick facade. A prominent wooden sign reading 'WELCOME' hangs nearby. A call button is mounted on the wall, adding to the inviting entryway.

Guesthouse in Roscoe Village

4.9 out of 5 average rating, 148 reviews

The Roscoe Village Guesthouse

The Guesthouse is located in a village within the city of Chicago. We are in the heart of Roscoe Village and walking distance to the CTA brown line train. We are less than 1 mile west of Wrigley Field and a 20 minute train ride to downtown Chicago. Right outside your door are restaurants, boutique shopping and cafe's. Plenty of free street parking around the house. I offer this unique & personal space to guests when I am away.

Guest favorite

A well-equipped kitchen features dark wooden cabinetry and countertops with a smooth granite finish. Modern appliances, including a stove and refrigerator, are visible. Warm wood flooring complements the space, which is illuminated by natural light coming through a nearby window.

Guesthouse in Evanston

4.92 out of 5 average rating, 108 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.

Top guest favorite

An open and airy living space features a large mounted TV on a rustic wood wall. A sectional couch offers ample seating, with a light-filled skylight above. A world map adorns one wall, complemented by a modern dining table and black chairs in the foreground.

Guesthouse in Oak Park

4.99 out of 5 average rating, 105 reviews

Stylish Coachhouse in lovely Oak Park!

Enjoy the privacy and artistry of your very own coachhouse. The interior is a personalized mix of artistic, industrial and farmhouse. Cool colors, personalized details and local art included. You have your own washer, dryer, complete kitchen, and private patio space. Walk the lovely neighborhood, to the L train, or even to a local brewery.

Guest favorite

A modern kitchen features dark cabinetry and a large wooden island. A vase with flowers is placed at the center of the island, while stainless steel appliances, including a microwave and coffee maker, are neatly arranged along the counter.

Guesthouse in Oak Park

4.89 out of 5 average rating, 499 reviews

Coachhouse in central OP 4 blk to L

Just updated, furnished 1 BR 1 BA apt in Frank Lloyd Wright Historic District. Parking, kitchen, washer/dryer in unit, Air/Heat, Smart TV. Free wifi. Central location: 1 blk to farmers market, near Hemingway / Frank Lloyd Wright attractions. 4 blocks to green line. 20 min ride to downtown Chicago. Available for longer term stays.

Guest favorite

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

4.95 out of 5 average rating, 104 reviews

O'Malley Oasis!

Your home away from home at this centrally-located coachhouse apartment.Queen sized bed, fully equipped eat-in kitchen, relaxing living area with recliner, leather couch and big screen tv. Walk to downtown or explore Chicago via public transportation just a few blocks away. Adorable porch and your own entry. Parking spot included!