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Guesthouse vacation rentals in Chicago

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Top-rated guesthouse rentals in Chicago

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

Guest favorite
Guesthouse in Chicago
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.
$114 per night
Guest favorite
Guesthouse in Evanston
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.
$99 per night
Guest favorite
Guesthouse in Chicago
Entire private coach house near transit, 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.
$108 per night

Popular amenities for Chicago guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Oak Park
Coachhouse in central OP 4 blk to L
$150 per night
Superhost
Guesthouse in Chicago
Coach house Wicker Park- Bucktown
$135 per night
Guest favorite
Guesthouse in Wheaton
Cozy private coach house in Wheaton
$111 per night
Guest favorite
Guesthouse in Evanston
Coach House Art Studio, By Downtown & Northwestern
$150 per night
Guest favorite
Guesthouse in Chicago
The Rectory
$192 per night
Guesthouse in Dolton
THE STUGA (swedish for small house)
$66 per night
Guesthouse in Chicago
Accessibility to Midway Airport&Downtown!
$72 per night
Guesthouse in Miller Beach
Dream Retreat Guesthouse, Indiana Dunes Nat’l Park, 10 min hike to Beach
$113 per night
Guesthouse in Chicago
The Midway Flat
$114 per night

Guest house rentals with a patio

Superhost
Guesthouse in Chicago
Private Coach House / Easy Commute
$109 per night
Guest favorite
Guesthouse in Villa Park
Tranquil Pondview +New Kitchen
$120 per night
Superhost
Guesthouse in Chicago
Cozy 1 bed Garden unit 5 minutes to Midway Airport
$45 per night
Guest favorite
Guesthouse in Chicago
2 br, 2 bt, detached, UChicago Coachman's House
$241 per night
Superhost
Guesthouse in Oak Park
Adorable two bedrooms / Kitchen, Gym. and deck
$185 per night
Guest favorite
Guesthouse in Chicago
MultiManor: A Renovated Bucktown Coach House
$100 per night
Superhost
Guesthouse in Wheaton
Guesthouse Adjacent to Wheaton College
$197 per night
Guest favorite
Guesthouse in Chicago
Logan Square Coach House
$84 per night
Guest favorite
Guesthouse in Evanston
Chic coach house near the beach and campus
$85 per night
Guest favorite
Guesthouse in Chicago
Botanical BnB. House in Avondale/Logan Square.
$100 per night
Guesthouse in Chicago
Historic Washington-Hyde Park Greystone
$167 per night
Guest favorite
Guesthouse in Chicago
Beautiful Roscoe Village/Hamlin Park 4 bed 3 bath
$450 per night

Guest house rentals with a washer and dryer

Superhost
Guesthouse in Chicago
Private Studio in Bridgeport, Chicago
$55 per night
Guest favorite
Guesthouse in Countryside
Cozy Cottage Minutes from Downtown Chicago
$95 per night
Guest favorite
Guesthouse in Lake Forest
Large Luxury Guest Apartment in the North Shore
$200 per night
Guest favorite
Guesthouse in Oak Park
Stylish Coachhouse in lovely Oak Park!
$113 per night
Guest favorite
Guesthouse in Chicago
Quiet, Cozy 1-Bedroom Carriage House in Chicago
$92 per night
Guest favorite
Guesthouse in Chicago
The Roscoe Village Guesthouse
$77 per night
Guest favorite
Guesthouse in Roselle
Roselle Studio
$84 per night
Guest favorite
Guesthouse in Villa Park
Eclectic Coach House Apartment
$125 per night
Guest favorite
Guesthouse in Lake Forest
The Green Door - safe and calm with walkability
$94 per night
Guest favorite
Guesthouse in Arlington Heights
Cozy Chicago Suburban Apartment
$74 per night
Guest favorite
Guesthouse in Evanston
Cozy Guesthouse near NU - next to Lee Street Beach
$152 per night
Guest favorite
Guesthouse in Chicago
Charming private coach house
$200 per night

Quick stats about guesthouse rentals in Chicago

Total rentals

70 properties

Wifi availability

70 properties include access to wifi

Rentals with dedicated workspaces

40 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

6.8K reviews

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