Vacation rentals in Monroe Harbor

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Top-rated vacation rentals in Monroe Harbor

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Guest favorite

Guesthouse in Little Italy

4.99 out of 5 average rating, 783 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.

Oct 25 – Nov 1

G$30,010 GYD per night

Guest favorite

Home in Pilsen Historic District

4.96 out of 5 average rating, 316 reviews

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

House is perfectly located within walking distance of Pilsen's best attractions. Home is furnished and newly renovated with the idea of making your stay as comfortable as possible. Walking distance from Thalia Hall and many other great restaurants and coffee shops. For your convenience there is a "corner store" steps from the home where you can purchase food and beverage items. The whole apartment is professionally cleaned after every guest no matter how many days they have stayed. Fresh sheets and towels are provided for all guests as well. Walking distance from local favorites: Simone’s, Honky Tonk BBQ, Dusek's/Punch House/Thalia Hall, 5 Rabanitos, Furious Spoon, S.K.Y and HaiSous. Located 2 miles South West of Downtown Chicago. Extremely close to South Loop and West Loop. Amenities: - Washer and Dryer (located in unit) - Granite counter tops - All new appliances - Tiled bathroom - Central Heat/AC - Private back deck - Closet space All access, full kitchen, washer and drier in apartment. Private entrance with Keyless entry. Available at any time, happy to answer any questions you may have. Interaction will be dictated by guests. This is a vibrant family neighborhood with character, art, great food, and culture. Walk to amazing restaurants, bars, and coffee shops, including local favorites Simone’s, Honky Tonk BBQ, 5 Rabanitos, Furious Spoon, S.K.Y, and HaiSous. Close to major Chicago highways: I-190: Kennedy Expressway I-290: Eisenhower Expressway I-55: Stevenson Expressway I-90/94: Chicago Skyway, Dan Ryan Expressway, Kennedy Expressway, Jane Addams Memorial Tollway Public transit easily accessible: CTA Bus #8, 18, 60 CTA Trains: Blue, Pink and Orange Lines Divvy Bike Rental Station one block away Permit Parking $6-10 dollar Uber to Downtown

Jan 29 – Feb 5

G$29,196 GYD per night

Guest favorite

Apartment in Lincoln Park

4.98 out of 5 average rating, 296 reviews

Redesigned Lower Level Studio in Historic Building

The space is very comfortable, quiet and cozy. There are new cabinets, granite counter tops, all new appliances and a washer and dryer. Guests sleep on a king size tempur-pedic mattress or a queen size trundle style pull out sofa. There is hi-speed wi-fi, cable TV (Showtime), 55' flat screen TV and a wood burning fireplace. The bathroom is immaculate and includes a full bathtub with shower. This is a private apartment and you will have access to the entire suite. There is a back and front door with adequate lighting and easy access for guests. My family and I live next door and I will be available at our guests convenience. I am happy to provide any information, recommendations, directions etc.. I am easy to reach and am always available but will not intrude on our guests privacy. This unit is on a beautiful tree lined street in the heart of Old Town, close to St. Michael's Church, Steppenwolf Theater, and the Second City Improv Theater. The location allows for easy access to all of Chicago by either train, bus, or car. The blue and brown line train stations are within walking distance. Street parking is readily available and no permits are necessary. A Chicago Cab or Uber can get you to Milleniumm Park in approx. 15 minutes. Four adults can comfortably stay in this unit. The king size tempur_pedic mattress is the pinnacle of comfort and the queen size trundle style pull out sofa is comparable to sleeping on an actual queen size mattress. The queen size bed could comfortably fit 3 children. There is street parking readily available but I can provide an assigned space behind the building if necessary, for additional cost.

Sep 23 – 30

G$26,587 GYD per night

Guest favorite

Guest suite in East Pilsen

4.93 out of 5 average rating, 114 reviews

Entirely Private Suite - Urban Oasis - Pilsen/UIC

Welcome to a brand new, entirely private, spacious and peaceful oasis in East Pilsen-UIC with its own smartlock/entry system and self check in. Located at the intersection of some of the hottest neighborhoods, restaurants, concert and tourism venues, and minutes from the Loop! Amenities: Full bath with a luxurious spa shower, cable, wifi, flatscreen tv, refrigerator, Keurig coffeemaker, hair dryer, iron and toiletries. The best part... a set of glass doors that open to a lovely private deck.

Jul 6 – 13

G$23,853 GYD per night

Guest favorite

Apartment in Humboldt Park

4.98 out of 5 average rating, 106 reviews

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Sep 20 – 27

G$25,515 GYD per night

Superhost

Guesthouse in Bridgeport

4.93 out of 5 average rating, 321 reviews

Private Studio in Bridgeport, Chicago

A bright studio guesthouse, perfect for business travelers, a couple’s getaway, personal retreat, or a solo adventurer. Has a kitchen sink, cabinet space for your non-perishable items, a microwave, mini-fridge, and Keurig. We provide plates, flatware, mugs, and glasses. The studio offers the privacy of your own bathroom and shower facilities. You'll rest well in a full-size Murphy bed, with sufficient storage for all your travel items. A couch is available for a third guest if needed.

Sep 26 – Oct 3

G$20,247 GYD per night

Guest favorite

Apartment in West Town

4.96 out of 5 average rating, 262 reviews

Turquoise Wonder - Clean, Cozy & Stylish Apt

Clean, stylish & comfy apartment, perfect for 1 or 2 adults. 2 guest maximum, no children. Close to public transit (bus), wonderful restaurants & bars, gift shops, boutiques, coffee shops, parks, museums & more. Ukrainian Village/Humboldt Park area. King size comfortable Tempurpedic mattress. Central heat, A/C. Nice kitchen w/ stainless appliances, excellent bathroom, shower & tub. Free street parking. Relax in the comfort of the Turquoise Wonder! Enhanced cleaning protocols for COVID.

Apr 9 – 16

G$21,223 GYD per night

Guest favorite

Home in West Loop

4.97 out of 5 average rating, 318 reviews

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.

Aug 24 – 29

G$36,358 GYD per night

Guest favorite

Apartment in Pilsen Historic District

4.86 out of 5 average rating, 232 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond.

Aug 15 – 22

G$15,760 GYD per night

Guest favorite

Guest suite in Bronzeville

4.95 out of 5 average rating, 153 reviews

Bronzeville Beauty: Modern Style + Historic Charm

Come relax and take in Chicago's historic Bronzeville neighborhood. Stay in the bright and sunny garden unit of a fully renovated landmarked home built in 1887. We are located across from a neighborhood park with excellent access to CTA transit. Walkable to Lake Michigan, Lakefront Trail, White Sox stadium, IIT. Very close to McCormick Place, Hyde Park, and Chinatown. If you drive, free street parking is readily available in front of our home.

Sep 19 – 26

G$27,362 GYD per night

Guest favorite

Home in Bridgeport

4.95 out of 5 average rating, 120 reviews

Cozy & Modern Chic 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.

Dec 21 – 28

G$24,851 GYD per night

Guest favorite

Apartment in Gold Coast

4.89 out of 5 average rating, 140 reviews

Charming Gold Coast One-Bedroom Near Downtown!

Perfect Gold Coast studio near downtown, the lake and everything else! We are nestled in the Gold Coast in an excellent location. Public Transportation, restaurants, shops, museums and grocery stores are all steps away! The apartment is within an art deco style mid rise and has everything you need to be your home away from home while you're visiting the city of broad shoulders. Chicago Shared Housing Registration Number: R21000073420

Feb 16 – 23

G$23,605 GYD per night