The Greenleaf House—Whole House

Chicago, Illinois
$764 avg/night Minimum Stay 2 Nights
Bed 7

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 12

Max Sleeps

Night 2 nights

Min Stay

The Greenleaf House, built in 1915, is our 3600ft² home with 6 bedrooms, 2.5 baths, & an open floor plan—perfect for gatherings of any kind. We're in the heart of the Rogers Park neighborhood, walking distance from many restaurants & 1 block from Loyola Beach Park. Breakfast is self-serve & included in the cost of the room. In the kitchen you will find bagels, cream cheese, eggs, yogurt, cereal & fresh fruit. The home is run by friendly local folks who are happy tohelp during your stay.

You would have access to the entire house, which has 6 bedrooms, 2.5 bathrooms, and an open, spacious first floor with a modern kitchen, large dining room (seats 12-16), living room with ample and comfortable seating, sound-insulated theater, and a big backyard that is fenced-in and dog-friendly. The house is perfect for hosting parties and events, a weekend getaway with friends or family, or gathering everybody together to celebrate a graduation or wedding. Below you will find a list of the rooms and accommodations.

1 King sized room (sleeps 2)
2 Queen sized room (sleep 2 each)
1 Single Sized room (sleeps 1)
Two lofted Bunk Rooms (Sleeps 1x2) *kids, teens, small adults

TOTAL: 10 people can sleep comfortably in beds, but we also have 2 air mattresses and several couches.

Catering is available upon request.

Two parking spaces are included—one in the front of the house, another in the rear.

The entire first floor is shared space (all the bedrooms are upstairs). You will have access to: a modern kitchen stocked with complimentary breakfast items; a sound insulated theater equipped with Netflix, Showtime and an Xbox; a spacious living room with comfortable seating, a record player and a fine selection of vinyl; a dining room that seats 12-16 people; washer and dryer with free detergent/dryer sheets, and a picnic table and firepit in our big backyard which is fenced-in and dog-friendly.

We like to have everything setup for you and your guests upon arrival. We will communicate with you through the app prior to your reservation to be sure of this. If something unforeseen should occur, our staff is nearby and happy to help. Otherwise, the house is all yours!

The Greenleaf House has become a hub in the Glenwood Avenue Art District of Roger’s Park, where all flavors of creative artists have lived and collaborated for several decades. The Mile of Murals—a community-based public art initiative—begins half a block from our front door. Within easy walking distance you will find a bustling nightlife, small theaters and music venues, several locally-owned eateries, and Loyola Park, which has a great playground and arguably the best sand beach in the city.

Here are a few links about our neighborhood:

https://www.choosechicago.com/neighborhoods/north/rogers-park/

http://www.glenwoodave.org

https://www.rogerspark.com

The Greenleaf House is conveniently located near two major public trains—we are one block from the El (CTA Red Line at Morse Avenue) and three blocks (5-8 minute walk) from the Roger’s Park Metra Station. There are several bus stops within walking distance, including express buses to downtown. It is also never difficult to hail a cab, and Uber/Lyft rides generally arrive in 1-5 minutes after placing a request. For your convenience, we have included links to public transit information below.

CTA Morse Red Line Station:

https://www.transitchicago.com/travel-information/rail-station/-stopid-104/

Metra Rogers Park Station:

https://metrarail.com/maps-schedules/train-lines/UP-N/stations/ROGERPK

Checking out: Check-out time is 12pm noon. Please leave your keys in the door.

Checking Out late: You may checkout late till 3pm, but must be out of your room by 12pm. Feel free to hang out on the first floor, or stow your luggage and explore. If you would like to stay later than 3pm, we are happy to accommodate you so long as it doesn’t interfere with a house rental or special event.

Luggage Storage: There is a storage space in the TV room. It is first come, first serve and has a lock and key. If the key is in the lock, it is free to use. Please use only if your room is unavailable.

Laundry: Feel free to use the laundry any time except 12pm - 3pm. That is when we wash sheets and towels used by our guests. Detergent and dryer sheets are provided.

Security cameras: For your safety, there are security cameras inside the common areas and outside the property. We don’t actively monitor them unless something happens. Please do not tamper with the security cameras.

Shared Space: The first floor is a shared space. This includes the TV room (which has Netflix). Feel free to hang out and interact with other guests.

Dogs: Dogs are allowed for an extra $10 per night. We accept Venmo, PayPal, cash or check. See the dropbox in the kitchen for further instructions.

100% Smoke Free: Smoking is prohibited inside the house. Please smoke outside.

Parking: Parking spots are $10/night when available. They cannot be reserved on the app. Ask your host about availability. We accept Venmo, PayPal, cash or check. See the dropbox in the kitchen for further instructions.

Visitors: Visitors are allowed on the first floor until 11pm.

Quiet Hours: As courtesy to other guests, quiet hours are 11pm to 7am.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    4 Total Pets Pet Friendly Welcoming Dogs Only
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    7 Bedrooms Bed Sheets Provided
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Gas Grill
  • BATHROOMS

    2.5 Bathrooms Hair Dryer Shower/tub Combination Towels Provided
  • ENTERTAINMENT

    Books Games TV With Cable/satellite Service
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Toys
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 12:00 PM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 12

Map Map

School District Rates & Availability

Review Review

  • Dorinda N.

    Submitted Jan 4, 2026

    Stayed Dec 26, 2025

    The house was perfect for our needs. we all had a great time. It was easy and comfortable. Thank you!

  • Kristin L.

    Submitted Oct 17, 2025

    Stayed Oct 1, 2025

    Ideal location for a large family or group.

  • Megan H.

    Submitted Oct 2, 2025

    Stayed Sep 18, 2025

    we spent a long weekend here while visiting our daughter at loyola. location was absolutely perfect--easy walk to loyola and edgewater, and quick walk to the red line too! plenty of space for all twelve of us, 3 parking spots was huge! we'll be back!

  • John T.

    Submitted Sep 15, 2025

    Stayed Sep 12, 2025

    Great location for our stay and we enjoyed it. Only drawback was not being able to get college football on the tv on Saturday; but perhaps that was user error.

  • Vera D.

    Submitted Jun 28, 2025

    Stayed Jun 19, 2025

    In the bedrooms the temperatures varied and didn't seem to be adjustable.Basically, they were content.

  • Stephanie O.

    Submitted May 18, 2025

    Stayed May 16, 2025

    This was a lovely place to meet up with multiple friends. It’s a large house, clean, and spacious. The host was communicative and friendly

  • Timothy W.

    Submitted Mar 23, 2025

    Stayed Mar 14, 2025

    Very nice clean property. Pretty much had everything we needed. Some of the furniture was a little less than comfortable to sit on. But we made do.

  • Christian P.

    Submitted Mar 10, 2025

    Stayed Mar 7, 2025

    As advertised.

  • Becky F.

    Submitted Mar 4, 2025

    Stayed May 7, 2024

    We stayed here for a Loyola Graduation. The location was terrific and the space accommodated a lot of guests for a backyard celebration. The host was very responsive when we asked if we could get the yard mowed and outside area cleaned up before the party.

  • Tammy S.

    Submitted Jun 18, 2024

    Stayed Jun 16, 2024

    The house was big enough for whole family. It was also in a great location. However, the locked bedroom doors were a big inconvenience and the carpeting was disgusting. So dirty. Did not like walking in it without shoes.

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Total

Includes taxes and fees
$764+
View details