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Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat

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Photo gallery for Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat

A beach with people swimming and a boat in the water, and a city skyline in the background.
Property video
An outdoor patio with a large umbrella, wicker furniture, and a barbecue grill.
A spacious living room with a light-colored sofa, a glass coffee table, and a dark wooden cabinet. A staircase with a wooden railing leads to another room.
A living room with a beige sofa, a glass coffee table, and a fireplace.

Reviews

9.8 out of 10
Exceptional

Entire home

5 bedrooms4 bathrooms4000 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Gym

Explore the area

View in a map
Chicago, IL
  • Place, The 606
    ‪6 min walk‬
  • Place, Humboldt Park
    ‪6 min walk‬
  • Place, Milwaukee Avenue
    ‪9 min walk‬
  • Airport, Chicago, IL (ORD-O'Hare Intl.)
    ‪28 min drive‬

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About the neighborhood

Chicago

Located in West Town, this vacation home is a leisurely stroll from sights such as Humboldt Park and Milwaukee Avenue. The vacation home includes a kitchen, a fireplace, and a balcony.
View more Vacation Homes in ChicagoOpens in a new window

What's nearby

  • The 606 - 6 min walk - 0.4 miles
  • Humboldt Park - 6 min walk - 0.4 miles
  • Milwaukee Avenue - 9 min walk - 0.5 miles
  • The Chop Shop & 1st Ward - 13 min walk - 0.7 miles
  • Concord Music Hall - 14 min walk - 0.8 miles

Getting around

  • Chicago Clybourn Station - 3 min drive
  • Western Station (O Hare Branch) - 13 min walk
  • Chicago Midway Airport (MDW) - 41 min drive

Restaurants

  • ‪Dunkin' - ‬7 min walk
  • ‪Wolf & Company - ‬9 min walk
  • ‪Chipotle Mexican Grill - ‬5 min walk
  • ‪Super Burrito - ‬5 min walk
  • ‪Handlebar - ‬7 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat

An ideal retreat for special occasions in Wicker Park. This spacious home is a celebration of contrasts. An eclectic style carefully gathers various periods, styles & interesting recycled elements while creating cohesiveness with modern design. A wide and long, open-floor concept in the heart of the city, with three separate floors. An ideal retreat with tons of light, space and privacy should you prefer to close your bedroom. Perfect for a relaxing vacation or special occasion. A fully equipped chef’s kitchen + wet bar + family room leading to your outdoor deck and rooftop garage. The rooftop garage deck is equipped w/ a Weber grill and sectional seating.

Total bed count: seven queen size beds, two twin foldout bed cots (memory foam), one twin, one floor air mattress, one full size futon, one twin trundle. Three bedrooms are on the second floor with two full bathrooms, vaulted ceilings, washer+dryer. Two bedrooms and third bathroom in the lower level (in-law suite), with an additional living room and kitchenette.

All beds have been comfortably laid out with plenty of room to spread out; Plush beds and cozy organic sheets, large walk-in closets to store luggage. A private spa-like Primary Bath features Italian travertine stone, Zero-entry Steam Shower, oversized jetted Jacuzzi tub fit for two, double sink Vanities. The home has been upgraded with a tankless water heater so your guests never run out of hot water.

10 min walk to Blue line (Western or Damen Stops). The 606 Trail is only 2 blocks away; a 2.7 mile trail and green space for runners and families alike. 5-10 drive to other popular neighborhoods- Logan Square, Bucktown, Humboldt Park, Ukrainian Village; 10-15 min drive to Wrigleyville, Lakeview, Lincoln Park; 15-20 min drive to Fulton Market/West Loop/River North. 25-40 min drive to either O'hare or Midway International Airports.

Restaurants and bars are within a 10 min walk to the popular corners of North Ave/Milwaukee/Damen. 20min Uber to: The Mag Mile,Navy Pier, Soldier/ Wrigley Field, United Center, Millenium Park, McCormick Pl, and Museum Campus.

Fast fiber optic Wifi- 250 mbps. The home is smart temperature controlled with room sensors to help manage hot+cold spots for your comfort, plus a Nest smoke+carbon monoxide detector.

Please note the garage comfortably fits two midsize vehicles or one large SUV.
The vacation home is air-conditioned and features a kitchen, 3.5 bathrooms, and a balcony. There's space to spread out with 5 bedrooms and a dining area. Guests can expect to find free WiFi and a Smart TV with a DVD player. The bathroom offers a jetted tub and hair dryers. Other standard amenities include a washing machine, a fireplace, and a coffee maker.

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Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Massage

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Kitchenette
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bed sheets provided

Bathroom

  • 3.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Jetted bathtub
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • Books
  • DVD player
  • Games
  • Smart TV
  • Stereo

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Upper floors accessible by stairs only
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • On a lake

Things to do

  • Gym
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Hiking/biking trails nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Deadbolt lock
  • Fire extinguisher
  • First aid kit

General

  • Garden
  • Unit size: 4,000 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in available
Minimum check-in age: 35

Check-out

Check-out before 11:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Strip any used beds, gather used towels, and store extra beds
Remove personal items and take out the trash
Turn off the lights, lock the doors, and return the keys
Do not leave any trash on the ground under any circumstances. Access the alley’s trash bins by going through the garage. Push the white button that’s on the wall. Find a trash bin and recycle bin.
Remove any decorations.
Failure to complete these may result in a negative review from the host.

Rules

All guests’ names and ages submitted at the time of booking. Only confirmed guests permitted. No outside visitors.
Respect our neighbors. Rooftop is off limits 8pm Sun-Thurs; 9pm Friday-Saturday. No smoking on the property, including decks (cigarette flickering)
Quiet block. We respect our neighbors. Disruptive gatherings that appear “frat-like” (i.e. music, beer pong, drinking games) are not permitted.

Pets

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
  • Check-in: 3:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 35
Property Registration Number 60622, R26000141386

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

Additional information about polices, regulations, and more:

  • There are no elevators.

Frequently asked questions

What's there to see around this vacation home?

This vacation home is situated in West Town within a short 8-minute walk of Humboldt Park and also 13 minutes on foot from Milwaukee Avenue. You'll also find United Center and Michigan Avenue within a short drive.

Is there parking available at Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat?

Yes, there is a garage.

Is there a spa available at this vacation home?

Spa services at the vacation home include massages.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

What do couples enjoy most about Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat?

Amenities that appeal to couples at this lakeside vacation home include a fireplace, a jetted bathtub, and a kitchenette.

Does Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat have a hot tub?

No, but all house at this vacation home have jetted bathtubs.

Does this vacation home provide breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay free of charge?

No, pets aren't allowed at this vacation home.

Does Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat have connecting rooms available?

No, this vacation home doesn't feature connecting guestrooms.

What is the closest airport to this vacation home?

The closest major airport to this vacation home is Chicago Midway Airport (MDW), which is 14.5 mi away (41 minutes by car). Another top airport is Chicago O'Hare Intl. Airport (ORD), which is located 15.4 mi away (34-minute drive).

Are there rooms with balconies at Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat?

Yes, every house at Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat comes with a balcony.

Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 31 out of 36 reviews
Rating 8 - Good. 5 out of 36 reviews
Rating 6 - Okay. 0 out of 36 reviews
Rating 4 - Poor. 0 out of 36 reviews
Rating 2 - Terrible. 0 out of 36 reviews

9.8/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay, in a cool neighborhood. Awesome patio to hang out. Nancy was super helpful and responsive
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay and exceeded our expectations
Stayed 5 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place for a group!

Nancy was a great host and she place was even better!
Stayed 2 nights in Apr 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent stay

This house was amazing for our girls trip to Chicago and the host was very responsive and accommodating!
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend trip

Was a wonderful stay at an even better place! The host was excellent at communicating and it made the stay much better and easier
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay!

Myself and some friends celebrated a wonderful weekend in Chicago at this exceptional property. The host was also just fantastic.
Stayed 2 nights in Apr 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice apartment in a beautiful neighborhood.
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay!

Had a wonderful stay at Nancy's home with a few friends. Very spacious with comfortable beds. Would recommend.
Stayed 2 nights in Mar 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy

Great stay

Great house. Location could be a bit better.
Stayed 3 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home with spectacular back deck!

Wonderful experience and Nancy was a perfect hostess.
Stayed 3 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great space for large families

We stayed over Memorial Day weekend with our kids and grandkids ages 9 months to 10 year old and was plenty of room and areas to spread out. House was very clean location felt very safe. Host was great answering all our questions.
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Bachelor Party Stay

Great property in an exquisite neighborhood. Everything was accessible and close by. Highly recommend.
Stayed 3 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay and communication. Would definitely recommend for larger parties. Nancy gave us great ideas as well. Thanks!
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing house in a great location

We loved our weekend here. Had a big group of friends and there was plenty of space for us to sleep and hang out. The back patio was especially comfortable. We also loved the neighbourhood and thought it was one of the best places in Chicago. Would absolutely stay here again
Stayed 3 nights in Aug 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very nice stay in Wicker Park Area

The home was very clean and the host was great at communicating. We had a couple of power issues at the house so that should probably be looked into but outside of that it was a very comfortable stay in a good neighborhood.
Stayed 2 nights in Sep 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place and worked well for our family. Only tiny complaint was that if you stayed in the downstairs bedrooms if people were in the kitchen it was very loud. Otherwise it was perfect.
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay in Chicago for our daughter’s wedding. The host responded promptly when I had questions, and she was very accommodating relative to our family’s needs. She even had toys for our grandchildren to play with! The neighborhood is great! We would definitely start here again!
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent stay

We spent weekend for my daughter engagement. It was an excellent place with all amenities in a good location. Had a pleasant weekend with all my family and friends. Host was very courteous and friendly. Would love to stay again
Stayed 2 nights in Feb 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great experience all around

Would highly recommend to anyone staying in Chicago with a large group. Nancy was super communicative, the house was clean and very spacious, and the deck was a big plus. We had a group of 15 and the place slept everyone comfortably.
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place for a large group

I rented this property for my sister’s bachelorette party. It was perfect for our large group! The door lock had some technical issues, but the hose is very responsive. I would recommend!
Stayed 2 nights in Apr 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Windy City

House was comfortable for all guests. Easy access. Good location. Garage was a plus but a tight fit to get into with a large vehicle from the narrow ally and several trash and recycling bins. Roof top deck was a great space to socialize.
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great everything

10 From our company in for a trade show. For the past few years we have used VRBO to book a house for our entire group. Windy City Retreat was by far the best. Great accommodations for nightly communal dinners instead of dining out. Plenty of beds and bath space. Hope to return again.
Stayed 5 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family fun

House worked well for all of us. We enjoyed the multiple gathering spots, especially the outdoor space when weather allowed. Easy access to the 606 trail. Nancy was great about letting us know about events happening that could affect travel plans, as well as giving recommendations for restaurants nearby.
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Incredible Chicago Stay

Spent the weekend and this incredible house celebrating a friend. This spacious incredible property is the perfect combination of function and relaxation with an incredible porch and tons of room and space. Nancy was so incredibly attentive and went above and beyond to check and make sure everything we needed was taken care of and then some! Would def recommend for anyone looking to do Chicago the right way!
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family reunion/Birthday

The place was absolutely perfect for all of my siblings and spouses. We were able to spend quality time with each other! Nancy was very accommodating and was very quick to respond to any questions and gave us some great recommendations. I highly recommend!
Stayed 2 nights in Oct 2023