Entire home

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

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. - Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat (Chicago)
Property video
A modern kitchen with wooden cabinets, stainless steel appliances, and a wine rack. - Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat (Chicago)
An outdoor patio with a large umbrella, wicker furniture, and a barbecue grill. - Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat (Chicago)
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. - Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat (Chicago)
Consider a stay at Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat and take advantage of a garden, a playground and laundry facilities. Treat yourself to a massage or other spa services. Free in-room WiFi, with a speed of 500+ Mbps (good for 6+ people or 10+ devices), and a gym are available to all guests.

Reviews

9.8 out of 10
Exceptional

Entire home

5 bedrooms4 bathrooms4000 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Gym

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About this property

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.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Massage

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Onsite parking options include a garage

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets 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
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre
  • 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)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden
  • Unit size: 4,000 square feet

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Policies

Check-in

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

Check-out

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

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 to complete the following before checking out:
Strip any used beds, gather used towels and store extra beds
Remove personal items and take out the rubbish
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.

Pets

Pets not allowed

Children and extra beds

Children are welcome

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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that 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
Property Registration Number 60622, R26000141386

We should mention

This property does not have any lifts

About the area

Located on a lake, this holiday home is in West Town, a neighbourhood in Chicago. Michigan Avenue and Navy Pier are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Lake Michigan and Millennium Park. Travelling with kids? Make time for Lincoln Park Zoo, or head to an event or a match at United Center. Relax and indulge in the area's health/beauty spas, or seek out an adventure with hiking/biking trails and cycling nearby. Visit our Chicago travel guide
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Map
Chicago, IL

What's nearby

  • A train on an elevated track above a pedestrian walkway.
    The 606
    6 min walk - 0.6 km
  • A riverside path with a stone edge, lush greenery, and yellow flowers.
    Humboldt Park
    6 min walk - 0.6 km
  • A nighttime cityscape with illuminated buildings and a river.
    Milwaukee Avenue
    9 min walk - 0.8 km
  • The Chop Shop & 1st Ward
    13 min walk - 1.1 km
  • Concord Music Hall
    14 min walk - 1.2 km

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
  • Boulevard Sports Lounge
    4 min walk

Frequently asked questions

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

No, pets are not allowed at this property.

How much is parking at Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat?

On-site parking is available at the property.

What time is check-in at Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat?

Check-in begins at 3:00 PM.

What time is check-out at Live Like a Local. 10min walk to Train. Rooftop+Garage. 3-Level Spacious Retreat?

Checkout is at 11:00 AM.

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

This family-friendly Chicago holiday home is located on a lake, within a 15-minute walk of Humboldt Park and Milwaukee Avenue. United Center is 2.7 mi (4.3 km) away. Western Station (O Hare Branch) is 13 minutes by foot and Damen Station is 15 minutes.

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

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 30 out of 35 reviews
Rating 8 - Good. 5 out of 35 reviews
Rating 6 - Okay. 0 out of 35 reviews
Rating 4 - Poor. 0 out of 35 reviews
Rating 2 - Terrible. 0 out of 35 reviews

9.8

Cleanliness

9.6

Location

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

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

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
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

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

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

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

Wonderful stay.

We had an exceptional time. Place was very accommodating for our large group. Plenty of rooms and beds. The kitchen was well stocked and had everything we needed. The outdoor area was wonderful. 2 garage spots very helpful. Place was clean and really nice. The steam shower was an absolute bonus. Robes in the bathroom was a nice touch. Overall extremely pleased with our stay. Highly recommend. We will be back.
Stayed 2 nights in Nov 2023
Verified review

10/10 Excellent

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

Great stay in Wicker Park

As a group of four families, 16 people, we booked months ahead of our stay. The host, Nancy was extremely communicative by reaching out early on and just in advance of our stay. She was thoughtful and offered restaurant recommendations and suggested things to do. Upon hearing that we had an infant in our group, we were offered a crib and toys for the older kids to play with during our stay. The property was very nice, clean and comfortable. Na
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

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

Fantastic Bachelor Party Weekend!

If you are on the fence about which home to book in Chicago PICK THIS HOUSE. The location is perfect (walking distance to many bars/restaurants/coffee shops and centrally located to all the best neighborhoods), the home was extremely clean and tidy, and the communication with the awesome host was streamlined and efficient. We stayed here for 3 nights for a bachelor trip and the space/layout was perfect. The space is even larger than it seems, and easily supports groups of 10+ people. We loved hanging out in the upstairs patio and exploring the town. I can’t wait to return and stay here with family, as the value is unmatched in this beautiful home. 10/10!
Stayed 3 nights in Jul 2024
Verified review

8/10 Good

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

Pleasant and convenient accommodations

We had a nice time and the hostes, Nancy was attentive with flowers and treats waiting when we arrived. She also let us store our bags before the check in time. There were areas where the house was a little messy (not dirty). A fresh sink sponge was needed and clearer entry and exit instructions would have been helpful. Perhaps a notebook with some house idiosyncrasies and intructions (as they do in other VRBO's) would be a good idea. It was a nice neighborhood and good location to visit Chicago.
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

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

Great spot for a guys' getaway

This property was perfect for a 6-friend meetup. We all had our own bedrooms and plenty of space to have side conversations and activities. The main floor had two living spaces and a well-appointed kitchen. Downstairs, another living space was perfect for playing video games and had a kitchenette, fridge, and multiple bedrooms. The property was clean and none on my friends had any complaints about living conditions.The neighborhood is quaint and quiet but there are restaurants, bars, and coffee shops close by as well as a liquor store and CVS that can fulfill all your shopping needs for a quick guys' getaway. The rooftop patio is a nice plus for post-party coffee catchups.If you're looking to stay in Wicker Park, I would highly recommend this property.
Stayed 3 nights in Apr 2025
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

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

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
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

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

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 stay and communication. Would definitely recommend for larger parties. Nancy gave us great ideas as well. Thanks!
Stayed 3 nights in Sep 2025