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

An outdoor patio with a large umbrella, wicker furniture, and a barbecue grill.
Property video
A modern kitchen with wooden cabinets, stainless steel appliances, and a wine rack.
A living room with a beige sofa, a glass coffee table, and a fireplace.
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.

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Private garden
    A rare find — relax in the peaceful, private garden space.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Humboldt Park

Popular amenities

  • Balcony
  • Massages in spa
  • Kitchenette
  • Toys
  • On-site fitness centre
  • Barbecue

Explore the area

View 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

Rooms & beds

5 bedrooms (sleeps 15)

Bedroom 1

1 King Bed, 1 Queen Bed and 2 Single Beds

Bedroom 2

1 Queen Bed and 1 Single Bed

Bedroom 3

2 Queen Beds and 2 Single Beds

Bedroom 4

1 Queen Bed

Bedroom 5

1 Queen Bed

Living Room 1

1 Single Futon

3 bathrooms, 1 half bathroom

Bathroom 1

+1
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shower only · Jetted bathtub · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 3

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Jetted bathtub · Shampoo · Hair dryer

Bathroom 4

Towels provided · Toilet · Hair dryer

Spaces

Deck or patio
Kitchen
Kitchenette
Balcony
Separate dining area
Number of living rooms
Outdoor play area
Garden
Dining area

Add dates for prices

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About the area

Chicago

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. Looking to enjoy an event or a game? See what's going on at United Center or Wrigley Field. Relax and indulge in the area's health/beauty spas, or seek out an adventure with hiking and cycling nearby.
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Map
Chicago, IL

What's nearby

  • The 606 - 6 min walk - 0.6 km
  • Humboldt Park - 6 min walk - 0.6 km
  • 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
  • ‪Handlebar - ‬7 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.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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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

10/10

Check-in

10/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time! Place was clean and in a great location.
Stayed 3 nights in Aug 2026
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
I rented the property as a surprise for my husband and 9 friends to celebrate his 50th birthday. They enjoyed it. They loved sitting outside on the rooftop and having the workout equipment. The accommodations were nice. The property was clean. Communicating with Nancy as I was planning the trip was very informative and timely. Nancy is a great host and I would definitely recommend this property.
Stayed 3 nights in Sep 2026
Response from VrboOwner on 5 October 2026
Evona- thank you so much for your kind review. I was such a pleasure hosting your group for such a special milestone. I’m so glad everyone enjoyed the home, and that you found the planning and communication helpful. I would be so happy to welcome you back anytime!
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
Response from VrboOwner on 14 October 2025
Thank you for your review. It was pleasure to host you.
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
Response from VrboOwner on 2 June 2025
Thank you for being wonderful guests as well. We hope you will return.
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
Response from VrboOwner on 4 August 2025
Thank you Kobie for your review. Iʼm glad the stay was memorable.
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
Response from VrboOwner on 14 October 2025
Great to host you and your group.
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
Response from VrboOwner on 29 May 2025
Thank you for your review. Wonderful to have hosted you and your family Dawn. We hope it wonʼt be the last.
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

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
Great stay and communication. Would definitely recommend for larger parties. Nancy gave us great ideas as well. Thanks!
Stayed 3 nights in Sep 2025
Response from VrboOwner on 14 October 2025
Thank you for your review. Hope to host you in the future.
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
Response from VrboOwner on 30 September 2024
Thank you for staying here with your family Tom. You took wonderful care of the home. We hope you will return again. For clarity, the primary bedroom’s switch tripped, which needed to be reset; something very minor. I don’t want future guests to think the entire house was without power :)
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
Response from VrboOwner on 14 October 2025
Thanks Jennifer. Yes, two bedrooms are downstairs so itʼs inevitable to hear some noise since the main level is above.
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
Response from VrboOwner on 14 October 2025
Thank you for your review. Iʼm so glad you chose us to make beautiful memories with your family.
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
Response from VrboOwner on 22 August 2024
Thank you Max for the great feedback. We always look to improve our guest experience. Much appreciated. We hope to host you again.
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
Response from VrboOwner on 9 April 2024
We are happy you chose Casa Maplewood to host your sister's special occasion. We look forward to hosting you again.
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
Response from VrboOwner on 4 August 2025
Thank you Annemarie. The city unfortunately moves bins during trash pick up. These can be moved to the side to allow room to enter the garage.
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
Response from VrboOwner on 25 September 2024
Keith- thank you for the feedback. I’m glad we exceeded your expectations. We look forward to welcoming your group next year.
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
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