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Apartment

Upscale 4BR Retreat: Wicker Park

Photo gallery for Upscale 4BR Retreat: Wicker Park

Living area
Room
Room
Dining
Room

Reviews

8.4 out of 10
Very good
4 bedrooms2+ bathroomsSleeps 8

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet

Spaces

Kitchen
Office
Dining area

About this property

Upscale 4BR Retreat: Wicker Park

Summary:

Welcome to your spacious 4-bedroom getaway in the heart of Wicker Park—Chicago’s most vibrant and eclectic neighborhood. Located on N Damen Ave, this modern apartment is perfect for groups, families, or business travelers looking for comfort, style, and unbeatable access to the city’s top dining, nightlife, and cultural hotspots.



The Space:

What You’ll Love:

✓ 4 comfortable bedrooms — ideal for up to 8 guests

✓ Fully equipped kitchen

✓Reliable wifi

✓ In-unit washer & dryer

✓ Central A/C & heating

✓ Keyless entry for self check-in

✓ Steps to Blue Line (Damen Station) for easy access to downtown & O’Hare

✓ Walk to top-rated restaurants, boutiques, music venues & coffee shops



Whether you're grabbing brunch at Big Star, exploring the shops on Milwaukee Ave, or hopping on the Blue Line to downtown, this location makes it easy to experience the best of Chicago. Enjoy the charm of a local neighborhood with quick access to everything the city has to offer.



Book now and make your stay unforgettable in one of Chicago’s most iconic areas.



Guest Access:

Note: The apartment includes areas on both the 1st floor and basement.



The Neighborhood:

There are lots of great spots to eat nearby—Filipino, Mexican, and Greek restaurants are just a few options worth checking out. You’ll also find some nice cafes and bars in the area if you’re in the mood to relax or grab a drink. And if you need to pick up anything, Target is just a few minutes away.



Getting Around:

It’s a really convenient spot to get around—there are bus stops nearby, like at Damen & Thomas, and the Division station is just a few minutes away. You’ll also find a Divvy bike station close by, and ride-sharing options are always easy to grab when you need them.



Other Things to Note:

For security purposes, ID might be required.



Pet-friendly with prior approval and pet fee. Dogs and cats only. Pets may not be left unattended unless crated, must comply with quiet hours, and are not permitted on furniture. The pet fee does not cover damage to furniture, bedding, rugs, or excessive hair/odor removal.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly

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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
Charge may apply
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Smoking

Smoking is not permitted
🚭 This is a smoke-free spot. Smoking inside = $250+ cleaning fee. 🐾 Pets are allowed in the unit. (dogs or cats). Fee is $100 per pet. Sneaking ...

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 and a first aid kit
Property Registration Number R25000133995

About the area

Chicago

West Town, a neighbourhood in Chicago, is home to this apartment. 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 Millennium Park and Grant Park. Looking to enjoy an event or a game? See what's going on at United Center or Wrigley Field.
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Map
Chicago, IL

What's nearby

  • Presence Saint Mary Of Nazareth Hospital Center - 6 min walk - 0.6 km
  • Milwaukee Avenue - 9 min walk - 0.8 km
  • Humboldt Park - 20 min walk - 1.7 km
  • The Salt Shed - 2 min drive - 1.8 km
  • United Center - 3 min drive - 2.5 km

Getting around

  • Chicago Clybourn Station - 3 min drive
  • Damen Station - 12 min walk
  • Chicago Midway Airport (MDW) - 40 min drive

Restaurants

  • ‪Kasama - ‬4 min walk
  • ‪Colectivo Coffee Wicker Park - ‬3 min walk
  • ‪Nikko Sushi Izakaya - ‬4 min walk
  • ‪Cheba Hut Toasted Subs - ‬3 min walk
  • ‪Oud Coffee and Cafe - ‬6 min walk

Frequently asked questions

Is Upscale 4BR Retreat: Wicker Park pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Upscale 4BR Retreat: Wicker Park?

As of 3 Apr 2026, prices found for a 1-night stay for 2 adults at Upscale 4BR Retreat: Wicker Park on 1 Jul 2026 start from £423, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

What time is check-in at Upscale 4BR Retreat: Wicker Park?

Check-in begins at 3:00 PM.

What time is check-out at Upscale 4BR Retreat: Wicker Park?

Checkout is at 11:00 AM.

Where is Upscale 4BR Retreat: Wicker Park located?

Located in West Town, this apartment building is 0.6 mi (0.9 km) from Milwaukee Avenue and within 3 miles (5 km) of United Center and Michigan Avenue. Humboldt Park and The Salt Shed are also within 1 mile (2 km). Damen Station is 12 minutes by foot and Division Station is 13 minutes.

Reviews

8.4

Very good

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 3 out of 8 reviews
Rating 8 - Good. 4 out of 8 reviews
Rating 6 - Okay. 0 out of 8 reviews
Rating 4 - Poor. 1 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

9.0/10

Cleanliness

8.8/10

Check-in

8.8/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

Reviews

Verified

8/10 Good

John R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place in a great area. Would definitely stay here again!
Stayed 1 night in Sep 2025
Verified

10/10 Excellent

Allison M.

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

Awesome for group of 8!

Place was clean, safe, parking was easy along side streets. Very spacious and reasonably priced! Will stay again!
Stayed 2 nights in Jul 2025
Response from VrboOwner on 4 Aug 2025
Thank you for the wonderful review, Allison! Hope to see you again!
Verified

8/10 Good

Andrea B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location with lots of space. The apartment was very clean but a little run-down (especially in the bathrooms) to be called "upscale." It was quite dark during the day and the kitchen could have been better equipped; there was a Keurig machine but only 3 K-cups in the cupboard (for four people for three nights), for example. Overall, a comfortable stay in a great neighborhood for a girls' trip.
Stayed 3 nights in Oct 2025
Verified

8/10 Good

Heather W.

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

Decent place

Communication was fantastic. The back area kinda creepy to enter in, especially at night, but the apartment was beautiful. It would be a neat idea to clean up the basement outdoor area for a sitting area.
Stayed 2 nights in Jun 2025
Response from VrboOwner on 16 Jul 2025
Thanks for the good review, Heather!
Verified

10/10 Excellent

Alexis B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was a really great communicator! There was a slight issue that was out of their hands with our original location and they immediately figured out another place we could stay instead. They were also very helpful in giving me answers to any questions I asked. The place was super nice and for being in a big city, it was pretty quiet. Check in was super easy and it was really nice being able to take care of it prior to arriving. This was our first experience staying in this type of place and we could not be any happier with how smooth of an experience it was. I definitely recommend staying at a place managed by this host!
Stayed 1 night in Jul 2025
Response from VrboOwner on 4 Aug 2025
Thank you so much for your wonderful feedback! I’m glad I could help make your first experience smooth and enjoyable. It was a pleasure hosting you, and I truly appreciate your recommendation. You’re always welcome back!
Verified

8/10 Good

Evangeline b.

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

Great location a bit worn

We had a good stay. I will say the place has a great deal of wear and tear (walls and baseboards scuffed up, rugs not fully vacuumed as there were some little rocks stuck in them so when walking barefoot would step on them, a few things somewhat broken ie handrail, etc). Otherwise clean and the beds very comfortable. For the amount of background checks that went into verifying that we were good guests I would've expected a more polished place. Great and speedy communication with the host.
Stayed 1 night in Jul 2025
Response from VrboOwner on 4 Aug 2025
Thank you for your feedback. We’re glad you enjoyed the stay and found the beds comfortable. We appreciate your notes on the condition of the unit and will address these with our team to improve. It was a pleasure hosting you!
Verified

4/10 Poor

Sara Pilzer W.

Liked: Location, listing accuracy
Disliked: Check-in, communication
Once we got there, the stay was fine and quiet. However, there is a non-disclosed requirement to share personal information, and only after payment and confirmation. We booked last-minute, at 10am for the next day. We got the typical correspondence from the owner requesting our names and ages, which we shared. A couple hours later, we received a message saying we needed to submit a pic license or passport through a link to a third party service that said "To personalize your stay, use our services, and verify your identity, the details provided in the check-in form may be shared with third parties." We were not comfortable sharing this information without assurances of how the info would be used so I contacted the owner directly to express concerns and to offer to provide additional information directly. We have positive VRBO ratings, I shared links to our professional bios, and offered to help verify identify through other non-open-ended means. The owner said we could share details directly with her, which I did. We woke up to a new message that was sent after midnight saying that we, in fact, needed to use their third party system in order to be given check-in details. Scrambling to finish packing and get to the airport, we were not pleased with this change. Pro Tip: An old student id worked. We didn't appreciate the booking process, privacy concerns and lack of/misinformation. Also, there was an old contact lens on the bathroom floor, so not very clean.
Stayed 1 night in Aug 2025
Response from VrboOwner on 26 Aug 2025
Thank you for sharing your feedback. We’re glad to hear that you found the stay itself to be quiet and comfortable. We also understand your concerns regarding the identity verification process. For security reasons, we use a trusted third-party system to confirm guest details, which is an additional layer of protection for both guests and property. The verification process expectations are set and disclosed in advance for transparency, but we realize it can feel like an extra step—especially with a last-minute booking. We’ll continue to look at ways to make this process feel as smooth and reassuring as possible. We also appreciate you pointing out the cleanliness detail in the bathroom—this has been addressed with our housekeeping team to ensure it does not happen again. Your feedback is very valuable in helping us improve both the booking process and the in-stay experience for future guests. Thank you again for staying with us and for taking the time to share your perspective.
Verified

10/10 Excellent

Derek R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice and clean place. Host was very communicative. Would definitely stay again.
Stayed 1 night in Feb 2026

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