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Book Online or call HomeAway Booking Assistance 888-640-7927

3 Bedroom Downtown Chicago Penthouse

Bedrooms 3
Space 2,500 sq. ft.
Property type apartment
Minimum Stay 3 nights


About the property

3 Bedroom, 2 Bathroom Condo

This is a beautiful 2,500 sq. ft penthouse loft in the heart of downtown Chicago.

The building is next to "Magnificent Mile" and steps away from amazing restaurants, comedy club (Zannies, Second City), theaters, boutique shopping, public transportation (red line, and 156 bus line), bars and just four blocks from the beach.

This building is truly one of a kind. Built in 1897 and completely renovated in 2016 this unit has exposed brick, 20 foot ceilings and 120 year old barn wood floors capped off with a rooftop deck overlooking Willis (Sears) Tower.

3 bedrooms all with king beds

2 full bathrooms

Full kitchen and living room

Master bedroom- Fit for a king. Located on balcony level overlooking living room. Vintage french doors open to balcony. Furnished with a tempurpedic king sized bed and 50 inch TV. Attached to marble bathroom with jacuzzi and all-marble rain forest dual shower head steam shower. Enjoy Kohler faucets and heated floors. (All assortments of toiletries, blow dryer, extra towels, linens, and extra pillows and blankets included)

Second and third bedrooms - Spacious and comfortable, both with king beds. Crown molding, large closets and spectacular views of Sears tower.

Second Bathroom- Marble floors, classics European style and granite counter tops. (All assortments of toiletries, blow dryer, extra towels and linens included)

Extra amenities include a push button fireplace, vintage 1950 first coin operated Valley pool table, dartboard, surround sound stereo system, PS3 (with movies and games), blu ray, board games and a 60-inch hanging TV equipped with HBO, Netflix, Showtime, TiVo, and Amazon.

Full laundry room in unit with iron and ironing board.

Last but not least is the rooftop deck. This view is absolutely magnificent. Your first walk out onto this large spacious rooftop deck will leave you speechless. It boosts a comfortable couch, grill, and large table all adorned with round draping bulb lights going from corner to corner of the deck, with a great view of the Chicago skyline.

You will never forget your Chicago visit when you are on the roof deck after the sunsets and the city lights fill up the sky.

Spoil yourself in the Windy City. There is nothing else like this in the city.

Upon arrival, a welcome packet that will explain to you all about the features of the penthouse and how to maximize your time while staying here. Anything from how to work the jacuzzi to how to operate the electronics is outlined and at your disposal when you walk in the door.

More Details
Registration Number : APPLICATION PENDING

Casey Shteamer
Member since: 2013
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
February 15, 2018


Old Town Apartment Accommodation and Amenities

Property Type:
  • apartment
  • floor 3
Building Type:
  • building
  • Guests provide their own meals
Floor Area:
  • 2500 sq. ft.
House Rules:
  • Check-in: 3:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 12
  • Max. adults: 12
  • Min. age of primary renter: 21
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
Location Type:
  • Downtown
  • Family
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer
  • Fireplace
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • 2 Bathrooms
  • Bathroom 1 - toilet , shower , jetted tub
    Bathroom 2 - toilet , combination tub/shower , shower
  • 3 Bedrooms, Sleeps 12
  • Bedroom 1 - 1 king
    Bedroom 3 - 1 king
    Bedroom 2 - 1 king
  • The master has a couch which can be used as an extra sleeping area.
  • Books
  • DVD Player
  • Game Room ...
  • Games
  • Music Library
  • Pool Table
  • Satellite / Cable
  • Stereo
  • Television ...
  • Video Games
  • Video Library
  • Deck / Patio
  • Outdoor Grill
  • Long-term Renters Welcome
  • wheelchair inaccessible ...
  • autumn foliage
  • botanical garden
  • churches
  • cinemas
  • festivals
  • library
  • live theater
  • marina
  • museums
  • playground
  • recreation center
  • restaurants
  • synagogues
  • zoo
Leisure Activities:
  • antiquing
  • paddle boating
  • photography
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • roller blading
  • sailing
**NO EXCESSIVE LOUD PARTIES. Quiet hours are 9pm-7am on weeknights and 11:00pm-7am on weekends (the building will fine, noise ordinance fines are $250 for the first occurrence and charges will be passed on to the guest) **


Excellent! 4.7/5 -
(15 traveler reviews)

73% Complete
26% Complete
0% Complete
0% Complete
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3 Bedroom Downtown Chicago Penthouse
average rating of 4.733333 based on 15 reviews

Awesome loft in a great Chicago neighborhood

  • 5 of 5

8 of us stayed in this incredibly beautiful, modern and spacious penthouse for the Chicago Marathon weekend. The house was equipped with everything we needed, 3 large and comfortable king beds, washer/dryer, fully stocked kitchen, etc. Note that there is no elevator - only stairs - so if you are traveling with a lot of stuff/heavy things or if you have mobility issues, getting in and out will be challenging. The street (North Wells) has everything you needs - a variety of restaurants, fantastic grocery stores, a liquor store, coffee shops and very close to the red train line.

Only "negative" comments would be that the street is quite loud at night which makes it a bit challenging to sleep - traffic, sirens, people - all kept us up each night. The blinds are also quite thin, so a lot of light gets let in, even at night from the street lights.

Highly recommended!

  • Submitted: Oct 9, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
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2 0

Chicago Family vacation

  • 4 of 5

We loved the ability to have all the family in one place! Great location. The kids loved the pool table.The only thing we had difficulties with was the outside door locking it was sticking.

  • Submitted: May 7, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
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0 0
Seattle, WA, USA

Chicago in Style

  • 5 of 5

Stayed with a group of close friends for a long weekend in Chicago. This Penthouse loft had all the amenities that we could ever ask for. We loved the exposed brick and the twenty foot ceilings in the living room. This loft is something we will try to stay at again when we come back to the Windy City.

  • Submitted: Mar 22, 2017
  • Stayed: March 2017
  • Source: VRBO, from HomeAway
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Baraboo, WI

Perfect location, beautiful space.

  • 5 of 5

This penthouse is wonderful--- so easy to live in, with no fussy details. The location is perfect, within walking distance of anything we wanted. If we were going further, we never waited longer than a couple of minutes for a cab. There were only a couple of glitches--- the pilot lights were out on the fireplace and the stove, maybe due to the construction going on in the lower apartment? A fire would have been nice, and we were counting on being able to cook. (We called about this, but no one ever showed up.) Also, we tried to use the oven, and it was so greasy that black smoke billowed out when we opened the door. You may want a new cleaning crew! The steps are killers--- but I realize that's on me, not you. However, that should be stressed in your description of the place. Thank goodness we were forewarned by previous reviews. Overall, we loved it.

  • Submitted: Nov 3, 2016
  • Stayed: October 2016
  • Source: VRBO, from HomeAway
Owner's Response: Hi Julie, I am so sorry about the pilot light. I had this looked into and it is back on. Thank you for the heads up as well as on the oven. I have asked the cleaning crew to pay special attention. Glad you enjoyed your stay! Best, Casey
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0 0

Great vacation rental

  • 4 of 5

The apartment was just as it was pictured and was plenty roomy for our family of five to relax and hang out together. The location was good with lots of food choices close by. The rating of four instead of five is due to the incredibly noisy air conditioning unit as well as the fact that Division St has plenty of fire trucks and ambulances going by. If you aren't sensitive to noise, then these two thimgs wouldn't matter at all. Also as previously mentioned in reviews, the two flights of stairs to reach the apartment are not for anyone with mobility issues. Overall it was a super-cool apartment and we would definitely recommend it.

  • Submitted: Aug 19, 2016
  • Stayed: August 2016
  • Source: VRBO, from HomeAway
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Broken Arrow OK

Nice property at a great location

  • 5 of 5

My family stayed here and truly enjoyed our visit. The property was clean, had good beds, and lots of space for time together. The location is great, convenient access to the CTA, a grocery store, restaurants, attractions. Check-in was easy. We would gladly stay here again.

Thank you for a wonderful experience.

  • Submitted: Jun 29, 2016
  • Stayed: June 2016
  • Source: HomeAway
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Nearest Airport
12 Miles
O'Hare and Midway and both easily accessible
Nearest Barpub
Next door, House of Glunz
Nearest Train
0.2 Miles
Red line El train
Nearest Restaurant
Next door, House of Glunz
Nearest Beach
1.1 Miles
North Ave Beach and Oak Street Beach
Car: not necessary

The penthouse is located in the heart of Old Town in Chicago in downtown.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $200
Damage Deposit $750

Owner's Cancellation Policy

  • 50% refund if canceled at least 30 days before arrival date.
  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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