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Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992

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 full 360 degree 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

Casey Shteamer
Member since: 2013
Speaks English
Response time:
Within a few hours
Response rate:
Calendar last updated:
14 March, 2017


Accommodation and facilities for this holiday apartment in Old Town in Chicago

Property Type:
  • apartment
  • floor 3
Building Type:
  • building
  • Self-catering
Floor Area:
  • 2500 sq. ft.
House Rules:
  • Max. occupancy: 8
  • non smoking only
  • children welcome
Location Type:
  • city centre ...
  • 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
  • Hob
  • Toaster
  • Dining Area
  • 2 Bathrooms
  • Bathroom 1 - Toilet , Shower Enclosure , Jacuzzi
    Bathroom 2 - Toilet , Bath with Shower , Shower Enclosure
  • 3 Bedrooms, Sleeps 8
  • Bedroom 1 - 1 Extra Lg. Double Bed
    Bedroom 3 - 1 Extra Lg. Double Bed
    Bedroom 2 - 1 Extra Lg. Double Bed
  • Books
  • DVD Player
  • Game Room ...
  • Games
  • Music Library
  • Pool Table
  • Satellite / Cable
  • Stereo
  • Television ...
  • Video Games
  • Video Library
  • Terrace
  • Barbecue
  • Long-term Renters Welcome
  • wheelchair inaccessible ...
  • autumn foliage
  • botanical garden
  • churches
  • cinemas
  • festivals
  • library
  • live theatre
  • marina
  • museums
  • playground
  • recreation centre
  • restaurants
  • synagogues
  • zoo
Leisure Activities:
  • antique hunting
  • 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) **


Wonderful! 4.8/5 -
(13 traveller reviews)

3 Bedroom Downtown Chicago Penthouse
average rating of 4.769231 based on 13 reviews
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.

  • Review Submitted: Mar 22, 2017
  • Date of Stay: Mar 2017
  • Source: VRBO, from HomeAway
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0 0
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.

  • Review Submitted: Nov 3, 2016
  • Date of Stay: Oct 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.

  • Review Submitted: Aug 19, 2016
  • Date of Stay: Aug 2016
  • Source: VRBO, from HomeAway
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0 0
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.

  • Review Submitted: Jun 29, 2016
  • Date of Stay: Jun 2016
  • Source: HomeAway
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0 0

Big city loft does not disappoint!

  • 5 of 5

Outstanding! What a lovely city escape. I agree with the previous reviewers that a couple of floor lamps would have been nice.

  • Review Submitted: Dec 16, 2015
  • Date of Stay: Nov 2015
  • Source: HomeAway
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1 0

Amazing Place to Stay in Chicago

  • 5 of 5

First I loved how hidden from the street this Penthouse was located. A great surprise behind the green door!

The apt is the best, the decorating spot on (exposed bricks, pipes, high ceilings not to mention a pool table, dart boards, guitars to play and a roof garden) and at the same time totally comfortable. The apartment guide was so informative and mostl important so friendly. They made everything easy on the vacationer. Our trip will be one of my favorites ever and much of it was based on these wonderful lodgings. Thanks so much!

  • Review Submitted: Nov 23, 2015
  • Date of Stay: Oct 2015
  • 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.


Prices & Availability

Prices for this holiday apartment in Old Town, Illinois

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
My Standard Rate
3 night minimum stay
for 3 nights

Additional pricing information

Refundable Damage Deposit £586.75
Cleaning Fee £156.47
Tax Rate 17.0%

Owner's Cancellation Policy

100% refund for cancellations more than 60 days before check-in date.

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Partner Offers

Portable wifi hotspot

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