Entire apartment

Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

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A modern bedroom with a large bed, a small side table, a coffee table, and a view of the city through large windows.
A deck with a table and an umbrella, a barbecue grill, and a view of buildings in the background.
A bathroom with white subway tiles, a toilet, a shower area, and a vanity with a mirror.
A rooftop terrace with a fire pit, seating area, and a city skyline view.
A rooftop patio with a wooden table and chairs, a grill, and a view of a city skyline.

Reviews

10 out of 10
Exceptional

Entire apartment

2 bedrooms2 bathrooms60 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space
  • Parking available

Explore the area

View in a map
Chicago, IL
  • Place, Milwaukee Avenue
    ‪3 min walk‬
  • Place, Intuit: The Center for Intuitive and Outsider Art
    ‪8 min walk‬
  • Place, The Salt Shed
    ‪19 min walk‬
  • Airport, Chicago, IL (ORD-O'Hare Intl.)
    ‪31 min drive‬

Room options

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About this property

Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

Step into a sun-drenched, top-floor sanctuary with a private roof deck and sweeping skyline views. Whether you`re here for a work trip or a Chicago food tour, this classic Chicago walk-up offers a quiet escape above the city bustle.

The roof deck is accessed through an interior staircase inside the apartment. It is completely private and reserved for your use so you can take in the stunning Chicago skyline, lounge around the fire pit, or enjoy a fresh cooked meal with the grill and outdoor dining table.

The space comfortably sleeps six with a queen bed in each of the two bedrooms and a sofa bed in the living room. The sofa bed conveniently pulls out into a queen size bed and extra pillows and sheets are stocked in the closet.

The home features two full bathrooms: a communal guest bathroom with a standard-size soaking tub and a private en-suite bathroom in the second bedroom equipped with a modern shower stall.

Sleeping arrangements:
- Bedroom #1: queen size bed with en-suite bathroom
- Bedroom #2: queen size bed
- Living room: queen size sofa bed

Amenities:
Private roof deck accessed directly from the apartment, outdoor grill and fire pit, self check-in, high-speed Wifi, dedicated workspace, kitchen island with bar stool seating, smart TV with Airplay, and in-unit laundry

Location:
You’re perfectly positioned at the intersection of Chicago’s best vibes.
- All within walking distance: coffee shops, multiple parks, BYOB Mexican, Mediterranean, and Sushi, grocery & convenience stores, and countless bars & restaurants
- Short rides: less than 5 minutes from the trendy West Loop and Wicker Park neighborhoods, and less than 10 minutes from the United Center

Stress-Free Parking:
Rare for the city! We provide free daily street parking permits for up to two weeks, or enjoy free non-permit parking just a block away on Huron St.

Other things to note:
The apartment is on the 4th floor of a walk-up building which does not have an elevator.

Early check-in:
- Enjoy free early check-in for booking direct on flexhome.com
- Accommodations will be made for self check-in anytime after 1pm
- All requests are subject to availability

Requirements:
1. Agree to our House Rules
2. Verify your identity by uploading a government-issued ID and selfie through our ID verification partner
3. Pay a $200 refundable security deposit. Deposit is payable online only and refund is issued after check-out assuming no damage, missing items, or broken House Rules. Refunds take 5-10 business days to appear on your statement

House rules:
1. Ages 21+ to book.
2. Authorized guests only, and no booking on behalf of others.
3. No parties, gatherings, or commercial uses.
4. No smoking of any kind anywhere on the premises including outdoor spaces ($150 fine will be assessed and additional fees for remediation may apply).
5. Quiet time after 10pm.
6. Guests must cover the cost to replace unreturned access devices such as keys, key cards, fobs, or parking passes.
7. Rental agreement required for all stays of 28+ days, all direct bookings, and otherwise at our sole discretion.
8. Guests take full responsibility for loss, injury, or damages that occur on the premises and its facilities.
9. Bookings by local guests are prohibited at this property. Please contact us with any questions.
*Booking a reservation constitutes an agreement to comply with the House Rules. Guests who violate these rules are liable for any associated damages, fees, or expenses and may be removed from the property without refund.

#R26000139446
1. Ages 21+ to book.
2. Authorized guests only, and no booking on behalf of others.
3. No parties, gatherings, or commercial uses.
4. No smoking of any kind anywhere on the premises including outdoor spaces ($150 fine will be assessed and additional fees for remediation may apply).
5. Quiet time after 10pm.
6. Guests must cover the cost to replace unreturned access devices such as keys, key cards, fobs, or parking passes.
7. Rental agreement required for all stays of 28+ days, all direct bookings, and otherwise at our sole discretion.
8. Guests take full responsibility for loss, injury, or damages that occur on the premises and its facilities.
9. Bookings by local guests are prohibited at this property. Please contact us with any questions.
*Booking a reservation constitutes an agreement to comply with the House Rules. Guests who violate these rules are liable for any associated damages, fees, or expenses and may be removed from the property without refund.
During your stay at this apartment building, you're just a quick walk from Milwaukee Avenue. The apartment offers a kitchen and 2 bathrooms.
  • Air-conditioned apartment with kitchen, washing machine, and 2 bathrooms
  • Just a 3-minute drive from United Center and a few minutes from Michigan Avenue
This apartment offers its guests barbecue grills. The front desk is open around the clock.

This Chicago apartment is smoke free.


Property amenities

Internet

  • Available in the apartment: WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Books
  • TV

Outdoor areas

  • Barbecue grill
  • Firepit
  • Patio

Laundry

  • Washing machine

Work spaces

  • Desk
  • Desk chair
  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

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)
  • Fire extinguisher

General

  • Unit size: 646 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 21

Check-out

Check-out before 11:00 AM

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

Rules

1. Ages 21+ to book. 2. Authorized guests only, and no booking on behalf of others. 3. No parties, gatherings, or commercial uses. 4.

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.
Property Registration Number R26000139446
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

Property is also known as

504776

Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6 Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

10/10

Cleanliness

Reviews

Verified

10/10 Excellent

Jessica C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very happy with our stay. Loved the rooftop views! The host was very friendly and welcoming.
Stayed 1 night in May 2026
Verified

10/10 Excellent

William C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Good location for our stay in Chicago. The rooftop was great and a very comfortable stay.
Stayed 2 nights in Jun 2026
Verified

10/10 Excellent

Dennis R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Comfortable apartment and the rooftop deck was a great bonus. Street parking was convenient. Would absolutely stay again.
Stayed 2 nights in Apr 2026