Apartment

55th Floor Penthouse with Award-Winning Views

Photo gallery for 55th Floor Penthouse with Award-Winning Views

2 story great room with gas fireplace and wrap around balcony and queen sleeper sofa.
Rooftop pool on the 9th floor
Primary king bedroom with ensuite bath
State of the art Fitness Center
Dining with world class view!

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
3 bedrooms2 bathroomsSleeps 82200 sq ft

Popular amenities

  • Indoor pool
  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Outdoor barbecue

Explore the area

View in a map
Chicago, IL
  • Place, Michigan Avenue
    ‪5 min walk‬
  • Place, Chicago Riverwalk
    ‪6 min walk‬
  • Place, Millennium Park
    ‪11 min walk‬
  • Airport, Chicago, IL (ORD-O'Hare Intl.)
    ‪24 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Living Room 1

1 Double Sofa Bed

2 bathrooms

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Spaces

Kitchen
Office
Balcony

About this property

55th Floor Penthouse with Award-Winning Views

Summary:

Experience Chicago from a 55th-floor duplex penthouse in River North. This 3-bed, 2-bath residence sleeps 8 and features panoramic skyline and Lake Michigan views through dramatic two-story windows. Enjoy a gas fireplace, full kitchen, and a dedicated workspace with high-speed Wi-Fi, ideal for remote work with an unmatched backdrop.



Perfect for families, groups, or business travelers seeking luxury and convenience, just steps from Michigan Ave, the Riverwalk, and Millennium Park.



The Space:

Perched 55 stories above the city, this stunning 3-bedroom, 2-bathroom duplex penthouse offers an unforgettable Chicago experience. The dramatic two-story living room, features floor-to-ceiling windows that flood the space with natural light and provide breathtaking panoramic views of the skyline and Lake Michigan.



In the evenings, relax by the cozy gas fireplace and watch the city lights sparkle. With space to comfortably sleep 8 guests, this is the pinnacle of city living.



Sleeping Arrangements:

Primary Bedroom: King bed with a full en-suite bathroom.

Second Bedroom: Queen bed.

Third Bedroom: Queen bed.

Living Room: Queen sleeper sofa for additional guests.



In-Unit Amenities:

Fully equipped kitchen with stainless steel appliances

High-speed Wi-Fi

Smart TV

In-unit washer and dryer

Gas fireplace



Guest Access:

Guests will have private access to the entire 3-bedroom duplex penthouse.



Additionally, you'll have full access to Grand Plaza's resort-style shared amenities, including:

Outdoor swimming pool and sundeck

State-of-the-art fitness center

Indoor basketball court

Outdoor running track

Business center with dedicated workstations

Direct in-building access to a Jewel/Osco grocery store

24-hour door staff for security and assistance



The Neighborhood:

The Magnificent Mile is Chicago’s premier commercial district. The vibrant, bustling area is home to upscale shops, luxe fashion outlets, cool restaurants and posh hotels. Landmarks include the historic Chicago Water Tower, the neo-Gothic Tribune Tower, the terracotta Wrigley Building skyscraper and the 100-story John Hancock Center, which has a rooftop observation deck with fine dining and panoramic city views



Getting Around:

-Walk Score: 100 – steps from dining, shopping, and nightlife

-50 feet to the Red Line

-Near Magnificent Mile, Millennium Park, Riverwalk

-Surrounded by top restaurants, coffee shops, and boutiques

-CTA Bus Stops Nearby – Multiple lines within 1 block for access to neighborhoods like West Loop, Lincoln Park, and Hyde Park

-Uber, Lyft & Taxis – Abundant and easily accessible at all hours

-Divvy Bike Station – 1 block east



Other Things to Note:

Pre-arrival Requirements: For the security of our guests and the property, we require a government-issued photo ID and a complete guest list before check-in.

Children: Children are welcome. A pack-n-play is available upon request to make your travel easier.

Maintenance: On-call maintenance is available should you need any assistance during your stay.

Registration: City of Chicago Registration Number: 2210737



Interaction with Guests:

We respect our guests' privacy and offer a self-check-in process. While we won't be present during your stay, our team is available and on-call for any maintenance needs or questions to ensure you have a comfortable and seamless experience.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Air conditioning
Gym

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Government issued photo ID required prior to arrival. Guest list required prior to arrival Strict No Party policy Strict No Pet Policy Strict No Sm...

Important information

You need to know

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
This property accepts credit cards and cash
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Chicago

Located in Downtown Chicago, a neighbourhood in Chicago, this apartment is near theme parks and on a river. Chicago Theatre and Art Institute of Chicago are cultural highlights, and travellers looking to shop may want to visit Michigan Avenue and Navy Pier. Looking to enjoy an event or a game? See what's going on at Soldier Field or United Center. Discover the area's water adventures with nearby fishing, or enjoy the great outdoors with cycling.
Map
Chicago, IL

What's nearby

  • Michigan Avenue - 5 min walk - 0.4 km
  • Chicago Riverwalk - 6 min walk - 0.6 km
  • Northwestern Memorial Hospital - 8 min walk - 0.7 km
  • Chicago Theatre - 9 min walk - 0.8 km
  • Millennium Park - 11 min walk - 1.0 km

Getting around

  • Grand Station (Red Line) - 1 min walk
  • Millennium Station - 13 min walk
  • Chicago Midway Airport (MDW) - 40 min drive

Restaurants

  • ‪Eataly - ‬2 min walk
  • ‪Bally's Casino - ‬2 min walk
  • ‪Weber Grill Restaurant - ‬1 min walk
  • ‪Chipotle Mexican Grill - ‬1 min walk
  • ‪UNO Pizzeria & Grill - ‬2 min walk

Frequently asked questions

Does 55th Floor Penthouse with Award-Winning Views have a pool?

Yes, this property has a pool.

How much does it cost to stay at 55th Floor Penthouse with Award-Winning Views?

As of 12 Apr, 2026, prices found for a 1-night stay for 2 adults at 55th Floor Penthouse with Award-Winning Views on 18 Jun, 2026 start from S$1,717, 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.

Is 55th Floor Penthouse with Award-Winning Views pet-friendly?

No, pets are not allowed at this property.

How much is parking at 55th Floor Penthouse with Award-Winning Views?

On-site parking is available at the property.

What time is check-in at 55th Floor Penthouse with Award-Winning Views?

Check-in begins at 4:00 PM.

What time is check-out at 55th Floor Penthouse with Award-Winning Views?

Checkout is at 10:00 AM.

Where is 55th Floor Penthouse with Award-Winning Views located?

Located in Downtown Chicago, this apartment building is within a 5-minute walk of Bally's Casino Chicago and Michigan Avenue. Chicago Riverwalk and Chicago Theatre are also within 10 minutes. Grand Station (Red Line) is only a 2-minute walk and Chicago Station (Red Line) is 6 minutes.

Reviews

10

Exceptional

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. 290 out of 306 reviews
Rating 8 - Good. 13 out of 306 reviews
Rating 6 - Okay. 2 out of 306 reviews
Rating 4 - Poor. 1 out of 306 reviews
Rating 2 - Terrible. 0 out of 306 reviews

10/10

Cleanliness

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Suzanne H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great communication from the host and the place looks exactly like the picture! We enjoyed being right in the middle of the action with close walks to so many things in the city.
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

trailer147

Liked: Cleanliness, check-in, communication, location, listing accuracy
The views were unbelievable, the location is terrific, the condo is very clean and well-maintained, and the hosts were great.
Stayed 4 nights in Feb 2026
Response from VrboOwner on 10 Mar, 2026
Thank you for the great review! We’re glad you enjoyed the unbelievable views and found the condo clean and well maintained. A big shout-out to our cleaning crew of nearly 20 years who work hard to keep everything in great shape for our guests. The location really does make exploring Chicago easy — with a Walk Score of 100, the Red Line right on the corner, plenty of restaurants nearby, and the Jewel/Osco grocery store right in the building for added convenience. We appreciate the kind words about the hosting as well. Thank you for choosing The Penthouses at Grand Plaza, a collection of 11 penthouse residences in the building. We’d love to welcome you back for another stay and another true Penthouse experience. 🏙️
Verified

10/10 Excellent

William A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic view of the city and lake. Awesome apartment and very friendly staff. We booked on short notice and the host was very friendly and accommodating. We will definitely stay here again!
Stayed 4 nights in Feb 2026
Response from VrboOwner on 10 Mar, 2026
Thank you for the wonderful review! We’re glad you enjoyed the incredible views of the city and Lake Michigan — from that height it really is a special perspective of Chicago. It’s great to hear the apartment worked well for you, especially with a short-notice booking. We always try to make the process as smooth and accommodating as possible. And a big shout-out to our cleaning crew of nearly 20 years who help keep everything spotless and ready for guests. The location also makes it easy to explore — with a Walk Score of 100, the Red Line right on the corner, great restaurants nearby, and the Jewel/Osco grocery store right in the building. Thank you for choosing The Penthouses at Grand Plaza, a collection of 11 penthouse residences in the building. We look forward to welcoming you back for another stay and another true Penthouse experience. 🏙️
Verified

10/10 Excellent

Angela S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We stayed here for New Years Eve and had the best time. Close proximity- walking distance to Mag mile, river walk and all the great restaurants. So convenient with the grocery store down stairs. And the best part was the views of the city and the lake! So gorgeous. Would absolutely stay again.
Stayed 5 nights in Dec 2025
Response from VrboOwner on 24 Jan, 2026
Ringing in the New Year with sweeping city and lake views is pretty special, and we’re happy you were able to enjoy it. The location really does make it easy to explore everything on foot (Mag Mile, Riverwalk, restaurants), and having Jewel/Osco right in the building is definitely a plus for convenience. We truly appreciate you choosing The Penthouses at Grand Plaza and would love to welcome you back anytime for another true Penthouse experience.
Verified

10/10 Excellent

Carrie P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The views are majestic.
Stayed 4 nights in Oct 2025
Response from VrboOwner on 25 Nov, 2025
Thank you! Those high-floor views really are something special — we’re glad you enjoyed them. We’d love to welcome you back for another true Penthouse experience!
Verified

10/10 Excellent

Mark D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, great property, great views.
Balcony view
Stayed 6 nights in Aug 2025
Response from VrboOwner on 20 Sept, 2025
Thanks for the 10/10! We’re glad the location, property, and views all delivered—and that photo you shared is fantastic (the skyline really shows what makes this place special). Being in River North—Walk Score 100 with the Grand Red Line on the corner—makes exploring easy. We work hard to provide a true Penthouse experience and would love to host you again.
Verified

10/10 Excellent

Jessica O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful views and nice space to entertain in. The community benefits were also a bonus (billiards table, pool, dog park, gym)
Stayed 4 nights in Oct 2025
Response from VrboOwner on 25 Nov, 2025
Thanks so much for the great review! We’re glad you enjoyed the views and found the space comfortable for entertaining — that combination of high-floor scenery and open layout is hard to beat. It’s also great to hear you made use of the building amenities; the billiards room, pool deck, dog park, and gym are guest favorites. We’d love to welcome you back anytime for another true Penthouse experience!
Verified

10/10 Excellent

Donnie T.

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

Great Stay

Greta location, great stay, perfect location to so many things and if not subway at building for easy travel.
Stayed 4 nights in Mar 2025
Response from VrboOwner on 26 Apr, 2025
Thanks so much for the great review! I’m glad you enjoyed the stay and that the location made getting around the city so easy. Would love to host you again anytime you’re back in Chicago! 🙌🌆
Verified

10/10 Excellent

Gert H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location is fantastic and then there is the view ... spectacular!!! You lie in the bed and watch the night skyline of Chicago, unbeatable.
Stayed 4 nights in Aug 2025
Response from VrboOwner on 20 Sept, 2025
Thank you for the 10/10! Delighted the location and those spectacular skyline views—even from bed—made the stay. Being in River North with a Walk Score of 100 and the Red Line (Grand) on the corner makes everything easy, and the night view is hard to beat. We aim to deliver a true Penthouse experience and would love to host you again.
Verified

10/10 Excellent

Torrey Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great rental! The property was perfectly located and the views are unparalleled. Jim and Jeri-Lou were very responsive and helpful. I will 100% stay here again on my next trip to Chicago.
Stayed 5 nights in Jul 2025
Response from VrboOwner on 20 Sept, 2025
Thank you for the 10/10! We’re thrilled the location and unparalleled views made the trip—and appreciate the shout-out on responsiveness. With a Walk Score of 100 and the Red Line (Grand) on the corner, it’s easy to make the most of Chicago right from the building. We aim to deliver a true Penthouse experience every stay and would love to host you again on your next visit.
Verified

10/10 Excellent

Elizabeth F.

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

Great stay

Lots of space, incredible view, easy access to restaurants and shopping. Pool and gym area a plus.
Stayed 5 nights in Jun 2024
Response from VrboOwner on 4 Aug, 2024
Thanks, Elizabeth, for your visit. Wonderful to hear that you had a Great stay. We do hope to see you back soon.
Verified

10/10 Excellent

Dan E.

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

Chicago stay

Great week, enjoyed the stay.
Stayed 5 nights in Jul 2023
Response from VrboOwner on 17 Sept, 2023
Dan, thank you for your stay and all we need to hear is that you had a great week and enjoyed your stay. Hope to see you back again.
Verified

10/10 Excellent

Kristine S.

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

Piece of Heaven

Place was amazing and we loved being able to sit around the fire with the city as our backdrop
Stayed 3 nights in Feb 2025
Response from VrboOwner on 26 Apr, 2025
Thank you so much! I’m really glad you enjoyed the space — there’s nothing quite like sitting by the fire with the city skyline all around you. Would love to host you again anytime you're back in Chicago! 🔥🌆🙌
Verified

10/10 Excellent

Cleita H.

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

Girls Weekend

Location was perfect for 4 high school girlfriends annual get together. We loved the fireplace in the 2-story living room as it was very cold the week-end we were there. We had a blast.
Stayed 3 nights in May 2025
Response from VrboOwner on 20 Sept, 2025
Thank you for the 10/10 and the lovely “Girls Weekend” note! We’re thrilled the two-story living room with the fireplace made those chilly days cozy and fun. The River North location is perfect for an annual meetup—Walk Score 100 with the Red Line (Grand) on the corner—so it’s easy to get everywhere together. We aim to deliver a true Penthouse experience for trips just like this and would love to host the four of you again next year.
Verified

10/10 Excellent

Dr. Angela Marie S.

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

The View!

We loved our stay in Chicago! The grocery store near the entrance of the building had everything we needed. Also there were plenty of great restaurants nearby to eat at. The view was stunning during the day but breathtaking at night. Definitely worth every penny!
Stayed 4 nights in Jun 2025
Response from VrboOwner on 20 Sept, 2025
Thank you for the 10/10 and “The View!” shout-out! We’re thrilled the skyline delivered—stunning by day and breathtaking at night—and that the neighborhood made things easy. Having Jewel-Osco right in the building plus countless restaurants nearby (River North Walk Score 100, Red Line—Grand—on the corner) is a big part of the experience. We aim to deliver a true Penthouse stay every time and are glad it felt worth every penny. We’d love to host you again!
Verified

10/10 Excellent

Graham W.

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

Beautiful property

Jim does a great job of communicating with us. The property is truly a gem!
Stayed 5 nights in Mar 2025
Response from VrboOwner on 26 Apr, 2025
Thank you so much! I’m really glad the communication and the property made your stay a great one. Would love to host you again anytime you’re back in Chicago! 🙌🌆
Verified

10/10 Excellent

Jessica K.

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

Great high rise!

My family had a blast staying in this beautiful property. Great location, easy to get to many attractions, and amenities were great.
Stayed 4 nights in Jul 2022
Response from VrboOwner on 15 Aug, 2022
Jessica thank you for your business. So happy we could be a part of your family memories. With a walk score of 100, the location is the very best in the city.
Verified

10/10 Excellent

Robert S.

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

Great location wonderful view

If you are looking for an amazing view of Chicago in a place that has everything you need during your stay; this is the place for you!
Stayed 4 nights in Dec 2020
Response from VrboOwner on 31 Dec, 2020
Robert, thank you for your business. We are so happy you enjoyed your stay. hope to see you again soon.
Verified

10/10 Excellent

Karen R.

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

Great place to visit

The location of the property was perfect. Easy to walk to many locations. The condo was comfortable and had a beautiful view of the city.
Stayed 6 nights in Sep 2023
Response from VrboOwner on 16 Oct, 2023
Karen thank you for your visit. So happy to hear that you enjoyed your stay. With a walk score of 100 the location really does not get much better. Oh, by the way this unit has won awards for the ‘Best City View’ in the World. We look forward to your return.
Verified

10/10 Excellent

Anthony D.

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

Penthouse Views

Amazing views, clean, good for a family, great location. Would recommend and stay again.
Stayed 4 nights in Nov 2023
Response from VrboOwner on 20 Dec, 2023
Thank you Anthony for your visit. We do hope to see you back again.
Verified

10/10 Excellent

Aaron W.

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

Amazing Penthouse

This place is incredible. I wish we could stay forever. The view never gets old, and it looks even better at night.
Stayed 3 nights in Jan 2025
Response from VrboOwner on 26 Feb, 2025
Aaron, Thank you so much for your kind words! We’re so happy you loved your stay and the amazing views—especially at night, they really are something special! This unit has actually won awards for the "Best City View in the World," and we love sharing that experience with our guests. We work really hard to create a true Penthouse experience and it means a lot to hear you enjoyed it. We’d love to have you back anytime—stay forever if you could!
Verified

10/10 Excellent

Coreen R.

Long weekend with family, The apartment was beautiful, very spacious amazing views.

The location was great, The owners were very personable and accommodating. We had everything we needed and more!
Stayed 4 nights in Jan 2019
Response from VrboOwner on 29 Mar, 2020
Coreen We do try and make sure that you will have most everything you will need. Not only bath products (body wash, shampoo and conditioner) but in the kitchen as well. Hope to see you back real soon!
Verified

10/10 Excellent

Rosa C.

We loved our stay in the penthouse..would definitely rent it again!

We had a nice romantic weekend.
Stayed 3 nights in Feb 2019
Response from VrboOwner on 29 Mar, 2020
Thanks for your visit.
Verified

10/10 Excellent

Eileen W.

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

Fabulous accommodations!

This pent house was even better than the pics show!!! Unbelievable view and the location is great!!!! Would book again if in Chicago and recommend to all.
Stayed 3 nights in Aug 2024
Response from VrboOwner on 8 Sept, 2024
Thank you for the fantastic review! We're thrilled to hear that the penthouse exceeded your expectations—those views never get old, do they? 🌆 We’re so glad you enjoyed your stay and appreciate your recommendation. Looking forward to welcoming you back on your next trip to Chicago!
Verified

10/10 Excellent

Christina S.

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

Amazing location and apartment

We had an amazing long weekend in Chicago! This place is amazing and we could not get over the views! The home was very clean and equipped with everything we needed. We would stay here again! Close to everything and lots within walking distance.
Stayed 4 nights in Nov 2024
Response from VrboOwner on 23 Dec, 2024
Thanks, Christina, for your visit and review. This unit has won awards for the 'Best City View in the World'. We do hope to see you back again.

About the host

Hosted by Owner/Manager

Host profile image

Why they chose this property

In Real Estate they say 'location, location, location'. We have that. What we say is 'views, views, views'.

What makes this property unique

Few cities have building as tall as Chicago, fewer still have rent-able Penthouse units. This is your opportunity to experience luxury living at it's finest.

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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