Let’s be honest, hotels with upstairs and downstairs in Chicago can offer you the best possibilities to work and be entertained in one area of the apartment, and then totally relax and unwind in another. In this article, our team has researched and identified all the best options available in Chicago.
Also, we made sure to find duplexes that are located downtown or very close to it, giving you the possibility to be in the heart of the action in just a few minutes.
We loved all these suites, especially for their updated and elegant decor, but also because they come with excellent amenities, such as fitness centers, swimming pools, and in some cases, also a basketball court.
All of the options described below can be booked directly through our links via Booking.com.
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1. The Penthouse at the Freehand Hotel in Chicago
- This is a two bedroom, two bathroom duplex with a living room that is 904 square feet and offers beautiful city views and air conditioning to keep you cool on the hottest days
- The master bedroom has a large double bed, while a second room has four single twin beds, which can accommodate a total of 6 people
- This gorgeous penthouse suite features high ceilings with a sofa, a washer and dryer, as well as a mix of elegant hardwood and tile/marble floor
What Others are Saying
- The staff is very friendly and the location of the hotel is the best to visit all the sights around Chicago
- It is easily possible to reach the subway station and restaurants, all within walking distance
Make sure to choose the option called “Penthouse” to get this room with an upstairs and downstairs on Booking.com:
2. Luxury Penthouse Duplex with Personal Rooftop in Downtown Chicago
- This property offers two types of apartments with upstairs and downstairs in Chicago – one is the Penthouse and the other is the Duplex
- Both options offer a chic and modern decor
- They can accommodate up to 8 people in their massive 2,300 square foot layout, which comes with a spacious living room, a fully equipped kitchen, air conditioning, 2 bathrooms, and 3 bedrooms
- It is possible to park on the premises at an extra cost of $20 per day
What Others are Saying
- The location is excellent for short or longer stays, and there is no need to use a car to visit the city
- The property is very clean and the staff is very friendly
3. The Penthouse at Grand Plaza
- Each penthouse suite at the Grand Plaza in Chicago features two or more bedrooms, private balconies overlooking downtown and Lake Michigan, fully equipped kitchens, spacious dining areas, and a washer and dryer for your comfort
- You will get access to all the amenities the hotel provides, which include an outdoor pool, a fitness studio, a running track, and a basketball court
- Located in the central part of Downtown Chicago, with countless restaurants, shops, and entertainment just steps away
What Others are Saying
- People who have visited and returned several times to Grand Plaza comment on how clean all the apartments are
- Customer service is routinely praised as being excellent
- The large, floor-to-ceiling windows provide an amazing view over the city and the lake
- The kitchen is equipped and fully stocked, but there is also an on-site grocery store that is very convenient
4. Spacious Duplex with Free Parking in Uptown Chicago
- This is a two-story apartment located in the Logan Square neighborhood of Chicago with easy access to a subway station
- The spacious duplex comes with four bedrooms and three bathrooms, a fully equipped kitchen, and a free parking space on the premises
- The uptown neighborhood where this duplex is located offers easy access to many restaurants and shops
- Pets are also allowed in this duplex (for an additional fee)
- The apartment comes with air conditioning
- The host knows Chicago very well and she can provide you with recommendations of restaurants to try and museums to visit if this is your first time in the city
5. Bright Duplex in Wicker Park | 2BR + Patio Deck
- This is a bright and tastefully designed 2 bedroom and 3 bathroom duplex located in the Wicker Park district
- The kitchen is fully equipped, and there is also a microwave and dishwasher for your comfort. A washing machine is also available and is very is handy if you are planning a longer stay
- The beautiful outdoor patio is large and spacious, and there is the possibility to grill, too
What Others are Saying
Previous guests commented that the apartment is beautiful, well designed, and spacious, and everything you need is within 5 minutes
Summary - 5 Best Hotels with Upstairs and Downstairs in Chicago
We hope this list will help you secure the perfect duplex accommodation for your next trip to Chicago. They all offer a generous amount of space over 2 floors and many come with multiple bedrooms, a living room, and a kitchen area, making them perfect for extended stays or vacations with big groups.
It wasn’t very easy to find many options, so we think that these are the best hotels with upstairs and downstairs in Chicago.