5 Best Vrbo Vacation Accommodations In Chicago's Magnificent Mile - Updated 2024

Chronis
Chronis 
Updated
| 3 min read

When you visit the Windy City, Chicago, there are many areas that you can choose to stay in. One of the most unique ones is the Magnificent Mile, an upscale section of the city, in the centre of the shopping section and next to the Gold Coast, offering many attractions and things to do at night. In this area, you may find luxurious and high-end accommodations, suitable for both tourists or professionals staying for a few weeks or even a couple of months. We did a thorough search and offer you this list of the best Vrbo accommodations in Chicago’s Magnificent Mile.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 08, 2024.

1. Luxurious penthouse with a view (from USD 375)

Have a luxury getaway in Magnificent Mile, Chicago, in this 52nd-floor penthouse. The property boasts floor-to-ceiling windows in the living room that overlooks the city. You can even keep warm in front of the indoor fireplace while looking out to the city’s vibrant lights at night or while watching a movie on TV. You will also have access to shared amenities such as a gorgeous rooftop pool with plenty of loungers and an outdoor grill area. The building also features a shared sauna.

Stayed at this property?
Chicago, Illinois, United States
Wheelchair accessible Visual Aid: Braille
Apart-hotel 4 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Amenities & Room:
the view from our room was amazing
nice comfortable bed and couch
beautiful views well furnished comfortable apartment 500 feet above the streets of chicago
but it’s real value is it’s outstanding skyline views while relaxing in a very comfortable environment
nice location amazing views and wonderful gym facility - a++
Cleanliness:
super clean and comfortable
it was very clean and what the listing described
the apartment is very clean and chic
we had a great time during our stay in this clean & modern penthouse
clean with great views
Host:
owners communicate expectations & procedures clearly
doorman/staff is friendly and helpful
building staff is also very friendly
the owners were fantastic to work with
jim and jeri were responsive to any questions we had and there if you needed anything
Location:
great location to be near everything
this condo is in an awesome location
great location near shopping and restaurants
great and convenient location right in the heart of downtown
it's in a great downtown location
Read more reviews
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2. The Guild #2 (from USD 441)

This pet-friendly Vrbo near Magnificent Mile, Chicago, accommodates you and your furbaby’s dreams. It is seconds walk from Lake Michigan and Magnificent Mile. Restaurants such as The Signature Lounge at the 96th and Water Tower Place, a huge mall, are also within walking distance. While the outdoors offers a lot, staying inside is no hardship with the luxurious interior and convenient amenities. If you prefer staying inside, the fully equipped kitchen is at your service, and you can find entertainment on TV or the web.

Stayed at this property?
Chicago, Illinois, United States
Wheelchair accessible Visual Aid: Braille
condo 7 Guests 2 Bedrooms 2 Bathrooms

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3. Luxurious high-end condo in the center of the Magnificent Mile (from USD 190)

This luxurious Vrbo in Chicago downtown is situated on the 51st floor of a skyscraper, giving you a unique view of Lake Michigan and the rest of the city of Chicago. Right in the heart of the Magnificent Mile, this apartment is in a perfect location for a quick vacation or even a short-term housing option. The apartment has two bedrooms with a walk-in closet, a high-end kitchen with granite and big king-size beds. The property offers you amenities such as a swimming pool and a sundeck with a barbecue area, plus an exercise room. It’s an excellent choice for a luxurious getaway.

Stayed at this property?
8 reviews   Wifi Available
condo 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 29
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the kitchen was well appointed
The condo is amazing and looks just like the photos Thanks for an exceptional experience
If you are looking for wonderful views
We have already referred Chris and Jim to our friends who will be visiting Chicago in the future
We were wow'd by the condo and the views from the moment we walked in
Host:
helpful and gracious owner/host
The hosts Chris & Jim are a delightful couple and couldn't be nicer to us
Very well maintained clean and well stocked with nice high quality towels
Chris and Jim were the best hosts When we first checked in-
They were quick and responsive whenever we had a question about the condo or the city
Location:
Beautiful condo in the best location
Amazing views from an Amazing location Very well kept and
great location and easy access to everything
It is located within walking distance of anything you might need or want to do as well as the Red line right around the corner
Read more reviews
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4. Plush penthouse for an extravagant holiday (from USD 188)

The location of this apartment for short-term rent is great, with a fantastic view of the city’s skyline and right in the middle of the city’s everyday life. The apartment is really spacious, with comfortable bedrooms and a huge living area. The hosts are super friendly and provide all information about the nearby options. Ideal for four people, this is an excellent choice for a professional visiting the city for a few weeks or a family on a long vacation.

Stayed at this property?
Chicago, Illinois, United States
condo 5 Guests 2 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
The condo was everything we expected and more - great location - walkable to most things
The living area and master bedroom were much more spacious than we had expected
The bedrooms bathrooms and living area were large and very comfortable especially those breathtaking views on the 51st floor All the basic necessities were there for our use with the highest qual...
every detail was thought of to make it feel like it was home
The first thing that needs to be said for this condo is that the pictures really don't do it justice
Cleanliness:
and we were extremely pleased
Thank you Chris for sharing your beautiful and comfortable home
The owners take wonderful care of the unit and make sure it is in pristine condition for your arrival
Host:
Chris and Jim were extremely accommodating as hosts/owners and always responded quickly to our questions
The owners were extremely receptive to any questions we had and even made a very long drive to town to help us with the remote for the television
We really appreciated the care and consideration they displayed
They also are very quick to help you with any issue you may have
This was the most wonderful experience
Location:
It is in a great location with everything within walking distance
It is also convenient to everyday life needs such as drug stores grocery stores and salons
Grocery drug stores etc are two blocks away Easy walking to all the great world class restaurants on Rush Street and Michigan Ave
It would be extremely difficult to imagine a better location - 2 blocks west of Michigan Avenue so great dining entertainment and the beach are all an easy walk but the surrounding streets were ...
nothing is ever a problem
Read more reviews
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5. Exquisite penthouse near so many attractions (from USD 946)

Prepare for the ultimate city living in this three-bedroom penthouse. Exquisitely decorated and designed, this rental showcases beautiful views of Lake Michigan and Chicago from its 20-ft floor-to-ceiling windows. The addition of amenities like a fireplace, an oversized balcony, a fully equipped kitchen, and so much more make for a luxurious vacation in this rental. The cherry on top when staying in this penthouse is that it’s located less than 1 mile (1.6 kilometers) from Chicago Riverwalk, John Hancock Center, State Street, and other iconic attractions.

Stayed at this property?
240 reviews   Wifi Available
hotel suites 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
because there are only three bedrooms 4
because that will minimize the risk that you'll make marks on the staircase walls with your luggage
The online photos looked great and the reviews were glowing
luggage upstairs to the 56th floor bedrooms; instead you need to exit with your luggage wait for the elevator take it up one floor
Very spacious Kitchen is fully equipped
Cleanliness:
Very clean comfortable accommodations
The condo is very clean and well equipped
Very clean and well supplied
Host:
The communication with the owner is very thorough and in timely manner
know that your rental rate does NOT include an amenity you would expect in any good hotel or well appointed home
they had terrible experiences with other vistors and thats why they have a super-strict and demanding tone of voice
The most amazing things about this property are the views
and even when Jim came the next day to untangle them sufficiently to let the blinds down most of the way the vents did not close completely and there were light leaks everywhere
Location:
It is also a very convenient location
The property is ideally located in downtown next to red line walking distance from The Magnificent Mile and lots of attractions
And so much else was within walking distance
The location in the River North area is fantastic and many top ranked restaurants are within walking distance
And the location is amazing
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

Just magnificent

This upscale area of Chicago is the place to be when you visit the city. With options for everyone, such as couples having a long weekend, families visiting the museums, or even professionals staying in the city on business, this area offers many memorable things to do. So keep our list, find the most suitable option for you, and live like a local in downtown Chicago.

Frequently asked questions about Vrbo vacation accommodations in Chicago's Magnificent Mile


Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Hello ! I'm Chronis and I'm currently living in Athens, Greece. I love to travel and I would love to share my experience with you.

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