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 October 26, 2025.
1. Luxurious penthouse with a view
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.
Chicago, Illinois, United States
Top guest reviews
Host:
owners communicate expectations & procedures clearlydoorman/staff is friendly and helpfulbuilding staff is also very friendlythe owners were fantastic to work withjim and jeri were responsive to any questions we had and there if you needed anythingLocation:
great location to be near everythingthis condo is in an awesome locationgreat location near shopping and restaurantsgreat and convenient location right in the heart of downtownit's in a great downtown locationCleanliness:
super clean and comfortableit was very clean and what the listing describedthe apartment is very clean and chicwe had a great time during our stay in this clean & modern penthouseclean with great viewsRead more reviewsAmenities & Room:
the view from our room was amazingnice comfortable bed and couchbeautiful views well furnished comfortable apartment 500 feet above the streets of chicagobut it’s real value is it’s outstanding skyline views while relaxing in a very comfortable environmentnice location amazing views and wonderful gym facility - a++
2. The Guild #2
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.
Chicago, Illinois, United States
3. Luxurious high-end condo in the center of the Magnificent Mile
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.
Chicago, Illinois, United States
Top guest reviews
Host:
helpful and gracious owner/hostThe hosts Chris & Jim are a delightful couple and couldn't be nicer to usVery well maintained clean and well stocked with nice high quality towelsChris 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 cityLocation:
Beautiful condo in the best locationAmazing views from an Amazing location Very well kept andgreat location and easy access to everythingIt is located within walking distance of anything you might need or want to do as well as the Red line right around the cornerRead more reviewsAmenities & Room:
the kitchen was well appointedThe condo is amazing and looks just like the photos Thanks for an exceptional experienceIf you are looking for wonderful viewsWe have already referred Chris and Jim to our friends who will be visiting Chicago in the futureWe were wow'd by the condo and the views from the moment we walked in
4. Plush penthouse for an extravagant holiday
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.
Chicago, Illinois, United States
Top guest reviews
Host:
Chris and Jim were extremely accommodating as hosts/owners and always responded quickly to our questionsThe 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 televisionWe really appreciated the care and consideration they displayedThey also are very quick to help you with any issue you may haveThis was the most wonderful experienceLocation:
It is in a great location with everything within walking distanceIt is also convenient to everyday life needs such as drug stores grocery stores and salonsGrocery drug stores etc are two blocks away Easy walking to all the great world class restaurants on Rush Street and Michigan AveIt 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 problemCleanliness:
and we were extremely pleasedThank you Chris for sharing your beautiful and comfortable homeThe owners take wonderful care of the unit and make sure it is in pristine condition for your arrivalRead more reviewsAmenities & Room:
The condo was everything we expected and more - great location - walkable to most thingsThe living area and master bedroom were much more spacious than we had expectedThe 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 homeThe first thing that needs to be said for this condo is that the pictures really don't do it justice
5. Exquisite penthouse near so many attractions
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.
Chicago, Illinois, United States
Top guest reviews
Host:
The communication with the owner is very thorough and in timely mannerknow that your rental rate does NOT include an amenity you would expect in any good hotel or well appointed homethey had terrible experiences with other vistors and thats why they have a super-strict and demanding tone of voiceThe most amazing things about this property are the viewsand 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 everywhereLocation:
It is also a very convenient locationThe property is ideally located in downtown next to red line walking distance from The Magnificent Mile and lots of attractionsAnd so much else was within walking distanceThe location in the River North area is fantastic and many top ranked restaurants are within walking distanceAnd the location is amazingCleanliness:
Very clean comfortable accommodationsThe condo is very clean and well equippedVery clean and well suppliedRead more reviewsAmenities & Room:
because there are only three bedrooms 4because that will minimize the risk that you'll make marks on the staircase walls with your luggageThe online photos looked great and the reviews were glowingluggage upstairs to the 56th floor bedrooms; instead you need to exit with your luggage wait for the elevator take it up one floorVery spacious Kitchen is fully equipped
6. Remodelled residence perfect for six guests
This apartment was completely remodelled and renovated in 2016 and became a great option mostly for travelling professionals. It is located on the 50th floor and with almost 1300 square feet (!20.8 square meters) available for you. Just two blocks away from the Magnificent Mile and downtown Chicago, the building offers outstanding amenities such as a private theatre, gym, a party room and even an on-site dry cleaning. The outdoor pool and the barbecue deck will help you relax after a long day of meetings. This apartment is an ideal choice for professionals visiting the city with their family for a couple of months.
Top guest reviews
Host:
Good views and decoration responsive hostJill is easy to work with and responds quickly to all questionsBuilding has a nice grill deck with BBQs tables and chase lounges movie theatre dry cleaner and a huge party roomall new and amazing 50th floor viewThe building is secure with 24/7 doorman who is friendly and helpfulLocation:
The building is a safe and amazing location with a short walk to Rush Street and moreThe location is the BEST in the city of Chicago 3 blocks from trump tower and 2 blocks off Michigan Ave Location asideIn morning we walked 2 blocks to Mag mile for shoppingit offers day and night city views that are just breathtakingThis property is also located blocks from the best restaurants nightclubs and rooftop loungesCleanliness:
It can only be described as spacious elegant yet comfortable and beautifully decoratedRead more reviewsAmenities & Room:
then the top of the Hancock tower and the condo is furnished like the Four SeasonsIncredible views and enough space for 6-8 people to have privacy and full kitchen access cable tv and a list of local deliveries availableThe best spot in the unit for us was the bench seating in the living room areaI don't usually take the time to write reviews as I'm always on the roadThe decor and furniture gives you a feel of being in a high-end furniture showroom
7. World-class apartment next to the Magnificent Mile
A few steps away from the Magnificent Mile, this luxurious building has everything you can imagine. From a seafood restaurant in the 1st floor to relaxing amenities such as the pool, the gym and the hot tub, to a magnificent patio with barbecue options and finally a skylounge suitable for drinks and with pool tables. The apartment itself is a two-bedroom house, with queen size beds and high-end appliances in the kitchen. All this will make it difficult for you to leave the apartment and visit the nearby restaurants. Maybe, only go for some shopping?
Top guest reviews
Host:
In fact we are trying to find out what make the mattress is Top recommendationsFurnishings were good not greatThe actual check in policy is a little weird to say the least I am familiar concierge check ins butI received daily emails and several text to confirm my check inThe apartment was clean spare but met our needs and Max was extremely responsive to our every needLocation:
A good choice with an excellent location right by a metro stationJust made it a little difficult to get readyand not a big dealA little unusual way of getting the key and into the placebut once we did itCleanliness:
I was never contacted again and no pillows were dropped off Total poor formThe condo and building are very nice and had everything we neededRead more reviewsAmenities & Room:
Couch and master bed were adequate but have stayed in more comfortable accomodations for the priceThe condo is perfect and as great as it looked in the picturesit would be nice to have a dresser or chest of drawers in each room" I decided to just use the couch pillow one more night and appreciated the effortI eventually got a call and text that second night I was told " I will drop off new pillows in the morning
8. Upscale home in River North
Right in the heart of River North and with an exquisite view of the lake and the city, you will find this two bedroom apartment. Due to the fact that it is located on a very high floor and the floor-to-ceiling windows, it offers breathtaking views. The location is ideal for a short vacation to explore the city of Chicago since right beside the location there are bus and metro stops and the building offers you great amenities to get some rest. You can relax in the pool, the hot tub or the sauna and in the end, in the high-quality beds. You can prepare a full meal in the luxurious kitchen and then enjoy the view from the balcony.
Top guest reviews
Host:
Great location and very nice accommodationswas somewhat more tired and grimyWe stayed here with our two teenage daughters and loved the location as well as the beautiful outdoor pool for relaxing between sightseeingEvery thing was great except I had difficulty contacting the property owner and having the address suppliedand so we did not find out what they would do if they did find out The photographs of the apartmentLocation:
The apartment block is nicely located on the north side of the city centre within walking distance of some great restaurants and the "360" towerdid not represent the actual apartment that we stayed in OursWe were also provided with a cover story in the event that we were challenged Fortunately the building owners remained blissfully ignorant of thisWe were somewhat perturbed by the need to sneak into the property through the car park so that the management of the apartment block remain unaware that the landlord is sub-letting the property (th...Cleanliness:
Very clean and has a great viewRead more reviewsAmenities & Room:
This is a comfortable and spacious apartment with every amenity
9. Artistic apartment with an elegant touch
Just a short ride away from the centre of the Magnificent Mile, you will find this luxurious building. In this high-end apartment, you will find artistic decoration from local artists, high-quality mattresses and a gourmet kitchen stocked with freshly roasted coffee beans. The building offers you a 24/7 suite support, a sundeck with a great view, and a gym. This is a great option when you visit Chicago for work.
Top guest reviews
Host:
the code they gave me did not workgo through all the reservation info only for the guy to tell me the codeThis property was all that was advertised and moreLittle issues that could have been avoided Would book again just not with a heat only optionLyric responded quickly to all questions and seemed very genuinely interested in our experience being top-notchLocation:
Conveniently located grocery store adjacent to buildingWe Stayed Thursday to Sunday and enjoyed every moment of itit was just way too warmThat's on the plus sideAt this time of year end of April the building either has heat or A/C Really could not turn off the heatCleanliness:
The condo was spacious and tastefully decoratedRead more reviewsAmenities & Room:
Amazing condo with incredible viewsAlso needed light bulbs in bedrooms still would stay here againbut they DO have control of the description of the unit and no place in the listing of amenities size of roomsThe apartment was spotless and provided all that we needed and moreIt was everything we expected
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
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