Chicago of the Big Shoulders, also known as the Windy City, is one of the United States’ largest cities. For years, it has served as the playground for adventurous architects, aspiring comedians, and that famous deep-dish pizza, among many other things. Its city skyline is also one of the most recognized, with towering skyscrapers serving as distinctive peaks. Whether you’re looking for arts and culture, great shopping, and a gastronomic scene worth exploring, Chicago offers it all. For a slice of Chicago life, we highly recommend staying at one of the many Vrbos scattered in and around Chicago. Your options range from charming brownstones to luxurious penthouses with commanding views of the city. Here are 10 of our absolute favorites. Read on to learn about the best Vrbo accommodations in Chicago North Side, Illinois.
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 March 13, 2023.
1. Hotel-style luxury accommodation with breathtaking views (from USD 190)
The sky is the limit at this two-bedroom, two-bathroom condo unit located on the skyscraper’s 51st floor. You’ll feel like the king (or queen) of Chicago here, with views extending as far as Lake Michigan. Best of all, you get to stay in the thick of things, right at the border of Gold Coast and River North. Without a doubt, this is one of the most exciting Vrbos in Chicago.
Each bedroom here has its own walk-in closet with plenty of storage. The gourmet kitchen is both gorgeous and functional, equipped with stainless steel appliances. This Vrbo certainly goes above and beyond!
1.44 km (0.9 mi) from Millennium ParkAccommodates: 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 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 inHost:
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 cityRead more reviewsLocation:
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 corner
2. Modern and sleek condo high above the city (from USD 361)
If you want a high-rise unit but don’t want to deal with too much space, this one’s for you. Sitting pretty on the 50th floor of this modern penthouse unit is a great fit for couples and small groups. It has two bedrooms, two bathrooms, all equipped with everything you and your companions need. From here, River North is due west, while North Michigan Avenue and all its glamour are also a short distance away. Floor-to-ceiling windows will give you dramatic views of the Windy City’s skyline and Lake Michigan.
1.16 km (0.8 mi) from Millennium ParkAccommodates: 4
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Amenities & Room:
The condo is remarkable: Striking viewsa well equipped kitchen bathroom and very comfortable bedsThe hideaway bed in the living space was great for kidsthe owners were outstanding in communicating all the key info needed for access and parkingAppreciated being able to do laundryCleanliness:
The apartment was impeccably clean and decorated tastefullyThe apartment was exactly as picturedI do have to say it was very cleanThe condo itself was very cleanEverything in 5008 was exactly as pictured Plenty of detailed information provided by the owners before our stay in emails and in the apartment on how to work thingsHost:
The doorman was super friendly and helpful alsosuper communication with the ownerFalling in love with Chicagomag mile and the convention centerthey were very helpful with all the informationRead more reviewsLocation:
We loved it's location to restaurantsperfect location close to everythingThe location is River North is perfect for a Chicago vacationThis is a great apartment in clean safe downtown neighborhoodThe view from the patio is spectacular
3. Luxury penthouse overlooking Magnificent Mile (from USD 347)
Looking to experience luxury high-rise living in Chicago? This penthouse might just be the answer. Situated on the 51st floor of a towering skyscraper in River North, this one-bedroom, one-bathroom suite has some of the most dramatic views of the city. Come nighttime, you can admire the glittering skyline all while enjoying the warmth of the fireplace. This Magnificent Mile penthouse is best suited for couples, so bring a loved one and treat him or her to a staycation at this spectacular high-rise retreat.
1.16 km (0.8 mi) from Millennium ParkAccommodates: 4
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Amenities & Room:
The view was breathtaking from our condoThe views in the condo are incredibleThe views are terrific and the condo was wonderfulThe queen bed was great shower and bathroomParking access was easy Would stay againCleanliness:
They unit was exactly as described andsuper clean and nice Process was seamless to check-in and outHost:
Our condo hosts were very gracious and timely in helping guide us with garage/driving directionsWe have rented apartments through VRBO in the US and EuropeThey do have several movie channels though via satellite(Owner claims no furniture allowed )Despite the cooler weather we experienced while on vacation the condo was so close to all the places we wanted to check out that we just ended up walkingRead more reviewsLocation:
The location is central and located next to the red lineThe location in Chicago was very convenientThere is a full grocery store on the main floor of the building which was great for breakfast and snacksand we took Uber to the Museum of Science and IndustryThe views from this condo are amazing
Prepare to explore Chicago
Now that you’ve chosen the Vrbo that fits your needs and itinerary, it’s time to experience everything that Chicago has to offer. Browse our website for Chicago travel guides to find the best eats, shopping, and art in the city.
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