The 12 Best Downtown Chicago Vrbo Vacation Rentals

Chicago is a world-class city with world-class attractions. There is, after all, a reason why so many people have made the city their home. Chicago isn’t just any big city. It is a unique metropolis shaped by its people, history, and geography. No visit is complete without a stroll along Lake Michigan and walk through the adjacent parks or perhaps a visit to the historical Wrigley Field. From the culinary arts to the visual and theatrical, Chicago boasts a wide range of attractions for visitors to enjoy.

One factor that makes getting the most out of a Chicago getaway especially practical is the density of the downtown area. The Loop covers just 1.5 square miles of land, but many of the city’s most popular points of interest are within The Loop or a short distance away. Now there is plenty to see outside of The Loop, but for first-time visitors keen to see the very best the city has to offer, there is plenty to see, do, and photograph without straying far from downtown. It is safe, full of things to do, well-served by public transportation, and really quite walkable. For these reasons, staying downtown just makes sense.

Even with narrowing your search to downtown Chicago, there is still a large selection of vacation rentals available. So, we did the work for you! Here is a list of 12 of the best Vrbo condos/apartments and house rentals to stay downtown. Each of the properties below gives visitors easy access to the city’s best experiences.

Apartment In 55th-Floor Penthouse

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$946.00/avg nightly

What a life it must be to always have a living room like the window-filled marvel in this towering building! Set in a great location, the high ceilings and plentiful windows give visitors incredible views of downtown and Lake Michigan. There’s even a wrap-around balcony for those not content to enjoy the city from inside.

With two queen bedrooms and a king, every guest gets a luxurious treatment. If you’re bringing extra guests, don’t worry: The futon in the living room might actually be the nicest place to sleep given the fireplace and fantastic view. The apartment rental’s building has a gym, swimming pool, and even a grocery store on the ground level.

Bedrooms: 3

Bathrooms: 2

Sleeps: 8

Luxury Skyhouse In The West Loop

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$675.00/avg nightly

Wake up, scratch your eyes, and gawk at the size of the big city while looking out from floor-to-ceiling windows in this fabulous apartment. All three queen bedrooms are blessed with amazing views, as is the elegant big city kitchen.

Guests have access to all the building’s amenities, including a swimming pool, fitness studio, and rooftop terrace. As an added perk, there is no extra charge to make use of the below-ground parking garage. But, given the proximity of trains and more, driving is definitely optional.

Bedrooms: 3

Bathrooms: 3

Sleeps: 6

Luxe Loft Off Grant Park

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$350.00/avg nightly

An elegant example of contemporary minimalist design, this loft apartment brings you right where the action is. There isn’t space here to mention all the excellent restaurants and attractions a short walk away, but know that they’re out there.

Just two blocks from Grant Park, it’s a particularly great stay if you’re coming for one of the many events hosted there. In addition to the two bedrooms, there’s room for plenty of fellow visitors on the two beautifully designed sofas and air mattresses. 

Bedrooms: 2

Bathrooms: 1

Sleeps: 6

Glass Penthouse On The Lake

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$1,016.00/avg nightly

Looking out from the windows of this fine penthouse, nothing separates you from the placid waters of Lake Michigan — except for 556 vertical feet. Enjoy spectacular views of the water and iconic skyline amidst stylish surroundings. Light floods in through the many windows, illuminating the kitchen, common area, and each of the three bedrooms. 

Guests also get access to the building amenities, including an outdoor courtyard, lounge, gym, and pool. With the lake so close, guests will find themselves drawn to the famous Navy Pier. You’ll also probably find your head flooded with ideas about taking a boat trip out on the lake.

Bedrooms: 3

Bathrooms: 3

Sleeps: 8

Penthouse On The 13th Floor

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$613.00/avg nightly

Spacious and enviably located, this downtown penthouse is a great way to see Chicago. There’s so much to see in the city, and, if you stay here, you needn’t even leave the house to take a lot of it in. With high ceilings, oversized windows, and a balcony, this apartment boasts commanding views.

If that weren’t enough, visitors can also take in the panorama from the rooftop deck. One block down from the park and three from the river, the location is certainly something. This 1,400-square-foot property has two queen bedrooms, one full, and room for two more on the futon.

Bedrooms: 3

Bathrooms: 2

Sleeps: 8

Light-Filled Penthouse Condo

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$335.00/avg nightly

The flowers, plants, and floral designs make this 8th-floor penthouse feel uncannily quaint for a tall structure in America’s third-largest city. With nothing above but the sky, the architects have given this apartment high ceilings and plenty of windows.

Enjoy peace of mind in one of the city’s safest neighborhoods. Walk without worry to Shedd Aquarium, Millennium Park, the Adler Planetarium, and many more attractions. Great for a family looking for a comfortable temporary home in Chicago.

Bedrooms: 2

Bathrooms: 1

Sleeps: 7

Sonder Jewelers Row

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$236.00/avg nightly

Elegant and modern, this one-bedroom apartment on Jewelers Row is perfect for a couple heading to the Windy City. Whether you intend to buy a ring or not, the shops downstairs are absolutely worth a visit.

Designed with a minimalistic and modern style, the apartment is a comfortable space for two. Countless sites are within walking distance, from the famous Bean to the theater district. This is an affordable option for a couple or individual ready to get out and see America’s third-largest city.

Bedrooms: 1

Bathrooms: 1

Sleeps: 2

Luxurious Apartment With A View Of Navy Pier

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$861.00/avg nightly

Discover Chicago in comfort from this Streeterville apartment. Enjoy views of Navy Pier and its grand Ferris wheel from home before venturing out to explore the city’s cherished lakefront treasure.

The apartment comfortably sleeps six across three bedrooms and there’s room for additional guests on the fold-out mattress should your party require it. The building also has a state-of-the-art gym, pool, and private cabanas. 

Bedrooms: 3

Bathrooms: 3

Sleeps: 8

Contemporary South Loop Studio

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$278.00/avg nightly

There’s so much for couples to do in Chicago, whatever their interests and passions. This downtown studio by Kasa is one fine way to find out what memorable moments a visit to Chicago can bring into your life.

Each Kasa apartment has a unique design and it shows. These are no bland hotel rooms; they’re curated contemporary spaces to live, not mere sleeping spots. With a luxurious king bed and full kitchen, you’ll find everything you need and some pleasant delights you’d never expect. What’s more, this apartment is pet friendly.

Bedrooms: 1

Bathrooms: 1

Sleeps: 2

River North’s Rock ’N’ Roll

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$362.00/avg nightly

Just six blocks away from Michigan Avenue, this rock-and-roll-themed apartment offers guests a taste of life in the big city. The classic exposed brick walls are decorated with images of famous rock musicians. Guitars also form an integral part of the decor.

The two queen bedrooms are true gems. One has a rare four-poster bed with white mesh and the other has a nice quilted duvet. Be advised that the apartment is a second-floor walk-up.

Bedrooms: 2

Bathrooms: 2

Sleeps: 6

Private Home In The Near North Side

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$559.00/avg nightly

Most Chicagoans live in high-rise apartments. That doesn’t mean it isn’t possible to spend your visit in a genuine house. This huge home is just that: a house with a backyard and other homey fixtures.

Located in a quiet neighborhood just north of what is considered downtown, this is a great place for a large group to see a different side of Chicago. The Loop is still close, but the location almost feels suburban. The house has two kitchens and two entrances, easily accommodating a very large group while preserving privacy.

Bedrooms: 5

Bathrooms: 4

Sleeps: 24

The Guild

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$451.00/avg nightly

This two-bedroom condo in Streeterville is ideal for a small group headed out to take in Chicago’s many sights. Fully furnished from kitchen to bathroom and located mere blocks away from Navy Pier and the contemporary art museum, visitors staying here needn’t worry much about getting around.

You’ll be just seconds away from the lake as well as the culinary delights of The Magnificent Mile. The homey decor will make you feel, well, right at home. Additional guests can be hosted on three fold-out sofas.

Bedrooms: 2

Bathrooms: 2

Sleeps: 7

To discover the best things to do (and eat!) while visiting Chicago, check out:

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