The 12 Best Downtown Chicago Vacation Rentals Vrbo

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

The density of downtown is a factor in making the most of a Chicago getaway. 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’s plenty to see outside of The Loop, but for first-time visitors eager to see the best of the city, there’s plenty to see, do, and photograph without straying far from downtown. It’s safe, plenty to do, well served by public transport and really very walkable. For these reasons, staying downtown makes sense.

Even limiting your search to downtown Chicago, there is still a great selection of vacation rentals available. Then we have done the work for you! Here’s a list of 12 of the best Vrbo condo/apartment and house rentals to stay downtown. Each of the properties below offers visitors easy access to the best experiences in town.

Apartment in Penthouse on the 55th Floor

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$946.00/avg per night

What a life it must be to always have a living room like the wonder filled with windows in this imposing building! Situated in an ideal location, the high ceilings and many windows provide visitors with incredible views of downtown and Lake Michigan. There’s even a wrap-around balcony for those who aren’t content to enjoy the city from within.

With two queen bedrooms and one king bed, each guest receives luxurious treatment. If you’re bringing extra guests, don’t worry: the futon in the living room might actually be the best place to sleep given the fireplace and the fantastic view. The apartment rental building has a gym, swimming pool, and even a convenience store on the ground floor.

Bedrooms: 3

Bathrooms : 2

Sleeping: 8

Luxury Skyhouse in the West Loop

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$675.00/avg per night

Wake up, scratch your eyes and take in the sheer size of the big city as you gaze out of the floor-to-ceiling windows of this fabulous apartment. All three double bedrooms come with stunning views, as does the stylish big city kitchen.

Guests have access to all building amenities, including a swimming pool, fitness studio, and rooftop terrace. As an added benefit, there is no additional charge for using the underground car park. But, given the proximity to trains and more, driving is definitely optional.

Bedrooms: 3

Bathrooms : 3

Sleeping: 6

Luxury Loft Off Grant Park

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$350.00/avg per night

An elegant example of contemporary minimalist design, this loft apartment takes you where the action is. There’s no space here to mention all the great restaurants and attractions within walking distance, but know they are there.

Just two blocks from Grant Park, it’s an especially pleasant stay if you’re coming for one of the many events held there. In addition to the two bedrooms, there is room for many other visitors on the two beautifully designed sofas and air mattresses.

Bedrooms: 2

Bathrooms : 1

Sleeping: 6

Glass Penthouse On The Lake

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$1,016.00/avg per night

Looking out the windows of this beautiful penthouse, nothing separates you from the calm waters of Lake Michigan – except for 556 vertical feet. Enjoy spectacular views of the water and the iconic skyline in an elegant setting. Light streams in through the many windows, illuminating the kitchen, common area and each of the three bedrooms.

Guests also have access to the building’s amenities, including an outdoor courtyard, lounge, gym, and swimming pool. With the lake so close, guests will be drawn to the famous Navy Pier. You will also likely find your head flooded with ideas for a boat trip on the lake.

Bedrooms: 3

Bathrooms : 3

Sleeping: 8

13th Floor Penthouse

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$613.00/avg per night

Spacious and ideally located, this downtown penthouse is a great way to see Chicago. There is so much to see in the city and if you stay here you don’t even have to leave home to enjoy it. With high ceilings, oversized windows and a balcony, this apartment offers stunning views.

If that wasn’t enough, visitors can also admire the panorama from the rooftop terrace. One block from the park and three from the river, the location is definitely something. This 1,400 square foot property has two double bedrooms, one full, and room for two more on the futon.

Bedrooms: 3

Bathrooms : 2

Sleeping: 8

Bright Penthouse Condo

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$335.00/avg per night

Flowers, plants and floral patterns make this penthouse on the 8th floor Feel eerily quaint for a tall structure in America’s third largest city. With nothing above but the sky, the architects gave this apartment high ceilings and lots of windows.

Enjoy peace of mind in one of the safest neighborhoods in town. Walk carefree to the Shedd Aquarium, Millennium Park, Adler Planetarium and many more attractions. Ideal for a family looking for a comfortable temporary home in Chicago.

Bedrooms: 2

Bathrooms : 1

Sleeping: seven

Survey Jewelers Row

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$236.00/avg per night

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 on the ground floor are absolutely worth a visit.

Designed with a minimalist 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. It’s an affordable option for a couple or someone ready to get out and see the third largest city in the United States.

Bedrooms: 1

Bathrooms : 1

Sleeping: 2

Luxurious apartment overlooking Navy Pier

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$861.00/avg per night

Discover Chicago comfortably from this apartment in Streeterville. Soak up views of Navy Pier and its Ferris wheel from your home before venturing out to discover the city’s prized lakeside treasure.

The apartment can comfortably sleep six people in three bedrooms and there is room for additional guests on the folding mattress should your party require it. The building also features a state-of-the-art gym, swimming pool, and private cabanas.

Bedrooms: 3

Bathrooms : 3

Sleeping: 8

South Loop Contemporary Studio

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$278.00/avg per night

There’s so much for couples to do in Chicago, regardless of their interests and passions. This downtown studio by Kasa is a great way to experience the memorable moments a visit to Chicago can bring to your life.

Each Kasa apartment has a unique design and it shows. These aren’t bland hotel rooms; they are contemporary spaces organized for Direct, not mere sleeping places. With a luxurious king bed and full kitchen, you’ll find everything you need and cozy delights you wouldn’t expect. In addition, this apartment accepts pets.

Bedrooms: 1

Bathrooms : 1

Sleeping: 2

River North Rock’n’Roll

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$362.00/avg per night

Just six blocks from Michigan Avenue, this rock’n’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 are also an integral part of the decor.

The two double bedrooms are real gems. One has a rare four-poster bed in white net and the other has a beautiful quilted duvet. Be aware that the apartment is on the second floor without a lift.

Bedrooms: 2

Bathrooms : 2

Sleeping: 6

Private house in the near north side

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$559.00/avg per night

Most Chicagoans live in high-rise apartments. This does not mean that it is not possible to spend your visit in an authentic house. This huge house is just that: a house with a garden and other welcoming facilities.

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

Bedrooms: 5

Bathrooms : 4

Sleeping: 24

The guild

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$451.00/avg per night

This two bedroom condo in Streeterville is ideal for a small group exploring the many sights of Chicago. Fully furnished from kitchen to bathroom and located just blocks from Navy Pier and the Museum of Contemporary Art, visitors staying here don’t have to worry about getting around.

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

Bedrooms: 2

Bathrooms : 2

Sleeping: seven

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

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