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Top 10 Vrbo Vacation Rentals In Chicago, Illinois - Updated 2020

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Chicago, Illinois sits on Lake Michigan. It’s the most populated city in the Midwest and the third-most populous in the USA. It has an iconic skyline, featuring skyscrapers like the John Hancock Center and the Willis Tower (formerly the Sears Tower). There’s plenty to do in the Windy City, from a visit to Navy Pier to shopping on the Magnificent Mile to visiting one of the many museums. The city is known for its visual arts, improvisational comedy, music, and sports teams. Each neighborhood has its own feel, so it’s well worth exploring the restaurants and night life, as well as the major tourist spots.

Whatever your interests, you’re bound to find something you’ll enjoy in Chicago! And, of course, you’ll need a place to stay. Chicago is chock full of luxury rentals, so there will be plenty of opportunities to relax after a busy day exploring the city. Read on to see our top 10 Vrbo vacation rentals.

1. Skyline high-rise apartment (from 500 USD)

This condo has all the amenities of home, with the luxury of upscale living. There is a fully functioning kitchen, a washing machine and dryer, and cable television. You’ll also be able to enjoy the building’s fitness room, the communal pool and hot tub, and a private balcony with an outdoor grill.

It’s a great spot for a romantic getaway. The master bedroom features a king size bed, with a master bathroom which has both a tub to soak in and a large shower. The condo is in a high-rise apartment, making it a great spot to take in views after a day exploring the Windy City.

The condo is perfectly located, too. It is right next to Grant Park, so you’ll be walking distance to places like the Art Institute of Chicago, Navy Pier, and the Shedd Aquarium. The L train also stops nearby, so it will be easy to explore other areas of the city as well.

Skyline high-rise apartment

Price: from 500 USD

Number of Guests: 4

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2. Large family-friendly apartment (from 699 USD)

If you’ll be traveling with family or friends, this apartment located in the historic and affluent Gold Coast neighborhood is a great option. It can comfortably sleep eight and has all the amenities you’d need and then some! For families with small children, the hosts provide strollers, car seats, and a Pack and Play.

The apartment has a large outdoor deck and is steps away from the beach on Lake Michigan, so if you like to spend time outdoors, this is an ideal spot for you. The deck has an outdoor grill, and the hosts provide beach towels, so you don’t need to worry about bringing anything! You’ll find three bedrooms in the home, one which has a king size bed and two with queen size beds. There is also a queen size pull out couch in the living room.

There are 2.5 baths, which have been renovated with marble and onyx. One bathroom has a jetted tub, providing a great spot to relax. On top of all that, the location is great too! You’ll be just a stone’s throw from Magnificent Mile and very near to transport links to other areas of the city.

Large family-friendly apartment

Price: from 699 USD

Number of Guests: 8

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3. Luxury two-bedroom apartment (from 395 USD)

If you enjoy luxury when you travel, this apartment is for you! Located on the 39th floor of a highrise building, you’ll find plenty to keep you relaxed or entertained. The apartment itself is well-decorated and modern, featuring granite countertops, a washer and dryer, a large private balcony, and three High-Definition TVs.

The complex itself has a 24-hour door attendant, an outdoor pool and sauna, a fitness center, a library, and an on-site supermarket. And that’s just naming a few of the amenities! You’ll also be within walking distance to Chicago’s famous shopping areas, restaurants, and transportation links. This is an exceptional place to stay, with no shortage of things to do!

Luxury two-bedroom apartment

Price: from 395 USD

Number of Guests: 6

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4. Al Capone unit (from 349 USD)

History lovers will enjoy this apartment! This unit is one of seven in a vintage building, with each unit highlighting a celebrity or historical figure. Al Capone, which this unit highlights, rose to fame as an American gangster, leading the Chicago Mob in the 1920s.

This apartment is great for a couple who like brand new decor, but who don’t necessarily need luxury amenities in the apartment itself. The unit contains a bedroom with a queen sized bed and a private bathroom. The common area allows access to a barbecue, fire pit, and a kitchen area with a stocked fridge and snacks. It’s in a great location, with many attractions walkable. The Museum of Contemporary Art, the Magnificent Mile, and Navy Pier are all nearby.

Al Capone unit

Price: from 349 USD

Number of Guests: 2

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5. Quiet and comfy two-bedroom apartment (from USD 107)

For those who are hip and artistic, check out this two-bedroom apartment in the Lincoln Square neighborhood in north Chicago. Lincoln Square is known for its German roots and has recently become a trendy spot with plenty of bars, restaurants, and unique shops. This apartment fits right into the neighborhood! The apartment is decorated in a colorful way, with each room feeling different than the last.

There are two bedrooms, so this is a good spot for a variety of travelers: couples, a family, or a group of friends. While there’s plenty to explore in Lincoln Square, if you prefer to cook at home, there’s a fully functional kitchen and a backyard with a grill. There’s a grocery store right across the street, so picking up supplies for a homemade dinner is incredibly easy!

When you’re done exploring all that the neighborhood has to offer, an L train stop is a short walk away. Downtown Chicago is just a 20-minute train ride from the apartment. This colorful apartment provides the perfect place to explore hip, local culture as well as all the sites Chicago has to offer.

Quiet And Comfy 2-BR In Lincoln Square Easily Sleeps 4 to 5 - Great Intro Rates
104 reviews
Apartment 5 Guests 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
we would recommend it to anyone needing a 2 bedroom apt
it was very clean and accommodating everything we needed
clean inviting space in a lovely neighborhood with lots to do
virgil’s place is nice and clean and virgil is a wonderful host
the manager virgil was extremely responsive
the property owner was easy to deal with and very flexible
virgil was a great host and very flexible about check out time
comfortable accommodations and owner very nice and easy to communicate with
the owner virgil was very responsive to any inquires
my wife and i loved the location due to the close proximity to great restaurants park and train
we really enjoyed our stay it was near places to eat and grocery shop
the neighborhood is nice for beautiful walks and good places to eat
nice place in a good leafy and safe neighborhood just a bit far from the center
the newly remodeled aldi is right across the street and is super convenient
Read more reviews

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6. Luxury studio suite (from 272 USD)

This studio suite is great for a couple who want to be near all the action and who enjoy the amenities of luxury apartments. The apartment itself fits two people. It has an updated kitchen, cable TV, and a balcony to enjoy the beautiful views from this high-rise building. You’ll also be able to enjoy the communal pool and fitness center.

Reviewers gush about the location of this studio suite. Located in the Streeterville neighborhood, you’ll be a 20-minute walk away from shopping on the Magnificent Mile, Navy Pier, and museums. There are plenty of bars and restaurants in the area, and the front desk staff is on hand to give recommendations and directions.

Luxury studio suite

Price: from 272 USD

Number of Guests: 2

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7. Luxurious vintage condo (from USD 120)

This quiet condo in an Art Deco building has all you need for a comfortable stay. The condo has an open plan kitchen and dining room, with all the amenities you’d need, granite counter tops, and custom cabinets. It has two large bathrooms, one with a jet tub and shower and the other with a large walk-in shower. Both bathrooms have heated floors, keeping you warm on a cold winter night!

There are two bedrooms with large beds and a double sofa bed, meaning six people can sleep here. The condo also has a fireplace in the kitchen and a private garden––two great spaces to relax in! The condo is on the Evanston border, in the northern part of Chicago.

This makes it a great place to stay for fans of Northwestern University and Loyola University sports teams. It’s also a short distance from downtown Chicago. In 20 minutes, you can explore all the city has to offer. Reviewers love how clean and comfortable the condo is and enjoy the short walk to the nearest L station.

Vintage Condo with Whirlpool Tub, Fireplace and Open Floor Plan. Mins. to Lak
97 reviews
condo 6 Guests 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
this is a beautiful condo with modern amenities such as a fully equipped kitchen with elegant design
the property is very nice the beds were comfortable (the sofa bed wasn't bad
the bathrooms have heated floors the whirlpool was a nice feature as well
the kitchen was well stocked as well as all the linens
the place was very clean
it was nicely decorated very clean and comfortable
the owner is helpful and accomodating
ross was very helpful when we checked in
i love the hosts
ross was extremely very helpful and nice
ross meet us when we arrived and was very helpful
lovely condo in a really quiet neighborhood
close to grocery restaurants and anything you need fir a great weekend
i just got engaged in this condo this place is fabulous its close to everything by car and quiet
the condo is nicely furnished and allows us a place to relax and to cook if we choose
the apt was well stocked with kitchen supplies (dishes pots and pans etc)location worked great for us
Read more reviews

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8. Vintage and modernized four-bedroom condo (from 664 USD)

This modern condo is the perfect spot for large groups or families! It’s spread out over two floors and is newly renovated. The property boasts two kitchens and a wet bar. There are also two fireplaces, a washing machine and dryer, four flat screen TVs, and an outdoor sitting area with a grill. There are four big bedrooms and a sofa bed, so 12 people can sleep here.

There are also four bathrooms, so plenty of space for the whole family to get ready in the morning! On top of a large amount of space on offer, the condo is located in River North, meaning much of Chicago is within walking distance. If you’ve got a large group and also want some private space, this is a great spot!

Vintage and modernized four-bedroom condo

Price: from 664 USD

Number of Guests: 12

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9. Studio loft (from 247 USD)

This studio loft checks all the boxes! It’s beautifully furnished, the building has great amenities, and it’s in a great neighborhood. Up to four people can stay here. The apartment has one king sized bed, one single bed, and a single sofa bed.

The kitchen is fully functional, so you’ll be able to cook at home if you choose. The building also boasts a communal deck, hot tub, game room, bike room, and a fitness center. You’re also a short walk from many of Chicago’s sights and a short train ride from downtown.

Studio loft

Price: from 247 USD

Number of Guests: 4

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10. Vintage four-bedroom apartment (from USD 200)

Last but not least on our list is another apartment in the quirky, up-and-coming neighborhood of Lincoln Square. This large apartment can sleep eight people in four bedrooms. There are two bathrooms, a fully-functional kitchen, and an outdoor deck with a grill. Reviewers are happy with how homey the apartment feels. With enough space to spread out and plenty of rooms, you can enjoy one another’s company or head to a different room for a bit of peace and quiet.

You’re perfectly set up to explore the unique shops and restaurants in the neighborhood. There’s plenty to chose from, many of which are practically right outside the front door. Getting to downtown Chicago is easy as well. Just hop on the L and you’ll be downtown in 20 minutes. This is the perfect spot for your family to explore the hot tourist spots, as well as local sights unique to the neighborhood.

Great Family Retreat in Lincoln Square *Free WiFi *Back Patio *Grill *Cable TV
119 reviews
Apartment 10 Guests 4 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
furnishings are old fashioned but comfortable
beds were so comfortable and we loved the back patio
house was very clean and maintained
home was clean a great area thanks for having us
we loved our stay owner was awesome
great location great space for large family
location was great and convenient to other chicago neighborhoods as we well
my wife was running and it was a perfect location
plenty of fun to be had within a short drive or even walking distance
easy parking easy to the train or bus a cool old house in a quiet neighborhood
Read more reviews

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Plenty of luxury in Chicago

Whether you’re a couple on a romantic getaway or a family or group of friends, there’s no shortage of luxury amenities to be found in the vacation rentals in the Windy City. You can come back from a day exploring the city and relax on the deck, swim in a communal pool, or work out in a fitness center. You just have to book the vacation rental that suits you the most and be prepared to be wowed by all Chicago has to offer!

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Nicole is an American expat living in London, England. When she moved from the midwest to London in 2012, it was her first time leaving the US. She has traveled steadily since then, making trips...Read more

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