Top 13 Vrbo Vacation Rentals In Chicago, Illinois - Updated 2024

vrbo chicago
| 7 min read

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 famous buildings like the John Hancock Center and the Willis Tower (formerly the Sears Tower). There are things to do, especially with kids, 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 nightlife, 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. Check out this list of the best Vrbo vacation rentals in Chicago, 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 April 04, 2024.

1. Luxurious house perfect for large groups (from USD 1150)

Boasting a space of 4,200 square feet (390.19 square meters), this upscale house has 11 beds inside. Because of this, up to 21 people can be accommodated here, making this rental the best choice for large groups.

In addition to the many beds, you can find other luxurious amenities. The kitchen has premium appliances and utensils, so you can easily prepare a feast for everyone, and there are three 50-in televisions, all with cable access. There’s also a game room with a pool table and a variety of board games and playing cards.

To make the most of your vacation, you should check out the various attractions nearby. The shores of Lake Michigan are just a few blocks away, so you only have to take a short walk to reach this destination. Other must-see attractions include North Avenue Beach and Navy Pier.

Stayed at this property?
Chicago, Illinois, United States
3.48 km (2.2 mi) from Horner (Henry) Park
PRIVATE VACATION HOME 21 Guests 6 Bedrooms 4 Bathrooms

Top guest reviews
Amenities & Room:
nice dining area w/ large table to fit a large family
it looks just like the pictures with comfortable beds eclectic decor comfortable beds and lots of space
the yard is perfect for a bbq with room for games
there's plenty of space for all to relax and gather in a lovely comfortable setting
the kitchen utensils were perfect to prepare a wonderful large family meal
the place was clean w/ nice features
the house itself was very clean and organized
the house was very clean and well equipped
the house was clean throughout and overall quite charming
the rooms were clean and looked exactly as the pictures posted
the owners were excellent and treated us very well
the owners were helpful with all questions we had and responded quickly
they were very accommodating and helpful
the owner was very responsive to our needs
ana was a very gracious host and quick to respond to any questions we had
the location was golden for having fun downtown
the location offered a variety of restaurants and a great walk to montrose beach
the neighborhood is great to walk around
it’s a beautiful house that’s walking distance to anything you’ll need
loved that target/aldi were a quick walk incase someone forgot something
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2. Lovely studio room with a secluded garden in Logan Square (from USD 123)

This studio unit comes with 350 square feet (32.52 square meters) of space, which means that this is perfect for solo travelers or couples. Inside, there’s a plush queen-size bed, as well as a well-equipped kitchenette and a cozy living area with wireless internet and cable television. Outside, you can find a secluded garden, where you can lounge and relax after a long day.

This rental is located in the vibrant neighborhood of Logan Square, so many iconic Chicago attractions are nearby. Some of the places that you might want to visit during your stay include Lincoln Park Zoo, Water Tower Place, Chicago River Walk, and State Street.

Stayed at this property?

4.26 km (2.7 mi) from Horner (Henry) Park
54 reviews   Wifi Available
House 2 Guests 0 Bedrooms 1 Bathroom

Accommodates: 2
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
the room was good
the room is attractive and cozy
the room was in the whole very clean
monica is a delightful host
gracious and helpful host who was available but not in our way
monica is the quintessential host her eye for design is unparalleled our stay was perfect
we had the pleasure of getting to meet our host monica
great neighborhood very quiet overall and felt friendly and safe late into the night
convenient to the bus and not far from the 606 trail for a fun bike ride
good neighborhood with a market right around the corner and close restaurants
great location and very nice outside area
thanks for making it so easy to stay and love the location
great hosts in a great location in logan square
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3. Converted storefront with a bright and airy space (from USD 234)

This Vrbo rental used to be a storefront, and even though it’s now been converted, it still features the typical large glass facade. The interior is always awash with bright light, and you’ll be able to glimpse the streets from the living room and kitchen area.

The bedroom is on the loft upstairs, and it’s equipped with a queen-size bed and a television, allowing you to watch movies or shows while laying down. There’s also a dedicated workspace if you ever need it.

If you’re bringing a child with you, they’ll find many things to do here as well. There are games available, and if you want to go out, you can visit the museums and zoos nearby, such as Lincoln Park Zoo and the Chicago Museum of Science and Industry.

Stayed at this property?
Chicago, Illinois, United States
5.45 km (3.4 mi) from Horner (Henry) Park
Apartment 4 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Amenities & Room:
this is a lovely unique loft with loads of character and style with strong wifi
they thought of little details like stocking the bathroom with toiletries
bed not up to ritz standards but all clean and works
the hosts were very flexible and responsive
amy was highly responsive when we were booking the property and made the check in and parking process easy
amazing location close to everything lincoln park and short walk to l
the apartment has a great location in an excellent neighborhood close to the train and shopping
great location close to everything and very quiet
great location close to shopping and restaurants on armitage halsted and north ave
the unit is located in a great area of the city and we were able to walk everywhere
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4. Comfy bungalow near a dog park (from USD 119)

This two-bedroom bungalow has a maximum capacity of four people. It also welcomes up to two dogs for a fee and provides dog bowls and a dog bed. The living room features a 55-inch TV with gaming capabilities and a vinyl turntable, as well as board games and books, for your entertainment. The kitchen has a fridge, microwave, and waffle maker for your cooking needs.

There’s a nearby dog park where you can take your furry friend. Wrigley Field and Lincoln Park Zoo are less than 9 mi (14 km) from the rental.

Stayed at this property?

6.59 km (4.1 mi) from Horner (Henry) Park
50 reviews   Wifi Available
House 10 Guests 2 Bedrooms 1 Bathroom

Accommodates: 10
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
her upstairs apartment is well furnished as well as well appointed
the rooms were clean and organized
absolutey adorable place very clean and comfortable
very clean and outfitted with absolutely everything one needs
it was a nice area the house was very clean and had great amenities
good layout clean very comfortable well maintained appropriately attentive host what's not to like
jamie was the perfect host
hostess was very helpful and we had a great stay
jamie is very personable attentive and concerned that the experience is a positive one
and jamie is super sweet and very accommodating
the location is close to expressways so getting to downtown or o'hare is an easy trip
nice simple house in a great location
there are several good restaurants within walking distance
the neighborhood was safe & quiet
great north side location convenient to a variety of food options and services
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5. 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

Stayed at this property?

6. 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

Stayed at this property?

7. 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

Stayed at this property?

8. 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

Stayed at this property?

9. 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

Stayed at this property?

10. Luxurious vintage condo

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.

Stayed at this property?

6.45 km (4.1 mi) from Horner (Henry) Park
108 reviews   Wifi Available
condo 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

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
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11. 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

Stayed at this property?

12. 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

Stayed at this property?

13. Clean and spacious studio inside a high-rise building

With a queen-size bed and a sofa bed, this studio can accommodate a maximum of three people. Inside this unit, you can also find a dedicated workspace, a well-equipped kitchen, and a smart television for entertainment. There’s also a heater, so you don’t need to worry about the Chicago winter.

Some of the must-see landmarks nearby include Millennium Park, Water Tower Place, Chicago Water Tower, Navy Pier, and the Art Institute of Chicago. There are also many shops and restaurants close by, so if you ever need to eat or shop for souvenirs, you only have to go out and explore the area.

Stayed at this property?

9.28 km (5.8 mi) from Horner (Henry) Park
28 reviews   Wifi Available
studio 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
room looked like it did in the pictures
we had a great stay at dee's apartment
overall the room was clean and it was a very pleasant stay
it was spacious clean and stocked with everything you may need
great location - very walking friendly very clean seamless check-in/check-out secure access good communication responsive communication
clean easy to get to i worked on site remote and wifi was strong
host was a good communicator and addressed issues/questions that i raised
beautiful apartment and friendly host we will stay here again
the hostess was very accommodating and responsive
the host was very communicative location was fantastic
highly recommend cafecito across the street for breakfast lunch or dinner at a really tourist-friendly price
great location for walking and enjoying the city
walking just a few blocks gave you access to the best shopping in the chicago area
the neighborhood is quiet safe and easily accessible to all the excitement downtown
perfect downtown location for what we wanted to do which was eat shop and sightsee
great location right off the lake shore
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 Vrbo accommodation in Chicago, Illinois, that suits you the most, and be prepared to be wowed by everything this city has to offer!

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
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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