8 Best Vrbo Vacation Rentals Near Chicago Lakefront, Illinois - Updated 2024

Daniel
Daniel 
Updated
| 4 min read

Chicago is well-known as the ‘Windy City’ due to its windy weather. It’s the home of deep-dish pizza. It also has many beautiful lakes. Major attractions in the city include the Fields Museum of Natural History, the Museum of Science and Industry, the Shedd Aquarium, and the Navy Pier, among others. The city is also famous for its history during Prohibition, the time when alcohol consumption and production was banned (except for religious purposes) since it was home to many famous gangsters, illegal speakeasies, and many other places where people who did not approve of Prohibition would find ways to go around it. Also, Chicago was home to the flapper culture of the Roaring Twenties, pre-Depression. However, before you can experience the wonders of Chicago, you have to be able to book the best accommodations. Check out the best Vrbo vacation rentals near Chicago Lakefront, 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 04, 2024.

1. Stone mansion with a hot tub (from USD 250)

Enjoy a delightful stay at this vast historic mansion located near the beach. Chic bars, restaurants, a theater, and a 9-hole golf course are just a short distance away as well. You will also find public tennis courts within walking distance.

There is a hot tub available on the property for your relaxation and enjoyment. When you don’t feel like dining out, use the fully equipped kitchen to whip up something delicious and enjoy dining on the outdoor patio. You can stream movies or shows with the WiFi available here for free.

Stayed at this property?
Chicago, Illinois, United States
17.28 km (10.8 mi) from Museum of Science and Industry, Chicago
Apartment 20 Guests 4 Bedrooms 2 Bathrooms

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2. Lake-view penthouse with gym and club room (from USD 241)

One of the most sought-after places to stay in the city is this stunning accommodation in a lush, upscale area near major attractions. Lakefront Trail and Oak Street Beach are within walking distance of the property. You can enjoy views of the lake from the windows. Moreover, you will also have access to all the amenities of the building, including a gym, rooftop deck, business center, and club room with pool table.

You can prepare your favorite recipes in the fully stocked kitchen and enjoy your meals in the dining space with scenic lake views. Stay connected, updated, and entertained with WiFi.

Stayed at this property?
Chicago, Illinois, United States
12.42 km (7.8 mi) from Museum of Science and Industry, Chicago
Apartment 6 Guests 2 Bedrooms 1 Bathroom

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3. Penthouse apartment with city views (from USD 384)

Experience Chicago from a higher perspective when you stay at this top-floor penthouse apartment in a high-end building. With its high ceilings and oversized windows, this Vrbo in downtown Chicago offers panoramic views of the city skyline. The chic furnishings are paired with fast WiFi and smart TV for complete indoor entertainment. In the fully equipped kitchen, you’ll find the essential tools needed to cook a nice meal. Restful evenings are assured in the three bedrooms with plush beds.

Adjacent to the building’s rooftop terrace with sun beds, lounge seating, and grilling, the penthouse also provides opportunities for outdoor relaxation. You’ll also be given access to other shared facilities including a movie theater, gym, and outdoor pool. Note that parking is not included in this listing and dogs are allowed provided that they’re below 35 pounds (15.9 kilograms).

Stayed at this property?
Chicago, Illinois, United States
11.15 km (7.0 mi) from Museum of Science and Industry, Chicago
Apartment 8 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Cleanliness:
the apartment was very nice and clean
first time i go to chicago the penthouse is beautiful clean i liked it a lot and my family
Host:
host was extremely easy to communicate with and accommodating
the communication with the owner was excellent highly recommended
Location:
great location in the middle of downtown chicago
amazing location couldn’t beat it
this property was in a great location
great location but you really need to fix the plumbing
great location close to lots of shopping the theater great food and all the museums and parks
Read more reviews
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4. Lovely apartment in central Hyde Park (from USD 136)

Likely to appeal to those who want to spend their days in central Hyde Park, this lovely apartment is a perfect base to explore the surrounding neighborhood rich with eclectic shops, restaurants, and historic sites. You can easily take a stroll on foot or bike to the cultural district and Lakefront Trail.

When staying indoors, feel free to snuggle up on the sofa and fill the cozy space with music from the vinyl record player or switch on the smart TV and tune in to your favorite streaming shows. WiFi is made available to enable your online viewing. There’s also a full-size kitchen for your meal preparations and a breakfast nook to comfortably savor your cooking. Featuring an expansive master suite with a queen-size bed and sizeable windows, you’ll be able to wake up to gorgeous views of Hyde Park.

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381 meters (0.3 ft) from Museum of Science and Industry, Chicago
4 reviews   Wifi Available
Apartment 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 5 days before check-in.

Top guest reviews
Cleanliness:
the building is clean and modern with a door person
it was clean and exactly as shown in photos
very clean and organized place area was really classy and had a nice vibe to it
there was a drawer with utensils and blankets/towels were all super clean
bed room and bathroom was very clean comfy bed and nice view in the morning
Location:
the location was really close to the lake which was awesome
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5. Large and acclaimed mansion near Montrose Beach (from USD 1150)

This huge acclaimed mansion near Montrose Beach is the ideal lake getaway in Chicago with your extended family. It spotlights 9 distinct bedrooms with double and queen-size beds so there’s surely enough space for 21 guests. You and your crew have two living rooms equipped with smart TVs, high-speed WiFi, and a pool table to enjoy during your idle hours. The fully equipped kitchen allows your group’s cooks to prepare and serve delectable dishes buffet style. For outdoor cooking and leisure, there’s an expansive yard with a grill and seating at your disposal.

The property also has a wide parking space for five vehicles if you plan to arrive by car. But in terms of sightseeing, you can easily walk to the area’s nearby hotspots as it is only a few blocks away from Lake Michigan and Wrigley Field.

Stayed at this property?
Chicago, Illinois, United States
20.2 km (12.6 mi) from Museum of Science and Industry, Chicago
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
Cleanliness:
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
Host:
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
Location:
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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6. Cozy condo unit in Lake View East neighborhood (from USD 268)

Located in the neighborhood of Lake View East, this cozy condo vacation rental in Chicago puts you close to all the bustling areas of the lakefront and Lincoln Park where you can hit the beach, run, and bike. You can also explore the wide range of coffee shops, bars, and restaurants to end your days with local flavors at a local joint. But for days when you want to enjoy your cooking, the condo’s equipped kitchen has got you covered. The living room is appointed with a fireplace, WiFi, and 60-inch smart TV, and the dining area is designed for six persons.

There are two bedrooms to while away the night but be sure to call dibs on the one with a separate tub if you’re keen to have your soaking rituals. Alfresco relaxation is also possible in the shared back deck.

Stayed at this property?

16.63 km (10.4 mi) from Museum of Science and Industry, Chicago
43 reviews   Wifi Available
condo 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 5
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the apartment was perfect for the four of us (including our 7 year old twins)
Cleanliness:
this place was fabulous the condo is so clean and well appointed
the condo is extremely comfortable and spotlessly clean and in a quiet and very smart avenue
we enjoyed the property it’s was clean and nicely staged
most importantly their condo is spacious clean extremely well equipped and very comfortable
everything was great clean home and friendly owners
Host:
jeff was a perfect host
third your hosts are hospitable attentive to questions and needs and just very nice people
jeff was an excellent host
the owner was very responsive and checked in often to see if we needed anything
the owners have great taste and have truly thought of every little thing that makes a stay comfortable
Location:
second the location is the ideal neighborhood
great property/location - super quiet spot - convenient to many restaurants shopping groceries
we did everything so easily from this location
it is a great place to stay in a great neighborhood
walk to wrigley the l lincoln park great restaurants and coffee in a super location
Read more reviews
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7. Family-friendly apartment near Loyola University (from USD 323)

For those who are looking for a kid-friendly property, this second-floor apartment with amenities such as a travel crib, high-chair, children’s tableware, and outlet covers is the one to book for the family. The spacious property has a 55-inch smart TV, complimentary WiFi, and cable services to cater to your entertainment needs. As for meal preparations, you will be delighted in the fully equipped kitchen when cooking your delicious recipes. There is also an enclosed back porch and a large front balcony for relaxing while taking in the metropolitan views.

The property offers discounts for seven-night stays or more and has paid on-street parking in accordance with city law. It is located two blocks from Loyola University and Hartigan Beach Park. Also, the host couple lives on the first floor and can promptly address concerns during your stay.

Stayed at this property?
Chicago, IL, US
24.47 km (15.3 mi) from Museum of Science and Industry, Chicago
Apartment 6 Guests 3 Bedrooms 2 Bathrooms
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8. Clean and well-maintained flat in North Kenwood

A clean and updated accommodation in the historic North Kenwood, this spacious two-level dwelling has the necessary amenities for a convenient stay. As soon as you enter the main floor, you’re immediately welcomed with a view all the way through to the back of the home, thanks to its open-concept interiors and lots of windows. Flat-screen TVs are appointed in every room and reliable WiFi is made available throughout the property. The formal dining area is also a great space for family occasions. Its second level tucks three gorgeous bedrooms with queen and king-size beds.

For your parking needs, your booking readily comes with free on-street parking. And if you’re set to do an all-day excursion, you may want to plan your day ahead as there are several nearby places to visit including Hyde Park and Lake Michigan.

Stayed at this property?
Chicago, IL, US
2.9 km (1.8 mi) from Museum of Science and Industry, Chicago
townhome 6 Guests 3 Bedrooms 2 Bathrooms
Oops, this listing is currently inactive. Check out these alternative properties in the same location.
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Chicago: a city of sheer awesomeness

Chicago will forever be a city of sheer awesomeness since it is the home of the famous Chicago Lakefront facing Lake Michigan, the famous Field Museum, great pizza places, and the legendary speakeasies of the Prohibition era. As a result, Chicago is indeed a vacationer’s paradise. Here are some of the best lakefront Vrbo accommodations in Chicago. All you have to do now is select one of these awesome bookings, rent today, and the beautiful sights, sounds, smells, and tastes of Chicago will all be yours to savor and enjoy!

Stayed at this property?

Frequently asked questions about Vrbo vacation rentals near the Chicago Lakefront, Illinois

1. Which Vrbo vacation rentals near the Chicago Lakefront are suitable for families?

This stone mansion with a hot tub, this lake-view penthouse with gym and club room, and this penthouse apartment with city views are some top family-friendly Vrbo rentals near the Chicago Lakefront.

2. Which Vrbo vacation rentals near the Chicago Lakefront have parking?

Some of the best Vrbo rentals with parking available for guests’ convenience include this large and acclaimed mansion near Montrose Beach and this cozy condo unit in Lake View East neighborhood.

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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A budding historian, author, and gamer. Doing freelance writing while finishing his graduate studies.

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