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.
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.
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).
Top guest reviews
Cleanliness:
the apartment was very nice and cleanfirst time i go to chicago the penthouse is beautiful clean i liked it a lot and my familyHost:
host was extremely easy to communicate with and accommodatingthe communication with the owner was excellent highly recommendedRead more reviewsLocation:
great location in the middle of downtown chicagoamazing location couldn’t beat itthis property was in a great locationgreat location but you really need to fix the plumbinggreat location close to lots of shopping the theater great food and all the museums and parks
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.
Top guest reviews
Cleanliness:
the building is clean and modern with a door personit was clean and exactly as shown in photosvery clean and organized place area was really classy and had a nice vibe to itthere was a drawer with utensils and blankets/towels were all super cleanbed room and bathroom was very clean comfy bed and nice view in the morningRead more reviewsLocation:
the location was really close to the lake which was awesome
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.
Top guest reviews
Amenities & Room:
nice dining area w/ large table to fit a large familyit looks just like the pictures with comfortable beds eclectic decor comfortable beds and lots of spacethe yard is perfect for a bbq with room for gamesthere's plenty of space for all to relax and gather in a lovely comfortable settingthe kitchen utensils were perfect to prepare a wonderful large family mealCleanliness:
the place was clean w/ nice featuresthe house itself was very clean and organizedthe house was very clean and well equippedthe house was clean throughout and overall quite charmingthe rooms were clean and looked exactly as the pictures postedHost:
the owners were excellent and treated us very wellthe owners were helpful with all questions we had and responded quicklythey were very accommodating and helpfulthe owner was very responsive to our needsana was a very gracious host and quick to respond to any questions we hadRead more reviewsLocation:
the location was golden for having fun downtownthe location offered a variety of restaurants and a great walk to montrose beachthe neighborhood is great to walk aroundit’s a beautiful house that’s walking distance to anything you’ll needloved that target/aldi were a quick walk incase someone forgot something
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.
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 appointedthe condo is extremely comfortable and spotlessly clean and in a quiet and very smart avenuewe enjoyed the property it’s was clean and nicely stagedmost importantly their condo is spacious clean extremely well equipped and very comfortableeverything was great clean home and friendly ownersHost:
jeff was a perfect hostthird your hosts are hospitable attentive to questions and needs and just very nice peoplejeff was an excellent hostthe owner was very responsive and checked in often to see if we needed anythingthe owners have great taste and have truly thought of every little thing that makes a stay comfortableRead more reviewsLocation:
second the location is the ideal neighborhoodgreat property/location - super quiet spot - convenient to many restaurants shopping grocerieswe did everything so easily from this locationit is a great place to stay in a great neighborhoodwalk to wrigley the l lincoln park great restaurants and coffee in a super location
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.
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.
Chicago, IL, US
2.9 km (1.8 mi) from Museum of Science and Industry, Chicago
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!
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.
History
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