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 October 25, 2025.
1. Stone mansion with a hot tub
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.
Chicago, Illinois, United States
17.28 km (10.8 mi) from Museum of Science and Industry, Chicago
2. Lake-view penthouse with gym and club room
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.
Chicago, Illinois, United States
12.42 km (7.8 mi) from Museum of Science and Industry, Chicago
3. Penthouse apartment with city views
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).
Chicago, Illinois, United States
11.15 km (7.0 mi) from Museum of Science and Industry, Chicago
Top guest reviews
Host:
host was extremely easy to communicate with and accommodatingthe communication with the owner was excellent highly recommendedLocation:
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 parksRead more reviewsCleanliness:
the apartment was very nice and cleanfirst time i go to chicago the penthouse is beautiful clean i liked it a lot and my family
4. Large and acclaimed mansion near Montrose Beach
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.
Chicago, Illinois, United States
20.18 km (12.6 mi) from Museum of Science and Industry, Chicago
Top guest reviews
Host:
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 hadLocation:
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 somethingCleanliness:
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 postedRead more reviewsAmenities & 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 meal
5. Cozy condo unit in Lake View East neighborhood
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.
Chicago, Illinois, United States
17.45 km (10.9 mi) from Museum of Science and Industry, Chicago
Top guest reviews
Host:
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 comfortableLocation:
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 locationCleanliness:
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 ownersRead more reviewsAmenities & Room:
the apartment was perfect for the four of us (including our 7 year old twins)
6. Family-friendly apartment near Loyola University
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.
Chicago, IL, US
24.47 km (15.3 mi) from Museum of Science and Industry, Chicago
7. 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
8. Superior apartment at the Plymouth
This apartment at the Plymouth is really superior to the rest because it can accommodate a group of eight in its four comfortable and spacious bedrooms, each with a double bed. Three fully equipped and luxurious bathrooms are also present, as well as a complete kitchen with dining area. Also, the unit comes with self-check in so coming in from the airport will be a breeze. Also, the unit is very near the famous tourist attractions of Chicago since it is at the city center. As a result, if you do not mind the city noise, this apartment at the Plymouth is indeed for you!
10.27 km (6.4 mi) from Museum of Science and Industry, ChicagoTop guest reviews
Host:
so Sonder is good companyThey did make amends with the dirty sheets and a one other itemGood overall Property management staff responsive to our arrival Suggest more seating in combo kitchen/den areaLocation:
but it is really bad at nightAlso the neighborhood is quite loud at nightJust beware of little beds and loud night time neighborhoodTo seat 4 of us we used the hallway settee Could use another comfortable chair Tile shower floors were slippery when wet used a face cloth to stand on Bedside wall lamp in 1stCleanliness:
Showers had great water pressure and plenty of hot waterVery clean comfy bedsFaucet in kitchen was loose and wasn't able to get hot waterRead more reviewsAmenities & Room:
bedroom off kitchen was looseAll the beds are doubles so not sure about sleeping 2 in each they are quite short bedsEasy access to the unit Will definitely stay again
9. Comfortably modern unit
This comfortably modern condo unit is a great place for a group of six business travelers to stay in for it has two bedrooms with comfortable beds. There are also two complete bathrooms which exceed local cleanliness standards as well as a kitchen with microwave and dishwasher. Also, the unit is very near the famous conference centers of Chicago, especially the McCormick Conference center. After the conference, business travelers can visit the Fields Museum and the local parks to relax since the condo is just nearby. There are also many local restaurants to eat in and grocery stores for you to stock up your larder. Thus, for business travelers, this condo is the best place for you to stay!
Chicago, IL, US
9.32 km (5.8 mi) from Museum of Science and Industry, ChicagoTop guest reviews
Host:
owner seemed very niceLocation:
we came for a conference at mccormick and it was the perfect place business travelers delightCleanliness:
apartment is immaculately clean and well stockedoverall was a really good stay condo was clean but not immaculatecarmen has an amazing place very clean and comfortable with unforgettable viewsRead more reviewsAmenities & Room:
little touches (fancy room spray in the bathroom edison bulb lamps for evening lighting) were appreciated
10. Beautiful apartment in the heart of Chicago
This beautiful apartment in the heart of Chicago is the place to stay because it can accommodate a group of six in its two bedrooms, both with queen-sized beds. There are also two complete bathrooms as well as a complete kitchen with spacious and beautiful dining area. Also, the unit is new so you can be assured of a comfortable and fun experience. There is also wireless internet and cable TV. The building also has a swimming pool, hot tub, and fitness center so you can also take care of your health. The apartment building is also very close to the attractions of Chicago, including the parks, museums, and Lake Michigan. As a result, this apartment is best for those who truly want to enjoy Chicago at its finest.
1000 S Clark St
9.53 km (6.0 mi) from Museum of Science and Industry, Chicago
11. Chic and comfortable flat
This comfortable apartment is a great place to stay for a squad of eight since it has four comfortable and roomy bedrooms as well as three complete bathrooms. The kitchen is fully equipped with the most important appliances and there is cable TV and high-speed wireless internet available. The building also has an amazing rooftop lounge which has a grill for those who want to enjoy a little cookout. However, even though it has all the modern conveniences of a modern home, this apartment unit has preserved the mid-century vibes of the original building. As a result, this apartment is indeed perfect for large groups, and even families, vacationing together.
417 S. Dearborn
10.27 km (6.4 mi) from Museum of Science and Industry, Chicago
12. Colorful flat in the South Loop
This colorful apartment in the South Loop of Chicago is an amazing place for couples to stay because its single bedroom has a queen-sized bed and it also has a complete and well-equipped bathroom. There is also a complete kitchen with a dining area perfect for romantic dinners. Also, there is cable TV, wireless internet, and all other amenities that will make your stay in Chicago more comfortable. For those who still have work to do, there is a desk space provided for your working needs. Being in the South Loop, this apartment is in close proximity to the best local restaurants, pizzerias, and even the Field Museum. As a result, this is a great place to stay for a romantic getaway in Chicago.
9.29 km (5.8 mi) from Museum of Science and Industry, ChicagoTop guest reviews
Read more reviewsHost:
Very cozy and decorated nicely Excellent south loop location very close to the EL and many other popular tourist attractions
13. Spacious condo in downtown Chicago
This spacious condo in downtown Chicago is perfect for a group of seven because it has three spacious and comfy bedrooms, each with a king-sized bed. Also, there are two complete bathrooms, a full-size complete kitchen, and a large dining area. There are also laundry facilities, wireless internet, and cable TV. The condo is also very near the attractions of Chicago like the Millennium Park, Navy Pier, and Shedd Aquarium. If you want to stay in Chicago for a long time, either as a long-term visitor or as a student, this unit is available for long-term rentals, as long as you remember to not make too much noise. As a result, this spacious condo in downtown Chicago is for anyone and everyone who is looking for a good time in Chicago!
Chicago, IL, US
14. Lovely apartment in central Hyde Park
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.
381 meters (0.3 ft) from Museum of Science and Industry, ChicagoAccommodates: 3
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 5 days before check-in.
Top guest reviews
Location:
the location was really close to the lake which was awesomeRead more reviewsCleanliness:
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 morning
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
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