12 Best Vrbo Vacation Rentals Near Chicago Lakefront, Illinois - Updated 2022

vrbo chicago lakefront

Chicago is well-known as the Windy City due to its windy weather and as the home of Chicago deep-dish pizza but it also has many other attractions. These include the famous 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. Book one among the best Vrbo accommodations near the Chicago Lakefront, Chicago, Illinois, and the secrets of Chicago will be yours to learn.

1. Top-floor penthouse apartment with city views (from USD 593)

Experience downtown 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, the modern unit 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).

Modern 3BR Penthouse in the Loop | Roof Deck
11 reviews  Wifi Available
Apartment 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
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 was extremely easy to communicate with and accommodating
the communication with the owner was excellent highly recommended
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

2. 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.

UChicago, Lake, Sci Museum with Gym + W&D | Zencity
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
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
the location was really close to the lake which was awesome
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3. Large and acclaimed mansion near Montrose Beach (from USD 1123)

This huge acclaimed mansion near Montrose Beach is the ideal hideaway for a Chicago escapade 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.

Beautiful 9Br Mansion w/ 4 Parking Spots. Walk To Wrigley Field & Lake Michigan!
Chicago, Illinois, United States
89 reviews Premier Host  Wifi Available
Private vacation home 21 Guests 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
Read more reviews

4. Cozy condo unit in Lake View East neighborhood (from USD 268)

Located in the neighborhood of Lake View East, this cozy condo unit 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 own 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.

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)
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
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
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
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5. 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.

Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
Chicago, IL, US
Apartment 6 Guests 3 Bedrooms 2 Bathrooms

6. 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.

Historical Home Built 1893, In Historic North Kenwood
Chicago, IL, US
townhome 6 Guests 3 Bedrooms 2 Bathrooms

7. 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!

Sonder | The Plymouth | Superior 4BR + Gym
4 reviews
Apartment 8 Guests 4 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
bedroom off kitchen was loose
All the beds are doubles so not sure about sleeping 2 in each they are quite short beds
Easy access to the unit Will definitely stay again
Showers had great water pressure and plenty of hot water
Very clean comfy beds
Faucet in kitchen was loose and wasn't able to get hot water
so Sonder is good company
They did make amends with the dirty sheets and a one other item
Good overall Property management staff responsive to our arrival Suggest more seating in combo kitchen/den area
but it is really bad at night
Also the neighborhood is quite loud at night
Just beware of little beds and loud night time neighborhood
To 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 1st
Read more reviews

8. 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!

Modern Condo, close to everything!
Chicago, IL, US
5 reviews
condo 6 Guests 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
little touches (fancy room spray in the bathroom edison bulb lamps for evening lighting) were appreciated
apartment is immaculately clean and well stocked
overall was a really good stay condo was clean but not immaculate
carmen has an amazing place very clean and comfortable with unforgettable views
owner seemed very nice
we came for a conference at mccormick and it was the perfect place business travelers delight
Read more reviews

9. 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.

Welcome To The Heart Of Chicago's Great Culture (Museums, Parks, Lakefront )
1000 S Clark St
50 reviews
Apartment 6 Guests 2 Bedrooms 2 Bathrooms

10. 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.

Plymouth Tavern Apartment
417 S. Dearborn
1 review
Apartment 8 Guests 4 Bedrooms 3 Bathrooms

11. 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.

Sonder | Roosevelt Suites | Vibrant 1BR
2 reviews
Apartment 2 Guests 1 Bedroom 1 Bathroom
Top guest reviews
Very cozy and decorated nicely Excellent south loop location very close to the EL and many other popular tourist attractions
Read more reviews

12. Spacious condo in downtown Chicago

spacious condo in downtown chicago
Source: Vrbo

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!

*Walk to Everything* Magnificent Mile* Navy Pier*Shedd Aquarium* Millennium Park
Chicago, IL, US
7 Guests 3 Bedrooms 2 Bathrooms

Chicago: a city of sheer awesomeness

Chicago, which is popularly known as the Windy City, 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, Chicago deep-dish pizza, and the famous speakeasies of the Prohibition era. As a result, Chicago is indeed a vacationer’s paradise. Here are some of the best Vrbo rentals in the Chicago Lakefront in the city of 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!

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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