10 Best Vrbo Vacation Rentals In Chicago Old Town, Illinois - Updated 2021

vrbo chicago old town
Deepa
Deepa
Updated

Old Town is Chicago’s one of the most historic districts. It is known for its lovely Victorian-era architecture, tree-lined streets and is home to St. Michael’s Church, one of the seven buildings to survive the Great Chicago Fire in 1871. You will also find eclectic coffee shops, quirky boutiques, mom and pop shops, and charming eateries around every corner of the town. Though this town is cocooned away from the hustle and bustle of downtown Chicago, there is plenty to enjoy within walking distance. Lincoln Park Zoo, North Avenue beach, The Second City theater, Oak Street, and Michigan Avenue can be reached by walk. There are over 103 restaurants in and around the town, bars and lounges are abundant on Wells and Magnificent Mile is home to numerous shops. If you are in Chicago and are looking for a place to stay, the Old Town should be your best bet. Here are the best Vrbo accommodations in Chicago Old Town, Illinois.

1. Three-level accommodation with sunroom (from USD 687)

Booking is done for the entire house that features five bedrooms, two kitchens, three bathrooms, and a half-bath. This three-level, pet-friendly house can accommodate 24 people and is perfect for a large group or family. It is located in a quiet neighborhood and is at walking distance from downtown, beach, park, restaurants, and bars. It has two connected floors and one autonomous level on the first floor. Both its kitchens are fully stocked and have a stove, oven, dishwasher, and microwave. There are two sets of washers and dryers. Air conditioning and central heating are provided. There is a detached garage where the guests can park up to three cars.

Huge 5 BR Home * Private Yard * Walk Everywhere * Parking for 3 Cars
15 reviews
House 5 Bedrooms 4 Bathrooms
Top guest reviews
Amenities & Room:
was the traffic in front of the house
Loved having the separate garden apartment with its own kitchen
It included anything we needed for our stay
Everything was clean comfortable and easy to use and lots of room to unpack and make ourselves at home
Couches are a bit uncomfortable as they are futons to accommodate more sleeping room
Cleanliness:
The house was quite large
The house is a little older but very clean with lovely decor and there is absolutely everything you need there
The house was nice and well stocked and the beds were very comfortable
Host:
she came and greeted us and helped us with many suggestions
She allowed us to decorate which set the mood for our get together
The home is lovely and well maintained
Property manager was super responsive and helpful letting us check in early and monitoring all our needs Only part we found challenging
Our party was reduced drastically and we never even entered the downstairs unit as it had a separate door and lock Inna was very very nice
Location:
just a few blocks away
when the private school across the way gets out just be mindful if you are coming and going around 3pm Super location and easy for numerous guests
The house has amazing character and is in such a perfect location on a nice quiet residential street; we were able to easily walk to the train which got us to Wrigley Field and also to downtown
The owner responded to every question within minutes
The train is close by but within a day everyone was quite used to the noise
Read more reviews

2. Warehouse-turned house on Chicago's newest neighborhood (from USD 369)

This warehouse turned costume factory turned bright and sunny 1800-square feet (167.2 square meters) loft can accommodate up to 10 guests. It is located in Chicago’s latest neighborhood, ‘SoNo’, at the juncture of River North and Lincoln Park-Old Town. Free parking on the street and off-street parking spaces are available too. This property is just two blocks from the Red Line train, provides easy access to three bus routes and to the Kennedy and Lake Shore Drive Expressways. Restaurants, shops, brewery, grocery stores, pubs, wine bars, food courts, theatres are all close by.

Spacious Bright & Spotlessly Clean in the Heart of Everything Chicago - Covid Clean
107 reviews
condo 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The kitchen isn't done justice in the pictures online
Very spacious with plenty of room
The beds were comfortable and plenty of hot water
The condo had lots of space and was very comfortable
We could not believe the size of the kitchen-
Host:
Our host was very responsive
improve theater Owner had great recommendations for things to do
All her helpful suggestions for area attractions restaurants
Spacious immaculate and well equipped
The property was huge extremely clean and well appointed
Location:
A short Uber into the city for site seeing and
There were plenty of restaurants and grocery stores within walking distance
the Magic Factory was a great location with groceries and restaurants within walking distance
5 min walk away Close to IO
The location was perfect too Easy parking and close to everything
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3. A luxurious abode with baby gear (from USD 724)

This newly renovated, luxurious home is located on the first floor of a free-standing house. It is in the heart of the Historic Old town triangle on a quiet, tree-lined, and secluded street. The property is at walking distance from Wells Street that is home to several restaurants, the Second City - a premium comedy club, coffee shops, fine dining, workout facilities and shops, Lincoln Park Zoo, Lake Michigan, and Brown Line bus route. Guests are provided two bicycles to explore the city. Complimentary guest parking permits are available. Amenities include linens, bathrobes, towels, washers, and dryers, Essential baby gear (high chair, pack and play with mattress and linens, baby bath, etc.) are available upon request. A weekly housekeeper is included in stays over 10 days.

Opulent 3bdr2bth Old Town Luxury + Parking prmts
36 reviews
House 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
Wonderful apartment in Old Town
Inside everything is done to a very high standard
The beds were very comfortable
The luxury kitchen was well stocked and
a joy to use The bedrooms and living area were beautiful
Cleanliness:
The place is exactly as pictured and very clean
and it's been kept extremely clean
The apartment was beautifully decorated
Everything was just as explained and more
Host:
They accommodated us when our flight home was delayed
First of all Veronica was extremely responsive to messages and providing detailed clear instructions
Wow Such a beautiful well appointed home
fruits veggies and dips
It had everything we needed and the hosts were immediately responsive to any of our questions
Location:
Great location in a beautiful neighborhood
It is situated in a quiet neighborhood just a few blocks from many good restaurants coffee shops and
You are just blocks away from Second City and lovely restaurants and shops
The neighborhood is quiet but a only a few blocks from everything you want
We stayed for a week in December and enjoyed easy walks to coffee shops bars restaurants and attractions including the Second City Comedy Club a few minutes away
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4. Large house with a front yard and grill (from USD 599)

This 3000 square-feet (278.7 square meters) three-story house, located on a quiet neighborhood street in Chicago’s historic east Old Town, is perfect for a group or family. It is at walking distance from downtown, beach, cafes, park, restaurants, grocery stores, and bars. This house features two private outdoor spaces, free parking in a detached garage, and a spacious fully fenced front yard with grill. Amenities include washer, dryer, air conditioning, and central heating, and a large fully-stocked kitchen with stove, oven, dishwasher, and microwave. The first floor has a living room with a high ceiling and a fireplace, a dining room, a full bath, and a kitchen. The second floor has two bedrooms and one full bathroom. And, the third floor has a large bar with a full-size refrigerator and a microwave, family room and two bedrooms with an en-suite bath each. There is a deck off one of the bedrooms. Pets are welcome too!

Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
22 reviews
House 4 Bedrooms 4 Bathrooms
Top guest reviews
Amenities & Room:
All the bedrooms are up one or two flights of stairs
Some towels need to be replaced
We all had enough space for private sleeping and relaxing yet were able to gather comfortable in the main living/dining area
the bedrooms are large and have great en suite bathrooms off the two masters on the top floor
It was inexpensive and while there is theoretically free parking right out front
Cleanliness:
House and linens were very clean
Inna's house was huge with 4 bedrooms and 4 bathrooms
Host:
Inna was an amazing host Very easy going and responsive to our needs
We had 16 girls in our group First of all
All the beds were made up and ready for our group as they arrived Inna met us on the first night and checked up on us through the 5 night stay
The host is very responsive and helpful I would highly recommend this home
Inna was very good about getting back to us when we had a question
Location:
There are lots of places to eat within easy walking distance
The location was only a couple minute walk from the brown line spot and was convenient to travel to downtown
Such a great location near the El and Old Town restaurants and shops Easy to park
The train groceries and restaurants are all within easy walking distance
beach- also a walk away during the day
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5. Apartment with plenty of desk space (from USD 121)

This apartment is located in Chicago’s Old Town. It is close to restaurants and shopping centers and is a short walk from Sedgwick station. It is perfect for someone who is on a working vacation. There are plenty of desk spaces in the house. This house features exposed-brick walls, large beautiful windows, and a spacious living area. Amenities include high-speed internet, heater, air conditioning, washer, dryer, a complimentary Roku streaming device, and more than 40 basic HD channels. It is perched up on the fourth floor and is accessible only through stairs. Paid street parking or a nearby paid parking lot is available.

Sonder | North Wells | Spacious 2BR
9 reviews
Apartment 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
Plenty of room to spread out in this centrally located Old Town apartment with tons of light (roof windows)
Cleanliness:
very clean and spacious Location was perfect too
Host:
Plenty of parking coffee drinks and food in every direction
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6. Plush lodging with a modern, fully equipped kitchen (from USD 181)

This house, located in the Old Town, has a bright and cozy living area with beautiful expansive windows, spacious bedrooms with comfortable beds, and modern fully equipped kitchen with updated appliances. There are plenty of desk spaces in the house. Amenities include high-speed internet, heater, air conditioning, washer, dryer, satellite TV, refrigerator, stove, dishwasher, oven, and coffee maker. Pets are not allowed.

Sonder | North Wells | Chic 3BR
20 reviews
Apartment 3 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
the water in the shower took at least five solid minutes to heat up
the one for the front was not only deafeningly loud
The only drawbacks to the apartment were: somewhat tricky shallow winding stairs (no elevator);
but it did not cool the two front bedrooms much at all
The bedroom off the kitchen stayed nice and cool Fixes to the AC and the water heater would make this place amazing; as it stands we still loved staying there
Host:
Very nice new place Exceptionally easy to find Fun neighborhood
Pretty good Only issues are street noice and the fact that all three bathrooms are outside the bedrooms
Checking in and out could not have been easier
Good communication with property manager about how to enter & exit the place Noisy late at night on Fridays & weekends because of the local bars
We had a family reunion
Location:
Good location walking distance to restaurants shops
Chicago Enjoyed the neighborhood and the building
On the other hand lots of local bars & other places to eat
There was an upscale grocery store a few blocks away Easy to get to downtown either via bus nearby (N LaSalle Dr) or taxi
The neighborhood was great with plenty of restaurants and young families out with strollers at night (which means "safe" to me)
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7. Cozy home with a deck that offers a skyline view (from USD 85)

This two-bedroom house is located between Twin Anchors Restaurant and Old St. Michael’s Church. It has a front yard as well as a back yard and is at walking distance from beach, restaurants, pharmacies, theatres, and groceries. The backyard is a perfect spot for families, children and pets to unwind. Guests can view the downtown skyline from the top deck. Lincoln Park Zoo, North Avenue Beach (known for volleyball, swimming, and biking), and Michigan Avenue are also close by.

Cozy apartment in Old Town Triangle
29 reviews
Apartment 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The bed is quite comfortable - an important feature
I came with my mom and 2 children (ages 7 and 9)
Had a great 2 night stay
Two large but well-behaved dogs live upstairs - be aware you will hear paw-steps above in the morning and an occasional bark
Good bar right down the street in Twin Anchors Would return
Cleanliness:
I recently stayed at the apartment for 4 nights and found it to be clean and comfortable and exactly as represented
Had a few hiccups checking in
It is clean; the beds are very comfortable; the neighborhood is safe and quiet
Host:
responsive considerate and generous
We felt very safe Lisa was so friendly and accommodating
Lisa was very accommodating and helpful
Lisa was exceptionally responsive during the the booking process and was very easy to communicate with during the check-in and stay
Lisa was very accommodating and responsive
Location:
Plus the the entire city of Chicago is easily accessible by L or by bus
There are many restaurants and activities within walking distance
it is walking distance from numerous restaurants bars
Just a short Uber ride to Navy Pier Wrigley Field and Magnificent Mile
The garden apartment is in a great neighborhood
Read more reviews

8. Penthouse with Jacuzzi and rooftop deck (from USD 160)

This beautiful, 4,000 square-feet (371.6 square meters) penthouse loft was built in 1897 and completely renovated in 2016. It is located next to the ‘Magnificent Mile’. Its high ceilings, exposed brick walls, vintage front doors, 120-year-old barn wood floors will remind you of the yesteryears. The rooftop deck overlooks Willis (Sears) Tower. It is at walking distance from restaurants, comedy clubs (Zanies and the Second City), theaters, boutique shopping, public transportation (Red Line, and 156 bus line), bars and beach. It comes with five bedrooms, four full bathrooms (Jacuzzi in a couple of them), two full kitchens, two full laundry rooms, and two full living rooms. Extra amenities include two push-button fireplaces, vintage 1950 first coin-operated Valley pool table, and a dartboard.

Downtown Chicago Penthouse *Private Roof Top* Pet-Friendly
2 reviews
condo 5 Bedrooms 4 Bathrooms
Top guest reviews
Amenities & Room:
It felt like they were waiting outside for us
It felt like we were within walking distance of anything we wanted to do
Location:
Loved loved loved this place
Read more reviews

9. Two-bedroom flat with a grill in the backyard (from USD 99)

This spacious two-bedroom apartment is located on a quiet neighborhood street in the Old Town. It features a large living room with dining space, a compact kitchen with a stove, oven, microwave and refrigerator and a full bath. Guests also have access to the backyard with a grill. Amenities include free parking on premise, washer, dryer, air conditioning, and central heating. It is a pet-friendly property.

Gold Coast-Old Town Gem with Parking~ Bring Family or Friends~Heart of Chicago
9 reviews
Apartment 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
great kitchen spacious living room
It is cozy and comfortable enough
All furniture is brand new
Cleanliness:
Location was great Apartment was clean
Host:
Whenever I had a question she would get right back to me and was so helpful and nice about everything
The owner responded to all questions within minutes
Convenient locale and a very communicative landlord made our stay in Chicago for a family wedding seamless
so thats a nice touch
We weren't able to get in the garage when we arrived and we called the owner and Inna came right over and took care of
Location:
Also everything else was a very short Uber or train ride away
So many places to eat and go to that was walking distance
perfect bathrooms and parking Also amazing location
We enjoyed coffee on the patio in the morning and sitting out in the evening just to talk
It was great being so close to Wells street and the the train was only a few minute walk away
Read more reviews

10. Large house with rooftop terrace (from USD 362)

This apartment, located in the Old Town, has a beautiful open-concept living area, expansive windows, a fully equipped kitchen, and a spacious rooftop terrace with sitting area. It has several desk spaces and provides high-speed internet among other amenities. Cafes, restaurants, shops, subway are just a few minutes away from the property. Paid parking options are available nearby. This house is on the second floor and is accessible only through stairs.

Sonder | Burton Place | Stunning 4BR + Rooftop
13 reviews
Apartment 4 Bedrooms 4 Bathrooms
Top guest reviews
Amenities & Room:
the bedrooms are most comfortable and the rooftop patio was a special treat
black out blinds in the bedrooms Thank you
The thermostats is on the main floor it would just cook the bedrooms on the top two levels
Our only complaint was the temperature of the space
Location A+ Nice open floor plan for our group Liked seperate floors for bedrooms Loved outside space
Host:
We will definitely return However please get
We just opened some windows & the problem was solved
This is our first experience with Sonder
was our inability to find a sink drain cover
and you exceeded our (already lofty) expectations About the "worst" thing that happened
Location:
Great location can walk to many Chicago activities Called Sonder a couple of times for assistance with heat & to get more paper supplies
Check in & out procedures were very easy
We celebrated my daughter's 30th and couldn't have asked for a better condo The location is perfect close to everything you could want and a quick Uber ride for anything else
But there are plenty options just walking out the door
A couple of suggestions Please add a hair dryer to each bath
Read more reviews

Walk to everything Chicago has to offer from Old Town

These Vrbo accommodations are located at prime locations in Chicago Old Town. They are at walking distance from all of the main attractions in Chicago and are also situated close to subway and bus stations. Enjoy your stay and explore the city at ease while making beautiful memories.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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