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 412)
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 2 CarsAccommodates: 24
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Amenities & Room:
was the traffic in front of the houseLoved having the separate garden apartment with its own kitchenIt included anything we needed for our stayEverything was clean comfortable and easy to use and lots of room to unpack and make ourselves at homeCouches are a bit uncomfortable as they are futons to accommodate more sleeping roomCleanliness:
The house was quite largeThe house is a little older but very clean with lovely decor and there is absolutely everything you need thereThe house was nice and well stocked and the beds were very comfortableHost:
she came and greeted us and helped us with many suggestionsShe allowed us to decorate which set the mood for our get togetherThe home is lovely and well maintainedProperty manager was super responsive and helpful letting us check in early and monitoring all our needs Only part we found challengingOur party was reduced drastically and we never even entered the downstairs unit as it had a separate door and lock Inna was very very niceRead more reviewsLocation:
just a few blocks awaywhen 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 guestsThe 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 downtownThe owner responded to every question within minutesThe train is close by but within a day everyone was quite used to the noise
2. Warehouse-turned house on Chicago's newest neighborhood (from USD 360)
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 CleanAccommodates: 10
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Amenities & Room:
The kitchen isn't done justice in the pictures onlineVery spacious with plenty of roomThe beds were comfortable and plenty of hot waterThe condo had lots of space and was very comfortableWe could not believe the size of the kitchen-Host:
Our host was very responsiveimprove theater Owner had great recommendations for things to doAll her helpful suggestions for area attractions restaurantsSpacious immaculate and well equippedThe property was huge extremely clean and well appointedRead more reviewsLocation:
A short Uber into the city for site seeing andThere were plenty of restaurants and grocery stores within walking distancethe Magic Factory was a great location with groceries and restaurants within walking distance5 min walk away Close to IOThe location was perfect too Easy parking and close to everything
3. A luxurious abode with baby gear (from USD 546)
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 prmtsAccommodates: 4
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.
Top guest reviews
Amenities & Room:
Wonderful apartment in Old TownInside everything is done to a very high standardThe beds were very comfortableThe luxury kitchen was well stocked anda joy to use The bedrooms and living area were beautifulCleanliness:
The place is exactly as pictured and very cleanand it's been kept extremely cleanThe apartment was beautifully decoratedEverything was just as explained and moreHost:
They accommodated us when our flight home was delayedFirst of all Veronica was extremely responsive to messages and providing detailed clear instructionsWow Such a beautiful well appointed homefruits veggies and dipsIt had everything we needed and the hosts were immediately responsive to any of our questionsRead more reviewsLocation:
Great location in a beautiful neighborhoodIt is situated in a quiet neighborhood just a few blocks from many good restaurants coffee shops andYou are just blocks away from Second City and lovely restaurants and shopsThe neighborhood is quiet but a only a few blocks from everything you wantWe 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
4. Large house with a front yard and grill (from USD 292)
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 LocationAccommodates: 21
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Amenities & Room:
All the bedrooms are up one or two flights of stairsSome towels need to be replacedWe all had enough space for private sleeping and relaxing yet were able to gather comfortable in the main living/dining areathe bedrooms are large and have great en suite bathrooms off the two masters on the top floorIt was inexpensive and while there is theoretically free parking right out frontHost:
Inna was an amazing host Very easy going and responsive to our needsWe had 16 girls in our group First of allAll 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 stayThe host is very responsive and helpful I would highly recommend this homeInna was very good about getting back to us when we had a questionRead more reviewsLocation:
There are lots of places to eat within easy walking distanceThe location was only a couple minute walk from the brown line spot and was convenient to travel to downtownSuch a great location near the El and Old Town restaurants and shops Easy to parkThe train groceries and restaurants are all within easy walking distancebeach- also a walk away during the day
5. Apartment with plenty of desk space
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 2BRTop 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 tooRead more reviewsHost:
Plenty of parking coffee drinks and food in every direction
6. Plush lodging with a modern, fully equipped kitchen
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 3BRTop guest reviews
Amenities & Room:
the water in the shower took at least five solid minutes to heat upthe one for the front was not only deafeningly loudThe only drawbacks to the apartment were: somewhat tricky shallow winding stairs (no elevator);but it did not cool the two front bedrooms much at allThe 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 thereHost:
Very nice new place Exceptionally easy to find Fun neighborhoodPretty good Only issues are street noice and the fact that all three bathrooms are outside the bedroomsChecking in and out could not have been easierGood communication with property manager about how to enter & exit the place Noisy late at night on Fridays & weekends because of the local barsWe had a family reunionRead more reviewsLocation:
Good location walking distance to restaurants shopsChicago Enjoyed the neighborhood and the buildingOn the other hand lots of local bars & other places to eatThere was an upscale grocery store a few blocks away Easy to get to downtown either via bus nearby (N LaSalle Dr) or taxiThe neighborhood was great with plenty of restaurants and young families out with strollers at night (which means "safe" to me)
7. Cozy home with a deck that offers a skyline view
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 TriangleTop guest reviews
Amenities & Room:
The bed is quite comfortable - an important featureI came with my mom and 2 children (ages 7 and 9)Had a great 2 night stayTwo large but well-behaved dogs live upstairs - be aware you will hear paw-steps above in the morning and an occasional barkGood bar right down the street in Twin Anchors Would returnCleanliness:
I recently stayed at the apartment for 4 nights and found it to be clean and comfortable and exactly as representedHad a few hiccups checking inIt is clean; the beds are very comfortable; the neighborhood is safe and quietHost:
responsive considerate and generousWe felt very safe Lisa was so friendly and accommodatingLisa was very accommodating and helpfulLisa was exceptionally responsive during the the booking process and was very easy to communicate with during the check-in and stayLisa was very accommodating and responsiveRead more reviewsLocation:
Plus the the entire city of Chicago is easily accessible by L or by busThere are many restaurants and activities within walking distanceit is walking distance from numerous restaurants barsJust a short Uber ride to Navy Pier Wrigley Field and Magnificent MileThe garden apartment is in a great neighborhood
8. Penthouse with hot tub and rooftop deck
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 (hot tub 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-FriendlyTop guest reviews
Amenities & Room:
It felt like they were waiting outside for usIt felt like we were within walking distance of anything we wanted to doRead more reviewsLocation:
Loved loved loved this place
9. Two-bedroom flat with a grill in the backyard
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 ChicagoTop guest reviews
Amenities & Room:
great kitchen spacious living roomIt is cozy and comfortable enoughAll furniture is brand newCleanliness:
Location was great Apartment was cleanHost:
Whenever I had a question she would get right back to me and was so helpful and nice about everythingThe owner responded to all questions within minutesConvenient locale and a very communicative landlord made our stay in Chicago for a family wedding seamlessso thats a nice touchWe weren't able to get in the garage when we arrived and we called the owner and Inna came right over and took care ofRead more reviewsLocation:
Also everything else was a very short Uber or train ride awaySo many places to eat and go to that was walking distanceperfect bathrooms and parking Also amazing locationWe enjoyed coffee on the patio in the morning and sitting out in the evening just to talkIt was great being so close to Wells street and the the train was only a few minute walk away
10. Large house with rooftop terrace
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 + RooftopTop guest reviews
Amenities & Room:
the bedrooms are most comfortable and the rooftop patio was a special treatblack out blinds in the bedrooms Thank youThe thermostats is on the main floor it would just cook the bedrooms on the top two levelsOur only complaint was the temperature of the spaceLocation A+ Nice open floor plan for our group Liked seperate floors for bedrooms Loved outside spaceHost:
We will definitely return However please getWe just opened some windows & the problem was solvedThis is our first experience with Sonderwas our inability to find a sink drain coverand you exceeded our (already lofty) expectations About the "worst" thing that happenedRead more reviewsLocation:
Great location can walk to many Chicago activities Called Sonder a couple of times for assistance with heat & to get more paper suppliesCheck in & out procedures were very easyWe 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 elseBut there are plenty options just walking out the doorA couple of suggestions Please add a hair dryer to each bath
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.
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