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. Four-bedroom apartment near Lincoln Park Zoo (from USD 675)
This four-bedroom apartment offers guests a wonderful view of the city streets. It features three queen-sized beds and one king-sized bed, comfortably accommodating up to ten guests. There is also air conditioning, a smart TV, a travel crib, and various books for kids available. The clothes dryer and washing machine are available for guests who need to do some laundry. The private kitchen has all the basic appliances plus a coffee maker, so you’ll be able to prepare your own meals during your stay.
Conveniently, the home is not too far away from several notable locations as it’s only less than a mile (1.6 kilometers) away from Lincoln Park Zoo, John Hancock Center, Water Tower Place, and State Street.
Spacious & Clean/Full Floor Condo in HEART of Old Town/4Beds3BathsAccommodates: 10
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Amenities & Room:
a lovely apartment with all needed itemsCleanliness:
clean and beautiful property in a perfect spot bedrooms for allspacious clean comfortable beds and showersthe apartment was super clean and seemed even bigger in person than in the bookingHost:
property owner (michelle) was fantastic highly highly recommendcommunication with the owner michelle was quick and easyRead more reviewsLocation:
i was surprised how close it was to walk to lake michigan as welleasily walk to everything including the l trainsuper apartment great location and one of the best hosts we've experienced
2. Townhouse just a walking distance away from several attractions (from USD 496)
Boldly stating that it is the perfect relaxation destination for any traveler, this two-bedroom townhouse boasts having workspaces in both bedrooms, a beautiful kitchen, free parking on the premises, on-site laundry, and a convenient location. Some of its amenities include air conditioning, a TV, and a washing machine.
In terms of nearby locations, the townhouse is just a walking distance away from Wells Street, North Avenue, Lincoln Park, and the lakefront. It’s also just 1.1 mi (1.7 km) away from State Street, 1.4 mi (2.2 km) away from John Hancock Center, and 1.5 mi (2.4 km) away from Chicago Water Tower.
Charming & Bright Multilevel Townhome with ParkingAccommodates: 6
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Amenities & Room:
the dining table with seating for 6 made eating together such a treat the beds were very comfortableRead more reviewsLocation:
great location pleasant walk to old townhouse was located close to everything and was very comfortableanother bonus was having a parking space we couldn’t have dreamed of a better locationthe apartment is also walking distance from a good number of restaurants bars shops and lincoln park zoo
3. Three-bedroom house near downtown (from USD 299)
Located in a quiet neighborhood, this three-bedroom house offers ease of travel for its guests. It’s only a walking distance away from many notable locations around Chicago including downtown, the John Hancock Center, and Lincoln Park Zoo. This spacious house itself has five queen-sized beds that can sleep up to ten people.
The first-floor, open-plan living area is composed of the living room, kitchen, and dining room. This area is furnished with a fireplace, TV, standard kitchen appliances, various kids’ toys, and a washing machine.
Increíble 3 br en el casco antiguo con estacionamiento, Walk Score 96, ¡Qué descubrimiento!Accommodates: 10
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Amenities & Room:
main level kitchen/living room great upstairs beds simple but comfortableHost:
it was perfect for our needs and inna was extremely responsive any time i emailed herRead more reviewsLocation:
walking distance to mexican restaurant nail salon grocery store -fabulous
4. Three-bedroom house with a rear courtyard and garden (from USD 270)
From the title itself, this three-bedroom house offers a home-away-from-home experience for any traveler. It features hardwood and tiled floors alongside carpets and interior railings. There is a rear courtyard with a patio and garden where guests can relax while enjoying a nice drink. Inside, the home has a fireplace, TV, washing machine, clothes dryer, and a kitchen with a stove, oven, and refrigerator. And the cherry on top, the home allows guests to bring a maximum of two pets albeit with some conditions and additional fees.
Located in one of the most desirable neighborhoods in the area, the home is only 0.5 mi (0.8 km) from Lincoln Park Zoo, 1.5 mi (2.4 km) from John Hancock Center, 2 mi (3.2 km) from Chicago Riverwalk, and 2.3 mi (3.7 km) from Wrigley Field.
A home away from home! (No events allowed)Chicago, IL, US
5. Two-bedroom rental located at the heart of Old Town (from USD 363)
Convenience is the keyword for this two-bedroom rental. Located at the heart of Old Town, the home is close to several restaurants, bars, and shops as well as being 5 to 10 minutes away from downtown and the plethora of attractions there.
The rental itself features hardwood floors, a private deck, and a kitchen with granite & stainless steel appliances. Some amenities include two queen-sized beds, a double bed, fireplace, air conditioning, and TV.
¡¡Buena ubicación!! Oldtown / Lincolnpark cerca del centro y ElAccommodates: 6
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 14 days before check-in.
Top guest reviews
Amenities & Room:
amenities in the bathroom was a nice touch of high end productsthe beds were reasonably comfortablevery comfortable and accessible to everythingCleanliness:
very clean and exactly what we neededit was impeccably clean and the arrival and check in processes were very smoothit was fairly well stocked and very cleanHost:
check in and check out was super easy and the call into the property office was extremely helpfulRead more reviewsLocation:
great location very convenient nicely appointedthe location is great- close to old town’s shops and restaurants lincoln park and the lgreat location easy to get around townits easy walking distance to all lincoln park has to offer and then someyou get the benefits of the chicago sites/activities but escape the noise and bustle of a downtown/loop location
6. Three-level accommodation with sunroom (from USD 629)
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.
Casa espaciosa en el casco antiguo: a pie de vida nocturna y Mag Mile; Estacionamiento para 3 autosAccommodates: 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
7. Large house with a front yard and grill (from USD 529)
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!
Elegante casa de 4 dormitorios Old Town; Camina hasta la milla Mag, la vida nocturna y el parque Lincoln; EstacionamientoAccommodates: 20
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
8. 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
9. 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)
10. 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
11. 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
12. 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
13. 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
14. One-bedroom house with a front and back yard
This one-bedroom house offers both convenience and relaxation for its guests. Able to accommodate up to four people, the home features a queen-sized bed and a sofa bed. It has a back and front yard that invites guests to simply sit back, relax, and enjoy a nice drink. Inside, there is a fireplace, two flat-screen smart TVs, a travel crib, and a kitchen with basic appliances.
As for nearby locations, the home is only 0.4 mi (0.6 km) away from Lincoln Park Zoo, 1.2 mi (1.9 km) away from State Street, 2 mi (3.2 km) away from Chicago Riverwalk, 2.2 mi (3.5 km) away from Navy Pier, 9.2 mi (14.8 km) away from Chicago Museum of Science and Industry.
Airbnb Old Town Chicago.Chicago, IL, US
15. Warehouse-turned house on Chicago's newest neighborhood
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
16. A luxurious abode with baby gear
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
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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