Old Town, Chicago vacation rentals

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Top-rated vacation rentals in Old Town, Chicago

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Guest favorite

Townhouse in Lincoln Park

4.98 out of 5 average rating, 229 reviews

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit

The newly renovated spacious apartment is furnished with brand new modern king bed in the bedroom to ensure restful nights. In large living room, beautiful cherry dining table to enjoy morning coffee and comfortable L-shape leather sofa for watching your favorite movies from Netflix on 43" flat screen TV. The brand new fully equipped kitchen has a granite countertops, stainless steel appliances. The modern marble bathroom has a huge mirror over the sink, glass sliding shower doors, a full size bath tub and a hair dryer. Spacious 3 room apartment with all the amenities specified above is for guests use only and free residential parking permits provided upon request. I'm always available. I live on the 2nd floor of the townhouse with my husband and work at a bridal boutique which I own on west Armitage Ave. The apartment is super conveniently located in the Armitage/Sheffield. It's 2 1/2 blocks or 5 minutes walk to both Brown and Red line stations which make getting around Chicago fast and easy. Visiting lake front Millennium Park takes less than 20 minutes from the apartment. My neighborhood is surrounded by Old Town, full of local shops and restaurants, Wrigley Field, eclectic Bucktown shops, and the Lincoln Park Zoo. The 3 Michelin-starred restaurant, Alinea is 2-minute walk from the door. Take either Red ( North/Clybourn ) or Brown (Armitage/Sheffield ) line for exploring Rush st( 1 stop) Water Tower, Michigan Ave, Mag miles, Gold Coast( 2 stops ) The Navy Pier( 3 stops) Millennium Park, Cloud Gate/ The Bean, Buckingham Fountain, Art Institute of Chicago,( 4stops). Both stations are within 5 min walking distance from the apartment. It's also a short cab or Uber ride to Michigan Ave. Gold Coast. No smoking, no street shoes, no parties allowed. The nightly rates are for 2 guests only and $25 guest fee applys for 3rd guest. There is a $500.00 penalty for breaking the each rule.

Nov 18 – 25

G$43,470 GYD per night

Guest favorite

Apartment in Lincoln Park

4.98 out of 5 average rating, 298 reviews

Redesigned Lower Level Studio in Historic Building

The space is very comfortable, quiet and cozy. There are new cabinets, granite counter tops, all new appliances and a washer and dryer. Guests sleep on a king size tempur-pedic mattress or a queen size trundle style pull out sofa. There is hi-speed wi-fi, cable TV (Showtime), 55' flat screen TV and a wood burning fireplace. The bathroom is immaculate and includes a full bathtub with shower. This is a private apartment and you will have access to the entire suite. There is a back and front door with adequate lighting and easy access for guests. My family and I live next door and I will be available at our guests convenience. I am happy to provide any information, recommendations, directions etc.. I am easy to reach and am always available but will not intrude on our guests privacy. This unit is on a beautiful tree lined street in the heart of Old Town, close to St. Michael's Church, Steppenwolf Theater, and the Second City Improv Theater. The location allows for easy access to all of Chicago by either train, bus, or car. The blue and brown line train stations are within walking distance. Street parking is readily available and no permits are necessary. A Chicago Cab or Uber can get you to Milleniumm Park in approx. 15 minutes. Four adults can comfortably stay in this unit. The king size tempur_pedic mattress is the pinnacle of comfort and the queen size trundle style pull out sofa is comparable to sleeping on an actual queen size mattress. The queen size bed could comfortably fit 3 children. There is street parking readily available but I can provide an assigned space behind the building if necessary, for additional cost.

Oct 24 – 31

G$25,878 GYD per night

Guest favorite

Apartment in Lincoln Park

4.99 out of 5 average rating, 196 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Apr 3 – 10

G$39,448 GYD per night

Guest favorite

Apartment in Lincoln Park

4.89 out of 5 average rating, 144 reviews

Lincoln Paradise– Steps to Park & Zoo!

This semi-basement apartment is located on a tree lined street full of gorgeous, historic buildings. With easy access to shopping, dining and drinking via Wells St & North Avenue- you'll love this location! Walking distance from Lincoln Park, the Lakefront, North Ave Beach, and the Lincoln Park Zoo. Feel right at home with the bright and welcoming layout, with every convenience of home provided. This garden unit is spacious, you'll have plenty of room to relax during your stay in the Windy City!

Nov 22 – 29

G$49,541 GYD per night

Guest favorite

Guest suite in Lincoln Square

5.0 out of 5 average rating, 297 reviews

Private Lincoln Square one bed+bath studio apt.

Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

Sep 18 – 25

G$29,244 GYD per night

Guest favorite

Apartment in Lincoln Park

4.96 out of 5 average rating, 379 reviews

Sophisticated Flat in Historic Building

Nestled in the charming Old Town Triangle of Chicago, this luxurious flat offers a seamless blend of historic charm and contemporary sophistication. With its soaring ceilings and elegant arched windows, this immaculate space boasts a truly captivating ambiance. Impeccably designed interiors ensure a truly indulgent stay, while the building's rich heritage adds an unforgettable sense of place. Treat yourself to the ultimate Chicago getaway and bask in the allure of this stunning residence.

Oct 19 – 26

G$64,995 GYD per night

Guest favorite

Loft in Lake View

4.96 out of 5 average rating, 422 reviews

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

Nov 10 – 17

G$31,673 GYD per night

Guest favorite

Condo in Lincoln Park

4.92 out of 5 average rating, 248 reviews

Old Town Pied-à-Terre w/Pvt Terrace and Parking

Our bright modern 2 bedroom condo has 13 ft ceilings and an amazing private terrace. It's in the heart of Old Town, right on Wells St - steps outside the door are some of the city's best restaurants, cafes, and bars. Just a 5 minute walk to two world-renowned comedy clubs: Second City and Zanies. The Chicago History Museum, Lincoln Park Zoo, and the lake are a quick walk too. The Sedgwick CTA stop is nearby too! Please note: patio cushions are available May through October.

Apr 4 – 11

G$87,556 GYD per night

Superhost

Apartment in Lincoln Park

4.79 out of 5 average rating, 173 reviews

Perfect 1br In Lincoln Park - Steps to Depaul!

This charming garden unit in Lincoln Park is ideally situated for any type of traveler! There are plenty of parks, dining, nightlife, and shops nearby. The main DePaul campus is just a quick walk away as well, perfect for families coming to visit their students or tour the school! You can easily take the 'El' train downtown to see all of Chicago's iconic sights. After a long day out and about in the city, come back to this cozy gem on a quiet, tree-lined street and unwind.

Jan 17 – 24

G$30,073 GYD per night

Guest favorite

Apartment in Lincoln Park

4.83 out of 5 average rating, 211 reviews

Cozy Lincoln Park Studio - Steps to Zoo!

This cozy studio in the heart of Lincoln Park is just steps away from some of the best experiences that Chicago has to offer! Just a block from the Lincoln Park Zoo and near the great restaurants and bars of the neighborhood, there's something here for everyone. See a show at the world-famous Second City, take a quick ride up Clark St to see the Cubs play at historic Wrigley Field, or just stay in and relax, there's no wrong way to spend your time in the Windy City!

Jan 30 – Feb 6

G$20,063 GYD per night

Guest favorite

Apartment in Gold Coast

4.89 out of 5 average rating, 140 reviews

Charming Gold Coast One-Bedroom Near Downtown!

Perfect Gold Coast studio near downtown, the lake and everything else! We are nestled in the Gold Coast in an excellent location. Public Transportation, restaurants, shops, museums and grocery stores are all steps away! The apartment is within an art deco style mid rise and has everything you need to be your home away from home while you're visiting the city of broad shoulders. Chicago Shared Housing Registration Number: R21000073420

Jan 9 – 16

G$21,118 GYD per night

Guest favorite

Apartment in Lincoln Park

4.87 out of 5 average rating, 273 reviews

Historic Old Town Flat - Minutes from Downtown!

Built in 1886, our "Boland House" offers guests a rare chance to stay in an architecturally significant residence on a beautiful tree-lined street in Historic Old Town district! The original owner was chief of plasterwork projects for the "White City's" 1893 World's Columbian Exposition - combined with modern day conveniences. If you've always wanted to stay in an authentic Chicago Victorian brownstone, you've found it!

Mar 6 – 13

G$38,438 GYD per night