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Vacation rentals in Andersonville, Chicago

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Top-rated vacation rentals in Andersonville, Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guesthouse in Andersonville
Private, Charming, Coach House Loft in Andersonville
After a day exploring the city, cook dinner in an open-plan kitchen with dark hardwood surfaces. Gather around an enduring wood table and unwind within the Midwestern aura of this apartment featuring robust wood floors and rustic-industrial decor. This is a one of a kind space in the City of Chicago. We have meticulously renovated this space to be a comfortable and refined sanctuary for our guests. The touches blend an eclectic sense of Midwest farmhouse with a nod to the rustic & industrial from our city's vibrant past. Access to the loft is completely private and secure. Each guest receives a unique code to enter the space, so there are no keys to worry about. We live on the property, but the loft itself is detached from the home. So, we are available if you need anything, but also provide complete privacy for our guests. Andersonville has many restaurants, bars, unique retail shops, antique stores, book stores, and boutique grocery and liquor stores nearby. There is also nightlife, like Hopleaf, as well as Sun Wah BBQ and the best Pho in Chicago. We are located on a quiet street but only a block walk from buses on Clark Street to the West, Foster to the North, and Broadway to the East. We're a 7 minute walk to the Red Line train at Argyle, which will get you downtown in about 20 minutes, and in to the heart of the Loop within 25 minutes. Although there is no private parking on site, there is typically plenty of street parking, depending on the time of arrival. Around 4:00 PM (check in time) there will be no problem parking on our block. The streets around us aren't permitted either, so all parking on the surrounding residential blocks is free as well. Set in Andersonville, the apartment is steps away from the charming restaurants, cocktail bars, trendy boutiques, and cafes along North Clark Street. Foster Beach and Kathy Osterman Beach House are a short walk away.
$149 per night
Private room in Andersonville
Entire floor urban retreat private guest suite
Our private urban retreat with vaulted ceilings, features a private master bathroom and sitting room that takes up the entire floor. Located in Andersonville (2nd coolest neighborhood in the world according to Time Out), we are steps from the train, beaches, great dining and shopping. Walking distance to the Aragon Ballroom and Riviera Theater. Close to Wrigley Field and the Cubs. It's a quick train ride downtown or Evanston. We’re taking extra steps to clean and sanitize!
$82 per night
Condo in Andersonville
The Bright Retreat in Andersonville
Stay in the heart of Andersonville when you book this bright, newly renovated condo. The home is one block from Clark Street near some of Chicago's best restaurants. It is 3 blocks from the Argyle Red Line stop, which will get you to Wrigley in 15 minutes and downtown in 30 minutes. The home includes a fully-stocked kitchen, in unit washer & dryer, a free dedicated parking spot, queen-size bed and a couch with queen-size memory foam mattress.
$119 per night

Stay near Andersonville, Chicago's top sights

Photo of Lady Gregory's Irish Bar & Restaurant
Lady Gregory's Irish Bar & Restaurant93 locals recommend
Photo of Little Bad Wolf
Little Bad Wolf82 locals recommend
Photo of Calo Ristorante
Calo Ristorante54 locals recommend
Photo of Reza's Restaurant
Reza's Restaurant55 locals recommend
Photo of Fireside Restaurant & Lounge
Fireside Restaurant & Lounge20 locals recommend
Photo of m.henry
m.henry95 locals recommend

Other great vacation rentals in Andersonville, Chicago

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Inviting Stylish Home with Covered Patio
$108 per night
Guest suite in Andersonville
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Rental unit in Uptown
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Rental unit in Andersonville
Deluxe 1BR Apt steps away from Shops & Cafés
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Rental unit in Andersonville
Charming Chicago getaway with Classy finishes.
$97 per night
Rental unit in Uptown
Vibrant studio close to Andersonville and train
$62 per night
Rental unit in Edgewater
Edgewater Minimalist Studio Apt
$59 per night
Rental unit in Andersonville
Edgewater, private, charming coach house 2 (of 2) Licensed by the City of Chicago 2209376
$115 per night
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