Vacation rentals in Andersonville, Chicago

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Top-rated vacation rentals in Andersonville, Chicago

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Guest favorite

Apartment in Edgewater

4.93 out of 5 average rating, 381 reviews

Ravenswood Guest House Annex

The Annex is a private apartment in an 100+ year old wood frame home just north of Andersonville. The Annex is a typical Chicago style 'in-law' garden apartment - located on the first floor of the house where we live - it is bright and clean and well appointed with comfortable furniture. (see pictures). It has large windows that look out on our garden and yard. Our daughter's family also lives on the property in rear coach house. There is easy access to Lake Shore Drive, Evanston and downtown.

Apr 22 – 29

$79 per night

Guest favorite

Guest suite in Lincoln Square

5.0 out of 5 average rating, 293 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 17 – 24

$122 per night

Guest favorite

Guest suite in Andersonville

4.96 out of 5 average rating, 319 reviews

Gorgeous, cozy 1-bedroom Suite in Andersonville

Our place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, location, complete privacy and NO cleaning fee. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.

Nov 25 – Dec 2

$78 per night

Guest favorite

Apartment in Andersonville

4.95 out of 5 average rating, 107 reviews

Jean's House—Restored Historic Andersonville Craftsman

Turn on the market lighting and sit in the garden with a glass of wine. Follow up with a Netflix show in the den. Start the next day in the breakfast nook, with windows on 3 sides and extra illumination from a Rejuvenation hand-made light. Take a short stroll to discover the many restaurants, cafes, and independent stores of Andersonville, known as the “Shop Local Capital of Chicago”. The unit is perfectly located in the heart of Andersonville and comfortably hosts 4 guests.

May 5 – 12

$164 per night

Guest favorite

Apartment in Andersonville

4.96 out of 5 average rating, 483 reviews

Stunning Retro Apartment in Andersonville

Stay in this perfectly situated apartment in the heart of vibrant Andersonville and find out why TimeOut Magazine calls this “The Coolest Neighborhood in the US”. Full of natural light, this 2 bedroom, 1 bath home has generous room sizes, and located on the ground floor of an immaculately kept vintage 4 unit building that has been fully upgraded with modern amenities. Plenty of free parking 24/7. Folks who stay here really will get an authentic Chicago-style experience.

Dec 2 – 9

$137 per night

Guest favorite

Apartment in Uptown

4.96 out of 5 average rating, 265 reviews

Cozy loft in Chicago's Uptown

Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; apartment on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. Andersonville (one of Chicago’s coolest neighborhood is a 15-minute stroll. CTA's Red Line/Wilson train station is 3 blocks away. Overnight street-parking decals also available for guests.

Oct 15 – 22

$101 per night

Guest favorite

Apartment in Andersonville

4.82 out of 5 average rating, 435 reviews

Lovely Andersonville Apt with Ideal Location

Large 1 bedroom with all the essentials and kitchen for your stay in Chicago's entertainment district. Steps away from all the amazing restaurants and shops in Andersonville, Uptown's Asia on Argyle (best Pho in the city!), and a number of music venues (Aragon, Riveria, and The Green Mill). You'll also be a short walk from Foster Beach and Chicago's Lakefront Trail, beautiful parks, and public transportation (CTA Red Line, Buses, and Metra train).

Jan 1 – 8

$75 per night

Superhost

Guest suite in Andersonville

4.85 out of 5 average rating, 317 reviews

Cozy and Private Andersonville Retro Studio

In the heart of Andersonville, this cozy, vintage-inspired studio apartment can be your home away from home. Located on the garden level, it is only 2 steps down to your own private oasis in the city. Separate private building entrance and no shared spaces in the entire basement suite. Sparkling clean and every detail considered for your comfort. Enjoy living like a local steps from Chicago's best 'hood, while experiencing the comforts of home.

Oct 1 – 8

$89 per night

Guest favorite

Apartment in Andersonville

4.98 out of 5 average rating, 166 reviews

Beautiful Hollywood-Ridge Suite in Edgewater

Beautiful, complete, and private apartment/suite in a historic Chicago Greystone located in the beautiful and diverse Edgewater neighborhood. Sleeps 1-4 persons (Queen bed in master bedroom and Deluxe Memory-Foam Queen Size Sofa Sleeper in living area). Suite features guest-controlled central air and heat, 2 flat screen TVs, private bath and shower, and full access to all rooms.

Feb 12 – 19

$125 per night

Guest favorite

Condo in Lincoln Square

4.98 out of 5 average rating, 329 reviews

Lincoln Square Gem!

Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. My partner and I live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!

Oct 14 – 21

$126 per night

Guest favorite

Apartment in Andersonville

4.92 out of 5 average rating, 396 reviews

Andersonville Living

Sunny 3 Bedroom 1 Bath located in Andersonville right off Clark St. with its shopping, bars and restaurants. The apartment has vintage charm with original woodwork and floors as well as modern amenities such as the new kitchen and central AC. There is a large sunny back deck for sipping your morning coffee, wifi, cable and Amazon for your media needs.

Oct 12 – 19

$132 per night

Guest favorite

Guesthouse in Andersonville

4.91 out of 5 average rating, 341 reviews

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 in the Midwestern aura of this apartment featuring robust wood floors and rustic-industrial decor.

Dec 6 – 13

$134 per night