Holiday houses in Andersonville, Chicago

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Top-rated holiday rentals in Andersonville, Chicago

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Guest favourite

Apartment in Edgewater

4.93 out of 5 average rating, 382 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.

6–13 Mar

$199 NZD per night

Guest favourite

Guest suite in Lincoln Square

5.0 out of 5 average rating, 296 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

2–9 Oct

$306 NZD per night

Guest favourite

Guest suite in Andersonville

4.96 out of 5 average rating, 320 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.

28 Dec – 4 Jan

$181 NZD per night

Guest favourite

Apartment in Andersonville

4.98 out of 5 average rating, 189 reviews

Foster Flat - Retreat to your Home Away from Home

The perfect place to stay for your next trip to Chicago. This fully furnished 2 bedroom/1 bath unit features bright living spaces with modern decor. Located just a few blocks from the heart of Andersonville, you'll find coffee shops, restaurants, shopping and nightlife. Lincoln Square and Ravenswood neighborhoods are also nearby for you to explore. Conveniently located to public transportation (buses, Red and Brown Line trains, as well as Metra), you'll have no trouble getting around town.

24–31 Jul

$332 NZD per night

Guest favourite

Apartment in Edgewater

4.99 out of 5 average rating, 104 reviews

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a bus stop right around the corner and less than 10 miles from the heart of the city, your urban adventure awaits!

7–14 Dec

$320 NZD per night

Guest favourite

Guest suite in Lincoln Square

4.95 out of 5 average rating, 242 reviews

Great location, private entry and patio!

Large 1 bedroom space tastefully decorated and well equipped. Sleeps 4 (5 with available inflatable). Queen bed in BR, full size futon in LR. Spacious enough for 2 to work comfortably. Use of the patio, fire pit and grill. Located in vibrant Lincoln Square. Steps to the Rockwell brown line el station, restaurants, a bagel shop, and yoga/massage studio. A few blocks away are shops, restaurants and a movie theater! Easy street parking with free permits. Ask about winter specials!

24–31 Oct

$255 NZD per night

Guest favourite

Apartment in Uptown

4.96 out of 5 average rating, 267 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.

16–23 Oct

$230 NZD per night

Superhost

Apartment in Andersonville

4.82 out of 5 average rating, 437 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).

27 Dec – 3 Jan

$190 NZD per night

Superhost

Guest suite in Andersonville

4.86 out of 5 average rating, 319 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.

8–15 Oct

$278 NZD per night

Guest favourite

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.

26 Feb – 5 Mar

$306 NZD per night

Guest favourite

Condo in Lincoln Square

4.97 out of 5 average rating, 330 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!

28 Sep – 5 Oct

$315 NZD per night

Guest favourite

Apartment in Andersonville

4.92 out of 5 average rating, 397 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.

22–29 Sep

$330 NZD per night