Apartment vacation rentals in Ravenswood

4.99 out of 5 average rating, 110 reviews

A bright living room features large windows allowing natural light to fill the space. Comfortable seating includes a spacious couch and decorative poufs. A smart TV is mounted on the wall, and plants bring a touch of greenery, enhancing the relaxing environment.

Apartment in Avondale

Plants and Art | Near Trendy Restaurants & Bars

Light-Filled Apartment Near Chicago’s Best Restaurants & Bars • Friends & Couples • A/C • Coffee Station w/Local Beans • Fully-Equipped Kitchen Whether you’re in town to explore or unwind, you’ll love the proximity to restaurants, cafes, and live music venues - the perfect home base for your Chicago adventure. Extra Fees: *only available upon request and approval* Early Check In@ 2pm : $50 @10am:$100 Late Checkout@ 1pm: $50 @9pm:$100 Shipping: $25 + UPS fees Required for 7+ Days: $80 Cleanin

A cozy living room features a dark blue sofa with decorative pillows, a light brown leather armchair, and a glass coffee table atop a patterned area rug. Two large windows allow natural light to illuminate the space, which is adorned with a gallery of framed artwork on the walls.

4.97 out of 5 average rating, 112 reviews

Brand new 2 bed 2 bath apartment in Lincoln Square

Nestled on a quiet tree-lined street, this brand new home is 3 houses from the Chicago River. A quick walk to Lincoln Square, a locals-only destination for brunch, shopping, craft beer, and fantastic food. Relax in the secluded primary suite with a massive zero-threshold shower or walk to the nearby grocery stores to cook a gourmet meal in the fully equipped kitchen. Offering plentiful free parking in a central location, plus a short walk to the Brown Line CTA train to anywhere in the city.

A well-lit studio apartment features a spacious bed and a comfortable seating area with a sofa and coffee table. Natural light fills the room through multiple windows, and a collection of decorative pillows adds a splash of color. A wooden dresser and striped rug enhance the interior.

4.94 out of 5 average rating, 231 reviews

Spacious, light-drenched studio-private entrance!

Sun-filled private apartment in Lincoln Square! Spacious & well-appointed studio apartment features newly renovated kitchen and 1.5 baths (spa shower!) Located in the Lincoln Square neighborhood, you’ll be steps to restaurants, cafes, pubs & shopping. Close to CTA Brown Line (Rockwell) stop, as well as Western, Foster & Lawrence buses. Just 3.4 miles to Wrigley Field. One block to Swedish Covenant Hospital. Short bus/ride-share to Andersonville, Chicago Lakefront & Foster Beach! Kid friendly.

Apartment in Andersonville

A spacious living room is featured, with a large blue sofa adorned with pink cushions. Two cozy armchairs with blue upholstery flank a glass coffee table, which is positioned on a decorative area rug. A television stands against the wall, while soft lighting illuminates the space.

4.98 out of 5 average rating, 260 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.

4.93 out of 5 average rating, 220 reviews

A well-maintained garden unit is framed by a neatly arranged wooden fence. A covered porch with wooden railings offers a welcoming entryway. Snow blankets the small garden at the front, and the surrounding buildings display a mix of brick and stone facades.

Apartment in Lake View

Charming Apt. near Wrigley/Cubs, Ravenswood/Uptown

Welcome to our family-friendly & cozy 1-bedroom/1 bathroom apartment! We are walking distance from Wrigley Field, Montrose Beach, Andersonville restaurants, Green Mill Jazz Club, Riviera, Lincoln Square, Target and grocery. Close to Red, Purple & Brown CTA trains and 22, 78 bus lines to reach airports & top sights. Street parking is open & free (check signage!) We are a smoke-free home directly across from a school with playground in a very quiet & safe neighborhood: Ravenswood/Uptown.

4.99 out of 5 average rating, 300 reviews

A bright bedroom features a spacious bed dressed in white linens, surrounded by vibrant, tropical-inspired wallpaper. Two windows allow natural light to fill the room, accented by subtle shades and animal motifs. A small red chair is positioned near the bed, adding a playful touch.

Apartment in Lake View

A Whimsical Fairy-tale Loft in Ravenswood Chicago

Welcome to Bluebird Inn, an intimate, thoughtfully designed urban inn that will serve as an oasis as you embark on your exploration of Chicago. Nestled above the Long Room, a beloved neighborhood tavern and coffee house (Bad Johnny's, Nice Guy Food Co., Cash's Kitchen and AJ's Bakery & Diner), you can start your day downstairs with breakfast and coffee and stop in for a nitecap before heading up to retire for the evening. Settle in & enjoy the amenities and approachable luxury.

4.97 out of 5 average rating, 411 reviews

A cozy living area displays a green sofa facing a TV cabinet with a flat-screen television. A round table is positioned in the center, surrounded by two ottomans. Light streams through the window, illuminating the patterned rug and creating an inviting space.

Apartment in Lake View

Charming, Spacious 3BR Lakeview Apt Near Transit

This newly remodeled 3-bedroom unit with 1-bath apartment is perfect for both leisure & business travelers. Located on a safe, tree-lined street, in the Lakeview neighborhood, with a completely private entrance of it's own. We are just a 5 minute walk away from the CTA Irving Park Brown Line, which will get you downtown in less than 20min. We are also conveniently close to Wrigley Field, Lake Michigan, Bus Stops, and other great neighborhood shops, restaurants, and nightlife.

Apartment in Andersonville

A spacious living area showcases a large sectional sofa and two turquoise accent chairs. A neutral coffee table sits at the center, while a vibrant wall artwork adds color. Natural light filters through the window, highlighting the warm wooden floors and modern decor.

4.95 out of 5 average rating, 569 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.

A light-filled living area features large windows with green curtains and a view of the courtyard. A comfortable sofa with decorative cushions is positioned next to a wooden coffee table, which holds a book and a small plant. A TV is set on a stylish console.

4.86 out of 5 average rating, 371 reviews

Renovated Designer Flat in Heart of Lincoln Square

Kick back with a fresh coffee and enjoy the designer touches of this renovated apartment, including marble worktops, wood floors and 1920s exposed brickwork. There are great courtyard views, while the memory foam mattress and super-sized sofa add real comfort. Lincoln Square is a quaint, family-friendly neighborhood. There's abundant German influence here, and great shops, restaurants, and bars line Lincoln Avenue. Downtown is 20 mins by train. Wrigley Field is close too.

A two-flat brick building is set in a green and landscaped area, featuring large windows that allow natural light inside. A set of stairs leads up to the main entrance, which is flanked by plants and outdoor greenery.

4.93 out of 5 average rating, 128 reviews

Beautiful, sunny 2nd floor 3BR/1BA w free parking

Sunny second floor 3Br/1Ba apartment in the tree-lined, walkable neighborhood of Lincoln Square. Updated apartment with original woodwork offers easy access to Wrigley Field (7 el stops), Lake Michigan beaches, and downtown Chicago. Free parking space included, close to Western brown line el station and Lincoln Square's many restaurants and shops. Old Town School of Folk Music is a 5-minute walk. 2 miles to beaches.

A bright living area is presented with a patterned armchair and a cozy sofa adorned with a colorful throw. A wooden coffee table is positioned in front, while a window with sheer curtains frames the view of the outdoor porch area.

4.95 out of 5 average rating, 399 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.