Apartment vacation rentals in North Side

5 out of 5 average rating, 274 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.

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.

4.99 out of 5 average rating, 105 reviews

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, 111 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.

4.93 out of 5 average rating, 228 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.

Superhost

A modern living area features a gray sectional sofa paired with a mustard-yellow armchair. A sleek coffee table sits atop dark flooring, complemented by a decorative plant and contemporary lighting. A mounted TV and an electric fireplace add functional elements to the stylish decor.

4.84 out of 5 average rating, 242 reviews

★Bright & Bold 1BR in Roscoe Village + Fireplace★

At this swanky home, you'll love the bold finishes, in-suite laundry, and private fully-equipped kitchen. Located in “village within the city” known for its charming and laidback vibe, you're near a nice array of casual taverns, independent shops, and cute cafes. Kick back on the couch over a good Netflix show, sleep in on an ultra-comfortable memory foam bed, or create a spa-like experience in the bathroom with rainfall shower, favorite tunes on the Bluetooth speaker, and ultra-soft towels.

A bright hallway is illuminated by natural light, showcasing a mix of art and plants. Shelves with various glassware and plants line one wall, while framed artwork featuring mountains and landscapes adds character. Light wooden flooring runs throughout the space.

4.99 out of 5 average rating, 144 reviews

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Superhost

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, 368 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.

The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.

4.98 out of 5 average rating, 128 reviews

Belmont Pleasures - hot tub / arcade gaming room

Welcome home! If you’re looking for a unique experience to enjoy with your friends and family come have some fun in this beautiful luxury home, located in belmont-cragin neighborhood Chicago IL 60634 The spacious house includes 3 bedrooms, 4 full bunkbeds , 2 queen beds , 2 sofa queen beds , 2 & 1/2 bathrooms . Whether you’re looking to book for a birthday, bachelor/bachelorette gathering, or trip with family and friends, this place has something for everyone.

A spacious living area is framed by an archway, featuring warm wooden flooring and soft lighting. A yellow armchair adds a pop of color beside a minimalist lamp, while a dining table surrounded by chairs sits invitingly in the backdrop, complemented by potted plants.

4.95 out of 5 average rating, 704 reviews

Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

An open-concept living area is featured, showcasing a dark sofa complemented by light-colored pillows. A round coffee table sits on a patterned rug, and a dining area for four is visible nearby. Modern kitchen appliances are neatly arranged against the backdrop of sleek cabinetry, with natural light flowing through a large window.

4.97 out of 5 average rating, 102 reviews

Beautiful Remodel in Sought After Wrigleyville

Modern comfort meets unbeatable location in this freshly renovated 1BR/1BA Wrigleyville gem. Enjoy the "new unit" feel with fresh paint, new appliances, and soaring 10-ft ceilings. Nestled in Lakeview, you're steps from top restaurants, bars, theaters, and iconic attractions. Perfect for travelers seeking style, convenience, and a true Chicago experience. Public transit is a block away and Spothero parking behind the building.

A modern living area features a gray sofa facing a round marble coffee table. Behind, a built-in bookshelf holds various books. Natural light streams through multiple windows, illuminating a dining area with a round table and stylish chairs. Greenery adds a touch of nature.

4.95 out of 5 average rating, 129 reviews

Chic retreat near the best of Lakeview & Wrigley

Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!

A bright living room features hardwood flooring and a large, comfortable gray sectional sofa. Two unique yellow chairs are positioned nearby. A stylish TV unit and shelves display decor items, while light streams in through multiple windows, enhancing the open and inviting layout.