Holiday rentals with lake access in North Side

A bright dining space features a round table surrounded by wooden chairs, complemented by natural light from large windows. A decorative rug lies beneath the table, and a vintage wooden display cabinet occupies one wall, showcasing various items. A plant is seen near the window.

4.9 out of 5 average rating, 218 reviews

Spacious Vintage 3 BR in Chicago's NorthCenter!

Location, location, location! Vintage 3BR second floor Apartment only 10 Blocks from Wrigley Field & 2 miles from Lake Michigan. Bus stop in front, CTA Brownline train to loop a 5 minute walk, bus/CTA from OHare airport 1 block away. Washing machine and dryer in apartment. Neighborhood setting. Walk to restaurants, local breweries, Old Town School of Folk Music & theaters, ballgames, concerts, Trader Joe's, banks, boutiques . Divy bikes, CVS & Starbucks across the street. Garage option.

A modern chef's kitchen is shown, featuring an island with seating for four. Sleek dark cabinetry contrasts with light countertops and stainless steel appliances. A bowl of fruit adds a touch of color, while glass pendant lights provide illumination above the island.

4.96 out of 5 average rating, 135 reviews

Modern MAG Mile 2BD/2BA (+Parking/Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Parking spot on-site in/out access!! - Tranquil rooftop overlooks Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows

A spacious living room features large windows that fill the area with natural light. A coffee table sits at the center, surrounded by stylish seating, including a sofa and armchairs. Artwork adorns the walls, enhancing the modern decor.

5 out of 5 average rating, 148 reviews

Remodeled, Near Loyola, Beach and Subway

Stylish and sophisticated, this remodeled 3 bedroom, 2 bath private apartment is in a prime location, 3 blocks from Hartigan Beach, and 2 blocks to the Loyola Red Line "L" station to take you to Wrigley Field, downtown & many locations in between. We are 2 blocks from Loyola University & about 4 miles to Northwestern University. Located on a quiet, residential tree-lined street, we are a 2 block walk from all manner of restaurants & conveniences associated with our proximity to Loyola.

A modern kitchen features sleek gray cabinetry and stainless steel appliances, including a refrigerator and oven. A neutral area rug complements the wood flooring. Natural light is provided by large windows, and stylish wall decor adds a contemporary touch to the space.

4.99 out of 5 average rating, 210 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

A modern living room features a light gray sofa paired with dark accent pillows. Natural light fills the space through large windows, complemented by dark curtains. A stylish armchair and a side table sit next to the sofa, while a flat-screen TV is mounted on the wall.

4.98 out of 5 average rating, 130 reviews

Free Parking| King Bed |Private Balcony |Sleeps 8

Your stylish city escape—unwind, explore, and experience Chicago like never before. Our modern, spacious condo is perfect for families, groups, and business travelers looking for a comfortable, stylish, and well-located stay. Whether you're in town for a concert, conference, sightseeing, or a weekend getaway, you'll find everything you need for a relaxing stay. ONE SECURE INDOOR PARKING SPOT IS INCLUDED❗❗❗ ✨ Book your stay today & experience Chicago in comfort and style! ✨

A light-filled living room showcases soft gray walls and hardwood flooring. A comfortable sofa and armchair are positioned around a decorative area rug. A television is mounted on a console, while a lamp beside a side table adds warmth to the space.

4.99 out of 5 average rating, 294 reviews

Cozy 3BR on Chicago's North Side & Free Parking

Enjoy this charming 3-bedroom condo with free on-site parking just three blocks from Lake Michigan. Convenient access to public transit, including the express bus to downtown (9 miles), Navy Pier, and Grant Park. The CTA Jarvis station is only three blocks away. Perfect for families, business travelers, and couples, this condo is also close to Loyola (1.5 miles) and Northwestern universities (2.5 miles). A great home base to explore all that Chicago has to offer!

A well-lit living area features a striped sofa accompanied by two modern armchairs. A wooden coffee table sits in the center, complemented by a patterned rug. Shelves display an array of silverware and decorative items, adding character and visual interest to the space.

4.93 out of 5 average rating, 266 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This cozy AirBnb is perfectly situated. A beautifully clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation & restaurants, red line "El" trains & bus routes. Apt has private, queen bedroom, en suite full bathroom, living room w/queen sofa bed, TV, dining table, & partial kitchenette. NOTE: No full kitchen.

A spacious living area is furnished with a light-colored sofa, two armchairs, and an entertainment unit containing books. Soft lighting from a lamp creates a warm atmosphere. A geometric area rug adds visual interest to the carpeted floor. The sloped ceiling enhances the cozy feel of the space.

4.97 out of 5 average rating, 306 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.

4.95 out of 5 average rating, 141 reviews

A cozy living room features a warm fireplace with a flat-screen TV mounted above. Comfortable leather chairs and a plush sofa surround a coffee table, while large windows allow natural light to fill the space. Potted plants add a touch of greenery.

Bungalow in Chicago

Chicago Bootlegger House Sleeps 10-20

Walk to restaurants, groceries, shopping, Wrigley Field, Lake Michigan, Beaches, Boat Harbor, Lincoln Park Zoo, night life, bars, clubs, Red Line Train, Lakeshore Drive and more; all just a few blocks from your door. Giant house on 2 levels with over 3,500 square feet of living space and 6 bedrooms. Nicely decorated and lots of places to sit and mingle or watch one of the 85" TVs. Private 2 spot parking in garage and a parking pad for oversized vehicles.

A spacious living area is presented, featuring a large gray sectional sofa. Natural light enters through expansive windows, illuminating the room. A fireplace and a mounted television are visible on the wall, with plants enhancing the decor around the space.

4.98 out of 5 average rating, 312 reviews

Near Lake Michigan & Wrigley Field

Available 2B/2B condo with 2 King Size Beds. One block from the Aragon Ballroom and Riviera with great views of Uptown and two blocks from Lake Michigan. It’s also a perfect place to stay if your in town for a Cubs game. You can see the stadium from the rooftop deck. Walking distance to everything you need, 2 train stations, groceries, gym, restaurants/ bars. The perfect place to come and go as you please with easy key code entry.

4.98 out of 5 average rating, 144 reviews

The living room features warm pine walls, offering a cozy atmosphere. A dark, spacious sofa is positioned alongside a wooden coffee table. Two lamps illuminate the space, framed artwork adorns the walls, and potted plants are placed on the windowsill, adding a touch of greenery.

Guest suite in Chicago

Cozy Andersonville Cabin

Our cabin-in-the-city is a relaxing garden apartment, located in the popular LGBTQ+ friendly Andersonville area of Chicago. The cabin unit is decorated in bear and nature themes, with warm and cozy pine walls - like you were renting a cabin in the woods! Our place is a half a block from the main strip. Plenty of great shopping, award winning dining, and fun night life is just steps from our house!

A cozy bedroom is depicted with a spacious bed featuring white linens. On either side, elegant lamps provide soft lighting. A colorful artwork adorns the wall above the bed, and framed art pieces are visible on the nearby walls, contributing to the room's inviting feel.