Vacation rentals with lake access in North Side

4.89 out of 5 average rating, 203 reviews

The Bright Retreat in Andersonville

Stay in the heart of Andersonville when you book this bright, newly renovated condo. The home is one block from Clark Street near some of Chicago's best restaurants. It is 3 blocks from the Argyle Red Line stop, which will get you to Wrigley in 15 minutes and downtown in 30 minutes. The home includes a fully stocked kitchen, free parking spot (small and medium size cars and SUVs only, not large vehicles), in unit washer & dryer, queen-size bed, and couch with queen-size memory foam mattress.

4.98 out of 5 average rating, 108 reviews

The Ramblers Inn, Northside NEW Reno w/parking!

Our family 2-flat has been completely gutted to the studs renovated with new everything! This top floor 3 bed 1 bath home has CENTRAL A/C, in unit washer/dryer, and free parking on-site. This prime location is a short walk to Loyola University, beaches/playgrounds, public transportation and award-winning restaurants. Lake shore trail is less than a mile away. We are steps away from a large local grocery store. Your urban stay will feel like a relaxing retreat because of these conveniences.

5 out of 5 average rating, 132 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.

4.99 out of 5 average rating, 174 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

4.97 out of 5 average rating, 497 reviews

Apartment in Evanston

Charming, Sunny Apartment with Backyard Garden

House of the Blue Doors Enjoy staying with us in this spacious 1st floor flat. Furnished by the resident designer in tasteful neutrals, original curated artwork, one of a kind furniture and accent pieces. Sip morning coffee or a glass of wine in the sunlit kitchen or front porch, fire up the backyard grill for a barbecue. Soak in the award winning Chicago ceramic artist designed and made floor in the bathroom. Close to Northwestern, Chicago, Lake Michigan, everything Evanston offers.

Guest favorite

4.92 out of 5 average rating, 239 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.

4.97 out of 5 average rating, 297 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.

4.98 out of 5 average rating, 281 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, 274 reviews

Townhouse in Chicago

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit

This generously sized, quiet apartment, located in the highly sought-after Lincoln Park neighborhood, offers convenient access to acclaimed restaurants and boutiques, all within a five-minute walk. Its private entrance and proximity—less than four blocks—to both the Red and Brown Line "L" stations ensure effortless access to Chicago's attractions, most within a two- to five-stop train ride. Zoned parking permits are provided.

Superhost

4.9 out of 5 average rating, 175 reviews

Executive Apartment on Lake Michigan with parking

Stay in a furnished 2nd-floor apartment in a walk-in building with its own beach on Lake Michigan. Watch the waves from your living room or sit out on the terrace. -Free Wifi, -Onsite Parking with EV charging station -Steps away from parks, minutes away from universities, shopping, and restaurants -Less than 25 min drive to Wrigley Field, Downtown Chicago, Soldier Field, and museums.

4.99 out of 5 average rating, 636 reviews

Urban Comfort in the Heart of Chicago

This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and a newly remodeled en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.