
Waterfront holiday rentals in North Side
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in North Side
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

LakeHome Retreat- Hot Tub • Fire Pit • Bar & Games
Come enjoy our beautiful home it's the perfect place to relax, unwind & enjoy peaceful lake views. Whether you’re fishing, soaking in the hot tub or sipping coffee on the deck, it’s a quiet home away from home on a serene cul-de-sac. Enjoy stunning views of the lake while grilling or relaxing by the firepit on the beautifully landscaped patio & in the hot tub 🥂 🐶 Up to 2 furry babies are welcome & they’ll love the almost 1-acre fenced yard! 🌅 See weekly & monthly discounts for longer stays

The Lakefront Lookout (2BR)
Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, Navy Pier, Riverwalk, Soldier Field, The Field Museum, Oak Street Beach, and more. Additionally, guests are merely blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city!

3 Bed 3 Bath Lakefront Retreat, Parking Included
From the moment you step into the living room of my lakefront home, your breath will be taken away by the incredible scenery outside. Let the gentle sounds of the lake relax you and clear your mind during your tranquil stay. The interior is just as stunning with professionally designed decor, completely new appliances and thoughtfully curated amenities. You will have every modern comfort during your relaxing getaway and may not want to leave. Don't miss out on a true lakefront gem, book today!

Stone Mansion Sleeps 10-20 Free parking & TV
Giant, 4 bedroom, 2,300 square feet apartment on 2nd floor, near Red Line Train, bars, cafe's, shopping, restaurants, Lakefront and everything else Chicago has to offer. Large living room with bar area, TV and fridge for socializing before hitting the town. Dining room has a large table and 8 chairs. 4 bedrooms with 2 private rooms with king beds and one with a double bed. 4 futons for in the living room for extra sleeping space two (2) parking spots in the west facing garage on premises.

2BD/2BA MAG MILE MASTERPIECE (+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 - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

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

Studio flat in the heart of Chicago's Gold Coast
Come stay in our one-bedroom studio apartment with a fully equipped kitchen and bathroom. Take in the perks of our central location with easy access to the Gold Coast beach and public transportation. Gibsons and the Original Pancake House are also a stone’s throw away. The property is the perfect refuge after a long day in the Windy City or sunbathing on the beach. After working hard and playing hard, a comfy bed with high-quality linens ensures you’ll be rested and ready for the next day.

Spacious & Elegant N Side Apt Near Beach & Transit
This spacious 1-bedroom apartment, just 1 minute from Marion Majony Griffin Beach, offers comfort and convenience for solo travelers, couples, or small families. Enjoy a fully equipped kitchen, cozy pull-out couch, and a dedicated workspace perfect for remote work or studying. Free street parking is available, or take public transit just a block away to the Red Line for easy access to the city. With its prime location and thoughtful amenities, we warmly welcome all travelers to our listing.

Spacious & Stylish 2BR-2BA Apt Steps from The Bean
Enjoy this comfy, renovated and super spacious 2BR and 2BA apartment in the heart of Chicago's Loop with views of Lake Michigan. Surrounded by the most popular stores and restaurants, this unbeatable location is less than a one-minute walk to Michigan Ave, Millennium Park, State St. Shopping, The Chicago Theatre and Chicago’s landmark, ‘The Bean'. It is an ideal location to move around in public transportation, as all CTA lines and plenty of bus lines are just within two blocks!

Old Town/Lincoln Park Luxury Home Garage & Rooftop
Old town luxurious townhouse with rooftop, patio and attached garage (with Level 2 electric car charger for any type of electric car). The extra wide floor plan allows for 4 large bedrooms and 2.5 bathrooms spread over 4 levels of living. One block away from Brown Line station and 4 blocks away from Red Line station and best of Lincoln Park shopping. 10 minutes walk to North Avenue Beach or Lincoln Park Zoo. 5 minute walk to Second City, Zanies and Old Town dining & nightlife.

Spacious&Modern Condo | Near Dwtn | Secure Parking
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! ✨

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.
Popular amenities for waterfront rentals in North Side
Waterfront apartment rentals

Sheridan Beach Apartment

8BR Retreat for Groups w/ Easy City Access

The Wine Down

Cozy Chicago Apartment next to the River

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

Executive Apartment on Lake Michigan with parking

⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️

COZY unit near Michigan Lake 2nd floor/no elevator
Waterfront house rentals

Beautiful and secluded 3 bedroom ranch style home

Gold Coast Home|Rooftop |PoolTable |Parking |Views

Bike & Kayak: Lakefront Prospect Heights Home

CasaNova Modern City Living

Lakefront View Getaway Home! Hot tub! Kayak!

Lake Home-3 blocks to beach/harbor 10 min 2 Loop!

House 1 minute from O'hare Airport

Cozy 5-bedroom with lake views and spacious deck
Waterfront apartment rentals

Modern Wrigley Oasis with Parking!

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)

Iconic Style, Charming Lake View

Where you want to BE! Stylish, Comfy, Luxe

Best view and luxury style, Located in Downtown

River North Hideaway w/Amazing Views and Parking

Bronzeville Tribe Palace Loft

MAG MILE MEGA Entire Floor 4BD/4BA (+Roof/Gym)
Destinations to explore
- Chicago Holiday rentals
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- Apartment rentals North Side
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- Waterfront rentals Illinois
- Waterfront rentals United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- 875 North Michigan Avenue
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Washington Park Zoo
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606
- Things to do North Side
- Art and culture North Side
- Food and drink North Side
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- Sightseeing Illinois
- Sports activities Illinois
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