Vacation rentals in Near North Side

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Top-rated vacation rentals in Near North Side

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Top guest favorite

Apartment in Lincoln Park

5 out of 5 average rating, 281 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.

Guest favorite

Private room in Lake View

4.95 out of 5 average rating, 115 reviews

Fantastic Location / Private Room

Enjoy easy access to everything from this perfectly located home base. Walking distance to Wrigley Field, The Vic, The Briar Street Theater (Blue Man Group), some of the cities best restaurants, bars and coffee shops, Advocate Illinois Masonic Medical Center, The CTA’s Red Line which takes you right downtown to the Loop, Depaul, Chinatown and a host full of other Chicago destinations. There’s really no need for a taxi or Uber with so much that is walkable or accessible from the red line.

Top guest favorite

Apartment in Magnificent Mile

4.97 out of 5 average rating, 76 reviews

Gold Coast Pristine 3BD|2BR| Patio |Parking| Beach

FREE GARAGE PARKING! Garage Clearance 6ft. Step into luxury in this modern loft with 3 bedrooms, 2 bathrooms and a private patio with breathtaking views. Experience the feeling of being at home in a bright and spacious haven amidst Chicago's most sought-after neighborhood "Gold Coast" This centrally located gem is situated within walking distance of much of Chicago Downtown's exquisite dining, upscale boutiques, popular tourist destinations, and just a stone throw away from Oak Beach.

Guest favorite

Apartment in River North

4.93 out of 5 average rating, 87 reviews

Luxury Loft Collection 01 - Terrace - River North

BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious building in bustling River North-the city's center of main nightlife and restaurants. This ultra high-end apartment features a private elevator, private terrace, free secured parking, 24 hour doorman, 3 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

Superhost

Apartment in Near North Side

4.82 out of 5 average rating, 796 reviews

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Superhost

Private room in Little Italy

4.82 out of 5 average rating, 205 reviews

ChicagoRiver Double Room

Nicely decorated Private (10x11 sq ft) Room w/designated work station, well-lit, *shared common bathroom* (other guests may be in the premises). This is NOT a full condo rental; just 1 room. Quiet & clean, 2 miles from downtown, walking distance to dozens of restaurants in Taylor Street & Little Italy. Perfect location in a quiet neighborhood, but still close to the city to enjoy food& music festivals, free concerts in Grand Park, Museums, Broadway shows, etc

Superhost

Apartment in West Town

5 out of 5 average rating, 3 reviews

Downtown Chicago Retreat 2BD/2BA Views+Gym+Rooftop

Experience downtown Chicago living at its finest in this stunning 2-bedroom apartment, Sleek black and gold accents, in the heart of the River West. Wake up to breathtaking city views and step out to world-class attractions just minutes from your door. Enjoy a gourmet kitchen with high-end appliances, stylish baths, in-unit laundry, gigabit Wi-Fi, and free parking. Building amenities include a rooftop lounge and gym—perfect for business or leisure.

Apartment in Streeterville

4.71 out of 5 average rating, 351 reviews

Sonder Onterie | King Studio Apartment

Welcome to Onterie, where modern style meets an unbeatable location in the heart of Chicago's Magnificent Mile. You'll have world-class shopping and award-winning dining at your fingertips. Each apartment includes a fully equipped kitchen, in-suite laundry, and a Roku to stream your favorite shows. Unwind in the outdoor courtyard, or find focus in our co-working space. Onterie offers the perfect blend of city and lakeside living.

Top guest favorite

Apartment in Magnificent Mile

4.99 out of 5 average rating, 106 reviews

Chic 2BR Gem with Fireplace

Discover urban luxury in our 2BR, 2BA Gold Coast haven. This stylish apartment boasts a warm fireplace, sleek granite countertops, and a cozy layout. Immerse yourself in city living at its finest, right in the heart of Chicago's prestigious Gold Coast neighborhood. Perfect for both business and leisure travelers, our space combines modern comfort with the vibrant energy of one of the city's most coveted neighborhoods.

Top guest favorite

Condo in West Town

4.97 out of 5 average rating, 828 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Superhost

Hotel room in The Loop

4.79 out of 5 average rating, 376 reviews

Selected by hotel

- A spiffy new Essex in place of the traditional old Essex – it’s a breath of fresh fabulousness. Enviable location across from Grant Park. - Stylish rooms treat you to espresso machines, handheld steamers, Frette robes, and smart TV with streaming capabilities - Overindulged while out on the town? Sweat it out in the onsite gym offering Peloton bikes.

Guest favorite

Condo in Lincoln Park

4.9 out of 5 average rating, 307 reviews

Old Town Modern | Private Terrace + Parking

Thoughtfully designed Chicago Old Town condo with rare 160 sq ft private terrace and underground parking. This stunning 2BR/2BA features soaring 13-foot ceilings, spa bathroom with Jacuzzi, and premium amenities. Walk to Lincoln Park Zoo, North Avenue Beach, world-class dining, and Second City comedy. Superhost with 290+ five-star reviews.