Holiday rentals in Near North Side

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Top-rated holiday rentals in Near North Side

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Top guest favourite

Flat in Lincoln Park

5 out of 5 average rating, 277 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 favourite

Flat in Lincoln Park

4.88 out of 5 average rating, 233 reviews

Lincoln Paradise– Steps to Park & Zoo!

This semi-basement apartment is located on a tree lined street full of gorgeous, historic buildings. With easy access to shopping, dining and drinking via Wells St & North Avenue- you'll love this location! Walking distance from Lincoln Park, the Lakefront, North Ave Beach, and the Lincoln Park Zoo. Feel right at home with the bright and welcoming layout, with every convenience of home provided. This garden unit is spacious, you'll have plenty of room to relax during your stay in the Windy City!

Guest favourite

Serviced apartment in Lincoln Park

4.96 out of 5 average rating, 118 reviews

English garden apt. in the heart of Lincoln Park

Welcome to this new, totally furnished apartment in the heart of East Lincoln Park…only a 3 minute walk to the Lincoln Park Zoo! Apartment has been completely renovated with high finishes throughout. Living room boasts a 50” television with Dish TV, internet and a queen sleeper sofa! Gourmet kitchen with granite counter tops with an eat-in bar height counter top. Truly gourmet kitchen! Bedroom with en-suite European styled bathroom. Wall mounted television in the bedroom. In unit laundry.

Superhost

Townhouse in Magnificent Mile

4.83 out of 5 average rating, 214 reviews

Historic luxury townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after locations in the city! Located on one of Chicago’s famous streets, you’ll be a 5-minute walk from the historic Gold Coast beach and intimate views of Lake Michigan. The property is also within walking distance of the subway, where you can connect to the L trains, and the Magnificent Mile. It is the perfect place to stay for adventurous travellers and those who fancy a beach in the City!

Superhost

Flat in Gold Coast

4.79 out of 5 average rating, 189 reviews

Spectacular Penthouse Corner 2BR in Streeterville

Stunning 1,200 square foot top-floor corner penthouse with oversize windows, an open layout, and dramatic city and lake views in multiple directions. This bright and modern two bedroom, one bathroom apartment is perfect for travelers looking for a stylish escape in the sky in downtown Chicago just off the Magnificent Mile and the lakefront. The building has great amenities including an amazing rooftop terrace with 360° views of the skyline and the lake. This is the best location in the city!

Top guest favourite

Home in Gold Coast

5 out of 5 average rating, 38 reviews

Gold Coast Home|Rooftop |PoolTable |Parking |Views

Luxurious Gold Coast Townhome – Offers Indoor Games, Rooftop, Parking & More! Experience the best of Chicago in this stunning 4,000 sqft Gold Coast residence. Perfect for groups of up to 12, this home features 4 spacious bedrooms, 4.5 bathrooms, and a ceiling-length window with incredible views. Enjoy a variety of indoor games and make use of the convenient rooftop. Whether you're here for leisure or work, this property offers modern amenities and unforgettable comfort in the heart of City

Flat in The Loop

4.8 out of 5 average rating, 311 reviews

Kasa | Studio, Walk to Grant Park | South Loop

It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

Guest favourite

Flat in West Loop

4.97 out of 5 average rating, 236 reviews

Comfy River West, Free Parking

Comfy, sunny 2 bedroom apt with free gated parking. Level 2 EV charging available for electric cars. Beautiful hardwood floors and high ceilings. Fully stocked kitchen with Coffee, tea and snacks. Both bedrooms have ceiling fans. Full length mirror in 1 bedroom and bath. Views of the property gardens and Willis Tower from both bedroom windows. Communal gardens, backyard has table and chairs, BBQ grill and bocce ball. An additional 2 bedroom apt in the same building may also be available.

Superhost

Flat in Near North Side

4.82 out of 5 average rating, 768 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.

Guest favourite

Flat in River North

4.89 out of 5 average rating, 47 reviews

Chic 2BR 2BA Condo with Balcony - River North Chic

Welcome to @TheDreamRentals chic 2-bedroom, 2-bathroom condo located in the vibrant River North neighborhood of Chicago! Perfectly situated in the heart of the city, this stylish and modern space offers everything you need for a comfortable stay. Whether you're in town for business, a weekend getaway, or an extended stay, our condo is the perfect home base to experience everything Chicago has to offer. We can’t wait to host you! Chicago Registration Number: R24000119721

Guest favourite

Flat in Logan Square

4.9 out of 5 average rating, 326 reviews

Bright & Lofty Bucktown 1br

My top-floor apartment in Bucktown is the perfect space for your trip to Chicago! It's a stylish, modern rehab in a classic Chicago building, so you really see the best of what the city has to offer! It's just off beautiful Holstein Park, and easy walking distance to 2 Blue Line stops - so you can get to the Loop in under a half hour! And plenty of Logan Square favorites along Milwaukee are a 15 minute walk away - book today!

Guest favourite

Flat in Old Town

4.83 out of 5 average rating, 108 reviews

Luxury Renovated Central in OldTown With Balcony

The whole group will enjoy easy access to everything from this centrally located place. There are 1 queen bed in the bedroom, 1 queen sofa bed, and 1 single pull out sofa bed in the living room area. The unit is located on 2nd floor. Inside of the unit Brand new unit with hidden lighting, expose bricks, balcony face to Schiller Street. Full kitchen if you prefer to cook.