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, 313 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.

Top guest favorite
A spacious rooftop patio features a built-in bar with seating for four, surrounded by lush greenery and expansive city skyline views. Strung lights provide ambient lighting, and the comfortable wood decking enhances the relaxing outdoor space.
Home in Downtown Chicago
4.99 out of 5 average rating, 104 reviews

Private Downtown Retreat with Rooftop Oasis

Welcome to your exclusive retreat in the heart of the city, where urban sophistication meets unparalleled comfort. Nestled in between Magnificent Mile and Gold Coast, this luxurious Airbnb offers a haven of style and tranquility amidst the hustle and bustle. The rooftop patio offers incredible views of the city skyline, with touches of lush greenery. The spacious living areas boast oversized windows that flood the space with natural light. Each bedroom is a sanctuary where luxury meets comfort.

Top guest favorite
A private patio features a modern three-seater sofa and a circular coffee table. Large windows from the neighboring building rise alongside, showcasing a view of the urban surroundings, while a potted plant adds a touch of greenery.
Apartment in Downtown Chicago
4.94 out of 5 average rating, 108 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.

Superhost
Apartment in Downtown Chicago
4.81 out of 5 average rating, 1,000 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.

Top guest favorite
The iconic Water Tower building is viewed at night, illuminated with warm lights, showcasing its historic architecture. In the foreground, a horse-drawn carriage is visible, adding to the charm of the scene, while modern skyscrapers rise in the background.
Apartment in Downtown Chicago
4.93 out of 5 average rating, 115 reviews

2br/2ba, A+ location by Mag mile, views & spacious

Unbeatable location next to Water Tower Place, with lots of natural light and partial lake view in a quiet vintage building with lots of character. Walk to nearly any attraction in central Chicago. I'm happy to help with sightseeing advice and discounts on popular tourist attractions. (Guests love: Location, View, Comfortable room and bed, Friendly/helpful host, Flexible luggage policy) Please see Airbnb listing 12323073 for additional reviews of this apartment.

Top guest favorite
Apartment in Downtown Chicago
4.94 out of 5 average rating, 286 reviews

Urban Chic Apartment by the Magnificent Mile

Ideally located just half a block from Michigan Avenue, this bright and open 3rd floor apartment boasts thoughtfully appointed rooms for your comfort so will have everything you need to enjoy your stay in style! PLEASE NOTE: 3rd floor walk up (NO ELEVATOR) There is a small neighborhood bar on the second floor of the building. They are respectful of our neighbors, however they do play music which can be heard in the living room but rarely in the bedrooms.

Top guest favorite
A spacious living area features warm wooden flooring and exposed brick walls. A comfortable sofa is positioned near two elegant table lamps, with a large window providing natural light. A flat-screen TV is mounted on the wall opposite, creating a welcoming atmosphere.
Guest suite in West Town
4.88 out of 5 average rating, 199 reviews

The Huron Haven

A beautiful, one-of-a-kind, hidden gem in the heart of River West. Private entry. Front & Back Patios. Full office space. Large Living Room. Exposed brick walls, 11.5’ tall ceilings. Large barn doors lead from the living room / office to a large master bedroom with large modern bathroom. The bedroom has French doors which open to private balcony with a beautiful back patio, dining space, and thriving garden. On Property Parking

Top guest favorite
The exterior of the Walton Residence showcases its historic architectural style, featuring a stone façade with intricate detailing across multiple levels. Large windows allow for natural light, and a canopied entrance is present at street level, offering a welcoming entrance amid the bustling city.
Apartment in Downtown Chicago
4.94 out of 5 average rating, 143 reviews

Urban Oasis in Vibrant Gold Coast

Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, we are perfectly situated in the middle of the action for your Chicago adventure. ***Please note that from March until the end of September 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***

Superhost
The exterior of a vintage multi-family building is highlighted, featuring intricate stonework and large windows. Decorative elements are present on the façade. A welcoming entryway with warm lighting can be seen, framed by lush green trees that enhance the surrounding environment.
Apartment in Downtown Chicago
4.82 out of 5 average rating, 102 reviews

The Rossa - Chic Studio by Mag Mile & the Lake

A design lover's dream. Spend your next trip (or staycation) in a beautifully remodeled luxury studio in Chicago's Gold Coast neighborhood. This listing is for a private studio in a multiple-unit building. ✔ Safe and vibrant neighborhood. ✔ Steps from Michigan Avenue, luxury shops, and the Lake ✔ Convenient parking options nearby. ✔ Easy self-check-in.

Guest favorite
Apartment in Downtown Chicago
4.89 out of 5 average rating, 159 reviews

Breathtaking & Chic Oasis Loc in Desirable Old Twn

Enjoy a stylish experience at this centrally-located place. Our stylish 1-bedroom Airbnb, catering to all kinds of travelers. Whether you're looking for a restful stay, a productive workspace, a central hub to explore Chicago, a night of fun at the bars and nightlife, or a snug spot to unwind and connect, our place has everything you need.

Guest favorite
The spacious living area features a modern sectional sofa with accent pillows, positioned near floor-to-ceiling windows offering panoramic views of the city skyline. A sleek coffee table displays decorative items, while a fully equipped kitchen with stylish bar stools is visible in the background.
Apartment in Downtown Chicago
4.93 out of 5 average rating, 115 reviews

Gold Coast Luxury: 2BR with Sweeping City Vistas

Stay in 'The Addams,' a prime 2BR with skyline views and a balcony, ideal for those seeking a memorable Chicago experience. You can expect a 5-star stay with us. That's a promise backed by our 97% 5-star guest rating since 2023.

Top guest favorite
A row of historic brick townhouses is presented, showcasing a symmetrical façade with large windows and red front doors. Each unit features wrought iron railings leading up to the entrance, set against a clear blue sky.
Condo in Lincoln Park
4.95 out of 5 average rating, 133 reviews

NEW luxury Old Town 1-Bedroom condo

Completely renovated 1-bedroom private condo. A five minute car ride to get downtown, steps to the lakefront. Chicago Registration Number: R24000113487

Popular amenities for Near North Side vacation rentals

Quick stats about vacation rentals in Near North Side

  • Total vacation rentals

    Explore 1,660 vacation rentals in Near North Side

  • Nightly prices starting at

    Near North Side vacation rentals start at G$2,092 GYD per night before taxes and fees

  • Verified guest reviews

    Over 54,040 verified reviews to help you choose

  • Family-friendly vacation rentals

    610 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 880 rentals that welcome pets

  • Vacation rentals with a pool

    740 properties feature pools

  • Rentals with dedicated workspaces

    1,080 properties have a dedicated workspace

  • Wi-Fi availability

    1,650 of Near North Side vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Near North Side rentals

  • 4.7 Average rating

    Near North Side stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Near North Side's top spots, include 875 North Michigan Avenue, Chicago Riverwalk, and Museum of Contemporary Art Chicago

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