Apartment vacation rentals in Near North Side, Chicago

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Popular amenities for Near North Side, Chicago apartment rentals

Weekly apartment rentals

Guest favorite
A modern kitchen with dark wood cabinetry and granite countertops is complemented by stainless steel appliances. A large island with seating for six is positioned next to a dining area featuring a round table for four. Views of the lake are visible through the windows.
Apartment in Magnificent Mile
5 out of 5 average rating, 8 reviews

Luxury Designer Penthouse NW | Pool | Gold Coast

ReginaRating, 5 stars2 weeks ago
Beautiful apartment in Chicago’s Gold Coast area - lots to do, easy walking distance to shops, restaurants and Oak Street Beach (and a view of the beach from the dining room). Well appointed building with a rooftop pool, gym and lounge. Quiet neighbors on the floor.
A modern living space features a combination of comfortable seating arrangements, including a sleek sofa and various chairs. Bright natural light floods the area, highlighting a stylish dining table and a mounted television. Contemporary art and decorative elements add to the inviting ambiance.
Apartment in West Loop
4.8 out of 5 average rating, 322 reviews

Sophisticated River West 2 Bedroom - Near the L

BharadwajRating, 5 stars1 week ago
The apartment was clean, and the amenities were exactly as described. It also provided a good-quality air mattress that comfortably accommodated an adult. The only area for improvement would be the air conditioning, as the fan can be quite loud when in use.
Superhost
A modern living area features exposed brick walls and large windows allowing ample natural light. A dark sofa is complemented by decorative pillows in teal, while a wooden coffee table occupies the center. A stylish bookshelf holds decorative items and a work desk is positioned nearby.
Apartment in West Town
5 out of 5 average rating, 4 reviews

Modern & Spacious Condo Minutes from the Loop

AlanRating, 5 stars2 weeks ago
Absolutely loved our stay. Great location! Super comfortable beds. Slept like a baby. Felt like home. Parking felt very secure. No problems at all. We will look forward to staying here again!
A bright living area features large windows allowing natural light to fill the space. Two armchairs with brown leather seats are positioned beside a modern coffee table. A dark rug with a geometric pattern contrasts against the light walls, while plants add a touch of greenery.
Apartment in Gold Coast
4.79 out of 5 average rating, 186 reviews

Spectacular Penthouse Corner 2BR in Streeterville

JuanRating, 5 stars2 weeks ago
The apartment was clean, comfortable, and had everything I needed. The location was perfect—close to everything downtown, and the view was a really nice bonus. Overall, a very enjoyable stay! .
Guest favorite
An open living area features a modern kitchen with stainless steel appliances and granite countertops. A dining table with seating for four is positioned next to a cozy seating area, which includes a large sofa and wall-mounted TV. Natural light filters through the windows.
Apartment in Old Town
4.98 out of 5 average rating, 47 reviews

Old Town Tranquility (+parking)

SusanRating, 5 stars3 weeks ago
Nicole & Matt were responsive, kind, & timely communicators! Their special oasis was artistically beautiful & comfortable in a walkable, safe & vibrant space! We met a neighbor who taught us all about the neighborhood's unique history! We loved traveling all over Chicago in this home away from home! You will, too!
Superhost
A distinctive brick building is featured, showcasing an art deco facade and ornate fire escapes. Large windows line the upper floors, while a storefront with glass doors occupies the ground level, displaying signage for the South Loop Club. Urban surroundings are visible.
Apartment in The Loop
4.74 out of 5 average rating, 31 reviews

South Loop Studio Hotel(205)

StephanieRating, 5 stars4 weeks ago
I really enjoyed the hospitality provided, this is a great place to stay for a quick weekend trip in the city! Walking distance from everything.
Guest favorite
A bright living area features floor-to-ceiling windows showcasing a skyline view. The muted colors of the comfortable sofa and accent chairs create a calming ambiance. A small side table sits next to an armchair, illuminated by natural light.
Apartment in West Town
5 out of 5 average rating, 9 reviews

Luxury 2BD/2BA High Rise with Views, Gym, Rooftop

ViyadaRating, 5 stars2 weeks ago
The unit looks better than what we’ve expected. The room is clean and neat. The apartment is also closed to the city center, which allow us to easily access many tourist attractions. Christian is also very friendly host and willing to help you out with anything.
The updated kitchen features sleek white cabinetry and countertops complemented by modern appliances. Two white bar stools are positioned at the island, and an artistic light fixture hangs above. A window allows natural light to brighten the space.
Apartment in Lincoln Park
4.74 out of 5 average rating, 218 reviews

Rare, Updated 1 BR Condo in Lincoln Park!

AbhijitRating, 5 stars2 weeks ago
We had a wonderful stay! The place was spotless and exactly as described. The location was perfect—close to everything we needed. The hosts (Sarah and Brandon) were very communicative and helpful throughout our stay. We had let them know something was missing when we arrived late at night, and it was thoughtfully placed outside the door by morning. Overall, a great place to stay—highly recommend!

Private apartment rentals

Superhost
The open-concept living area features a modern kitchen with stainless steel appliances and a large island with seating for four. A cozy seating area includes dark wood furniture and a flat-screen TV mounted on the wall, complemented by warm wood flooring and soft lighting.
Apartment in West Ridge
5 out of 5 average rating, 30 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

ElizabethRating, 5 stars5 days ago
This is a charming and very comfortable unit. All the amenities are thoughtful and more generous than most other AirBNBs that I’ve stayed. We found the location very convenient to family and Northwestern U, and even getting downtown. The unit was spotless, clean and organized. And exceeded our expectations. Being able to park in the garage was a huge benefit for us. We had a busy schedule with leaving in the morning and not getting back until later evening. It was so nice not to have to search for street parking and not have that worry. We very much enjoyed our stay. This will be our “place” when we return. Elizabeth
Superhost
An open living area features a comfortable sofa and stylish accent chairs, arranged around a glass coffee table. A large flat-screen TV is mounted on the wall, reflecting the light from the expansive windows that provide a view of the exterior building and greenery.
Apartment in River North
4.87 out of 5 average rating, 38 reviews

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

CassandraRating, 5 stars4 weeks ago
Wonderful place and the host was amazing. Definitely staying here again the location was awesome and the apartment was beautiful .
Superhost
A modern kitchen is showcased, featuring sleek cabinetry in dark tones and stainless steel appliances. An island with a light countertop provides ample space for meal preparation. Natural light enters through large windows, brightening the inviting atmosphere of the open layout.
Apartment in Pilsen Historic District
4.94 out of 5 average rating, 52 reviews

Pilsen Modern Chic Retreat

KennaRating, 5 stars1 day ago
Our group had a wonderful stay at this listing! The host, Carmen, was very responsive and informative with answering our questions. The property itself was easy to locate with and the unit very spacious and nicely decorated.
Superhost
A cozy living area showcases a navy blue sofa facing a decorative fireplace and a wall-mounted television. Two armchairs and a round dining table create a functional seating arrangement. Natural wood flooring and built-in shelves enhance the spacious feel, complemented by greenery throughout.
Apartment in Lincoln Park
4.88 out of 5 average rating, 218 reviews

Lincoln Paradise– Steps to Park & Zoo!

JeanneRating, 5 stars1 day ago
Our second stay here-- all is wonderful!! Well appointed space, fabulous bed and pillows. Everything you need is in the kitchen. The location cannot be beat -- across the street from the park. Would absolutely come again!!
Superhost
The master bedroom features a spacious bed with a tufted headboard and soft, neutral bedding. Two nightstands with lamps are on either side, and a television is mounted on the wall. Natural light filters through the wooden blinds, enhancing the warm wooden floors.
Apartment in Old Town
4.93 out of 5 average rating, 209 reviews

OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)

AndreaRating, 5 stars2 weeks ago
From booking to check out Wendy and Matt communicated with me every step of the way. Very responsive, helpful, and friendly. The Airbnb is just as described and is absolutely beautiful, but also comfortable and homey. They have thought of everything. My husband and I both had to work some and the desk set up with extra large monitors was the best surprise! The location is perfect-walkable to some really fun restaurants. We went to Happy Camper, Small Cheval, and Mr. Gyros. The red line is right around the corner and we felt very safe walking the neighborhood after dark. You will meet many people on the street with friendly dogs :) The ability to park our car off the street was also one of the best perks of this place! Our family couldn’t have picked a better place to spend our time in Chicago. Thank you Matt and Wendy!
Superhost
An open living space is visible, featuring a cozy seating area with a brown couch and two green armchairs. A large area rug adds warmth beneath the coffee table. A kitchenette area with wooden counter space and modern appliances is present, while bookshelves display various books and decor.
Apartment in Near West Side
4.88 out of 5 average rating, 94 reviews

Garden on Warren

AliviaRating, 5 stars4 days ago
David was super kind and helpful throughout our stay. He responds immediately and had clear instructions and communication. The apartment was beautiful and had lots of amenities. The price was also very reasonable for the location. I would definitely recommend this place to anyone!
Superhost
A bedside table features a stylish lamp with a woven shade emitting a warm glow. A decorative vase filled with dried floral arrangements adds texture and interest. The cozy bed is adorned with soft linens, creating a serene sleeping environment.
Apartment in Irving Park
4.98 out of 5 average rating, 64 reviews

Pine Beam Sloth Apartment next to Blue Line

KristinaRating, 5 stars5 days ago
The apartment was impeccably clean. Was traveling for business had everything needed. It is loft style with open bedroom ceiling. Restaurants nearby
Superhost
The living and dining area is designed with high ceilings and an open layout. A sofa is paired with a modern armchair, while a wooden dining table is surrounded by stylish chairs. Large windows bring in natural light, highlighting warm wood floors and minimal decor.
Apartment in Magnificent Mile
4.94 out of 5 average rating, 254 reviews

Urban Chic Apartment by the Magnificent Mile

AndrewRating, 5 stars2 weeks ago
Perfect location near Michigan, the river and the lake. Lovely apartment with great light. Although its located directly above a bar, there were no issues with noise. Would definitely stay here again for future trips back to Chicago

Apartment rentals with a hot tub

Superhost
An open-concept living and dining area is showcased with a gray sectional sofa and a wooden coffee table. A modern ceiling fan hangs above, and natural light fills the space. A dining table with six chairs is positioned nearby, adjacent to a sleek kitchen.
Apartment in West Rogers Park
4.85 out of 5 average rating, 79 reviews

Spacious Beautiful Condo

SophiaRating, 5 stars5 days ago
We came for our daughter’s graduation and stayed a few extra days to tour the city. This place was perfectly located for both occasions. It was much more spacious than we expected, and everything was very clean. We especially appreciated the fresh towels and beddings. Our only wish is that the beds were a bit larger, especially the double bed, which would be more comfortable for a couple if it were at least a queen size. That said, the beds were very comfortable. Overall, we had a wonderful stay - definitely one of our best Airbnb experiences!
Superhost
A bright and airy living area is filled with natural light from floor-to-ceiling windows, offering expansive city views. A plush sectional sofa is positioned on a soft area rug. Potted plants and a console with a television add to the inviting ambiance.
Apartment in West Loop
4.96 out of 5 average rating, 27 reviews

Skyline Oasis: City & Lake Views

NatalieRating, 5 stars3 weeks ago
Perfect weeklong stay in Chicago! The apartment is well equipped and makes you feel right at home. The building is connected via sky bridge to Jewel making it easy to grab groceries. The location cannot be beat - easy access to West Loop, Wicker Park, River North. The hosts were fantastic and flexible with our check in times. Looking forward to coming back!
Superhost
The living area features a light-filled open layout with floor-to-ceiling windows. A plush sectional sofa is complemented by two stylish lounge chairs. A low coffee table sits on a modern area rug, with a decorative plant adding a touch of greenery to the space.
Apartment in West Town
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars1 month ago
We stayed with my family for 3 days n loved the place it's ambience, cleanliness, very well equipped with all the necessities.....this place definitely feels like home and the hosts are very kind and quick with there response. Wherever in future I am coming to chicago shall book this place.
Superhost
A living area features two sofas and a coffee table centered on a colorful area rug. Warm lighting emanates from two table lamps beside the sofas. Artwork adorns the wall, enhancing the cozy ambiance of the space.
Apartment in Chicago
4.88 out of 5 average rating, 16 reviews

Large Studio Apartment with no cleaning fee

Latrice Rating, 5 stars1 week ago
David and his co-host were excellent. Our family enjoyed our stay. We used to live in the Bronzeville area and love the new additions to the neighborhood. Everything met or exceeded our expectations.
Superhost
A modern living area features a green tufted sofa in the foreground, accompanied by a dining space with a round table and several chairs. Large windows offer expansive skyline views, allowing natural light to fill the space. Minimalist decor elements add a contemporary touch.
Apartment in West Loop
4.83 out of 5 average rating, 119 reviews

Penthouse Near Fulton: Skyline, Spacious

ValerieRating, 5 stars2 weeks ago
SPECTACULAR!! This space is how you should visit Chicago. Breath taking views from this 33rd floor luxury penthouse apartment lives up to the hype. Our family of six were extremely comfortable in this 3 bedroom/3 bath unit. And for a person that likes cooking, the kitchen is spacious. Don’t pass on seeing Chicago from the views in this beautiful apartment.
Superhost
The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.
Apartment in Belmont Cragin
4.98 out of 5 average rating, 119 reviews

Belmont Pleasures - hot tub / arcade gaming room

AustinRating, 5 stars1 week ago
Stay was great and Mariam was a super host. The space was exactly as pictured and all the games were a blast. Miriam even checked in a couple times to make sure we had everything we need and that we were having a good time. For sure would stay here again.
Superhost
A private balcony features wooden decking and a wooden railing. Two black wicker chairs with cushions and a matching coffee table create a cozy seating area. Potted plants hang from the railing, and the surrounding neighborhood is visible in the background.
Apartment in Irving Park
4.92 out of 5 average rating, 36 reviews

2Bed 2Bath 15min to Wrigley with Parking& Balcony

AlexRating, 5 stars1 week ago
Clean and cozy home with a friendly host!
Superhost
An open and spacious living area features a white sectional sofa and unique cow print coffee table. The dining space is equipped with round chairs, and a modern kitchen is visible in the background. Light streams through frosted glass block windows, enhancing the airy atmosphere.
Apartment in West Town
4.87 out of 5 average rating, 461 reviews

Checkerboard Studio, Private Outdoor Hot Tub, Yard

ChanningRating, 5 stars3 weeks ago
A great property, easy enough to get in and out of the city! The hot tub was an added bonus!

Quick stats about apartment rentals in Near North Side, Chicago

  • Total rentals

    1K properties

  • Nightly prices starting at

    ﺩ.ﺇ37 before taxes and fees

  • Total number of reviews

    27K reviews

  • Family-friendly rentals

    350 properties are a good fit for families

  • Pet-friendly rentals

    570 properties allow pets

  • Rentals with a pool

    540 properties have a pool

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