
Apartment vacation rentals in Near North Side, Chicago
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Top-rated apartment rentals in Near North Side, Chicago
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Popular amenities for Near North Side, Chicago apartment rentals
Weekly apartment rentals

Apartment in West Lake View
4.95 out of 5 average rating, 105 reviewsChic retreat near the best of Lakeview & Wrigley
We loved staying here. The apartment is very stylish, comfortable and quiet. Its also in a great neighborhood and the parking arrangement worked out great. We look forward to staying here again in the future. Thanks for a great time!

Apartment in Wicker Park
4.94 out of 5 average rating, 102 reviewsBright two bedroom garden apartment
We had a great stay. The place was clean and cozy. The three of us were able to explore the city and then return to relax in the garden unit. Many great places to eat in walking distance. The free and plentiful street parking was a bonus. Thanks for hosting us.

Apartment in Lincoln Square
4.91 out of 5 average rating, 186 reviewsComfortable Vintage North Side Retreat for 8
We had a great stay here - we were just a few houses from a Main Street with shops and several restaurants. A 10-15 minute walk in the other direction led us to more places. David was proactive communicating with us prior and during our stay. As stated in the listing, parking can be challenging but we managed to find parking all but one time. David had told us an app to use for parking spots and the one time we needed to use it, we had a spot for a few dollars until noon the next day. The unit size was great for our party of 5 and the home is in a quiet, safe neighborhood. We would definitely stay here again - it was less than 20 min to downtown, close to the train, close to Wrigley. Highly recommend!

Apartment in Lincoln Park
4.95 out of 5 average rating, 111 reviewsElegant Depaul Apt on Jonquil Park
This was our first time staying in an Airbnb and questions were answered quickly and kindly. We found the apartment clean, cozy, comfortable, close to many amenities, including train, and walking distance to our daughter’s apartment was convenient. We didn’t use the kitchen, except for the Keurig coffee maker and filtered water pitcher, which were nice and it was well stocked. The bed was comfortable and shower nice. Judith was a gracious host, kindly responded to text messages, and available. Thank you so much a great stay in Chicago!

Apartment in West Town
4.92 out of 5 average rating, 349 reviewsSpacious & private! Free parking! Great location!
I took a weekend just to get away from my normal surroundings. Dan's place was perfect. It was clean, peaceful, and well equipped. Dan was an awesome host. He checked in on me and I really appreciated that considering I traveled alone. I felt secure and like I had a friend nearby. I recommend this place. I would definitely stay again!

Apartment in Irving Park
4.94 out of 5 average rating, 231 reviewsCool and Modern Chicago Apartment near Transit
I had an amazing stay at this Airbnb! The location was perfect—everything in Chicago was about 20 minutes away, making it super convenient to explore. Chicago was freezing this weekend, but the host had the heater on before our arrival, and each room had an additional heater and fan available, which was such a thoughtful touch. The space itself was incredibly spacious, so everyone had plenty of room without feeling on top of each other. The bed linens were top-tier—honestly, they felt like five-star hotel quality. And the cleanliness? Spotless! Everything was meticulously maintained and aesthetically pleasing, making the apartment feel warm, inviting, and well put together. Another huge plus was the parking—it made our stay even smoother. On top of that, the host was super flexible. Our flight was in the late afternoon, and while she didn’t initially offer late checkout as an option, she was kind enough to accommodate us for an additional fee, which we really appreciated. Impressed!

Apartment in West Town
4.85 out of 5 average rating, 161 reviews*Comfortable & Spacious Home Close to Downtown*
This was a very spacious and clean apartment that comfortably hosted our family of 6 for several days. Having two separate living areas was very useful and allowed our group to spread out a bit. The full-size crib in the extension area off the master bedroom was also much appreciated as we had a 2-year-old with us. The building is on a quiet street just one block from Humboldt Park and two blocks from restaurants and shops on North Avenue. There was a grocery store within 2 blocks. Dubbs was a very responsive host, and we appreciate his flexibility with checkout time. We would happily stay here again.

Apartment in Bridgeport
4.93 out of 5 average rating, 112 reviewsCitySlickers Crash Pad /Free Parking /No Clean Fee
I loved this Airbnb, is was FULLY STOCKED, even came with hair dryer and flat iron that me and my friend totally forgot that SAVED THE DAY, also their bathroom soaps (shampoo, conditioner, body soap) smelt sooo gooddddd I was excited to get in the shower haha!!! Was a great stay, more than enough hangers and blankets to keep cozy, and the little deck outside was sweet even tho it was snowing LOL! Obv they can’t control that! 😂overall 10/10 was very content and had a blast!
Private apartment rentals

Apartment in Oak Park
4.87 out of 5 average rating, 276 reviewsCosmopolitan Nest in Oak Park North Side
Had a great stay at Zarko’s place. Located in a quaint, quiet neighborhood, he offered a comfortable and clean apartment room with a separate entrance to the house. Onsite parking was very helpful. During our short trip we didn’t meet Zarko, but he was attentive via calls and texts and gave clear instructions for parking and check in. Would definitely recommend a stay at Zarko’s!

Apartment in Near North Side
4.91 out of 5 average rating, 127 reviewsModern 3BR with Private Rooftop & Free Parking
Great space and location, short 5 min walk to the train station. Song was an excellent host and the space was modern, clean, and comfortable.

Apartment in Lincoln Square
4.79 out of 5 average rating, 289 reviewsCozy Garden-Subterranean Apartment
Great place and neighborhood. The place was definitely cozy and matched exactly what the listing described.

Apartment in East Rogers Park
4.9 out of 5 average rating, 142 reviewsPrivate Garden Apartment GATED FREE Parking
Elena’s cozy basement suite was very clean and reasonably priced for being so close to both Chicago and Evanston. Private parking was an added gift. The bed was comfortable and all of the linens smelled fresh.

Apartment in Avondale
4.98 out of 5 average rating, 103 reviewsLovely 2bedroom 1bath Apt and outdoor seating.
Great home in a great area! We loved the house it was just what we needed for our trip to Chicago.

Apartment in Logan Square
4.8 out of 5 average rating, 138 reviewsWelcome Chez Moi
Nice place, right around the corner from the Constellation music venue -- that is why I came here. The place was vey convenient and nice. Parking was pretty easy.

Apartment in Avondale
4.91 out of 5 average rating, 269 reviewsAvondale Gem: 2BR, Stylish Kitchen, Transit Nearby
Our stay was wonderful. We arrived in Chicago 20 minutes before check in and Shawn was responsive and let us in early so we didn't have to stand in the cold! Wonderful location to fun bars, good breakfast spots, and an easy walk to the blue line! Thank you!

Apartment in Roscoe Village
4.75 out of 5 average rating, 254 reviewsNorth Side Pied-à-terre
This cute apartment is right on Roscoe Street in the heart of Roscoe Village. Everything nearby is very walkable, and a train stop is just a few blocks away.
Apartment rentals with a hot tub

Apartment in West Loop
4.83 out of 5 average rating, 75 reviewsQuiet but in the Heart of City walk Everywhere
Wonderful stay. Location was perfect for what we needed. The space was clean and comfortable. Would recommend for sure.

Apartment in The Loop
4.89 out of 5 average rating, 37 reviewsThe Areal Oasis
Had a great stay at such a great location. Coffee and food all within a few blocks walk, plus a target on the corner incase you forgot anything like we did 😅. Stephanie was helpful and responsive and sets up place for easy check in and out. 100% would look to stay here again!

Apartment in West Rogers Park
4.85 out of 5 average rating, 60 reviewsSpacious Beautiful Condo
Very responsive homeowners, the rooms were left with plenty of accommodations such as towels, pots and pans, a Keurig, etc. The place was left to us very clean and ready for our group upon arrival.

Apartment in Lake View
New place to stayLakeview Apt Sleeps 6 - Games - Minutes to Wrigley
Had a fantastic stay! The location was perfect—so convenient to everything we wanted to do. The space itself was spotless and well-maintained, making us feel right at home. We especially loved the amenities, which were thoughtful and really added to our comfort. The deck was absolutely beautiful—has potential for the summer. Highly recommend this place to anyone looking for a great stay !

Apartment in West Loop
4.96 out of 5 average rating, 23 reviewsSkyline Oasis: City & Lake Views
One of the most understanding and responsive hosts I have had the please of dealing with. Beautiful space, safe area, walking distance to store and bank. Parking available in structure but at a cost. 10/10 recommend.

Apartment in Belmont Cragin
4.99 out of 5 average rating, 87 reviewsBelmont Pleasures - hot tub / arcade gaming room
Nassa was a warm, responsive, and wonderful host. We had an incredible time, had everything we could possibly need and when there was a TV issue, Nassa ventured out in the cold to help us. Great place!!!!

Apartment in Irving Park
4.9 out of 5 average rating, 21 reviewsCozy 2Bed 2Bath with Parking, Balcony &Jacuzzi
From start to finish, our stay at Megan’s place was wonderful! The apartment was exactly as described clean, comfortable, and in a decent location. Megan was incredibly helpful, offering fantastic advice on things to do and where to eat in Chicago. She responded to our questions quickly, almost like our personal tour guide, and went above and beyond to ensure we had everything we needed. We’d highly recommend staying here.
Quick stats about apartment rentals in Near North Side, Chicago
Total rentals
970 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
25K reviews
Family-friendly rentals
330 properties are a good fit for families
Pet-friendly rentals
550 properties allow pets
Rentals with a pool
470 properties have a pool
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