Apartment vacation rentals in Near North Side, Chicago

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Top-rated apartment rentals in Near North Side, Chicago

Guests agree: these apartments are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Lincoln Square

4.94 out of 5 average rating, 191 reviews

Spacious, light-drenched studio-private entrance!

Sun-filled private apartment in Lincoln Square! Spacious & well-appointed studio apartment features newly renovated kitchen and 1.5 baths (spa shower!) Located in the Lincoln Square neighborhood, you’ll be steps to restaurants, cafes, pubs & shopping. Close to CTA Brown Line (Rockwell) stop, as well as Western, Foster & Lawrence buses. Just 3.4 miles to Wrigley Field. One block to Swedish Covenant Hospital. Short bus/ride-share to Andersonville, Chicago Lakefront & Foster Beach! Kid friendly.

Jul 28 – Aug 4

ﺩ.ﺇ407 per night

Guest favorite

Apartment in Chicago

4.9 out of 5 average rating, 258 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! Early Check-Ins and Late Check-Outs are difficult to accommodate.

Jan 18 – 25

ﺩ.ﺇ428 per night

Guest favorite

Apartment in Avondale

4.97 out of 5 average rating, 119 reviews

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

Jul 8 – 15

ﺩ.ﺇ442 per night

Guest favorite

Apartment in Humboldt Park

4.98 out of 5 average rating, 108 reviews

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Sep 15 – 22

ﺩ.ﺇ450 per night

Guest favorite

Apartment in West Town

4.96 out of 5 average rating, 263 reviews

Turquoise Wonder - Clean, Cozy & Stylish Apt

Clean, stylish & comfy apartment, perfect for 1 or 2 adults. 2 guest maximum, no children. Close to public transit (bus), wonderful restaurants & bars, gift shops, boutiques, coffee shops, parks, museums & more. Ukrainian Village/Humboldt Park area. King size comfortable Tempurpedic mattress. Central heat, A/C. Nice kitchen w/ stainless appliances, excellent bathroom, shower & tub. Free street parking. Relax in the comfort of the Turquoise Wonder! Enhanced cleaning protocols for COVID.

Nov 20 – 27

ﺩ.ﺇ367 per night

Guest favorite

Apartment in Roscoe Village

4.96 out of 5 average rating, 238 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

5 Star Reviews! 1 Bedroom Apartment,King Bed, queen sofasleeper, OwnOcc. Bldg. Featuring Central Air, Private Balcony, Deluxe Kitchen Stainless Steel Appliances, Microwave, & More. 55" TV, Direct TV.This outstanding Location is steps from the Roscoe Village Business District and a quick walk to the Train Stop & Bus stops, to Downtown Chicago & United Center(Hawks & Bulls).Walk to Bars, Restaurants & Shops.All stays over 30 days will require Guests to Complete additional "Lease".,

Dec 31 – Jan 7

ﺩ.ﺇ384 per night

Superhost

Apartment in Lincoln Park

4.79 out of 5 average rating, 172 reviews

Perfect 1br In Lincoln Park - Steps to Depaul!

This charming garden unit in Lincoln Park is ideally situated for any type of traveler! There are plenty of parks, dining, nightlife, and shops nearby. The main DePaul campus is just a quick walk away as well, perfect for families coming to visit their students or tour the school! You can easily take the 'El' train downtown to see all of Chicago's iconic sights. After a long day out and about in the city, come back to this cozy gem on a quiet, tree-lined street and unwind.

Feb 16 – 23

ﺩ.ﺇ610 per night

Guest favorite

Apartment in Wrigleyville

4.93 out of 5 average rating, 187 reviews

Taj Ma-small at Wrigley

I think you are just going to love my apartment. The space features wonderful large windows in both rooms and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a four-minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. It's also a walk to all of the 'Boystown' nightlife. There is no parking available with the apartment.

Feb 23 – Mar 2

ﺩ.ﺇ493 per night

Guest favorite

Apartment in Uptown

4.96 out of 5 average rating, 267 reviews

Cozy loft in Chicago's Uptown

Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; apartment on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. Andersonville (one of Chicago’s coolest neighborhood is a 15-minute stroll. CTA's Red Line/Wilson train station is 3 blocks away. Overnight street-parking decals also available for guests.

Oct 22 – 29

ﺩ.ﺇ416 per night

Guest favorite

Apartment in Gold Coast

4.89 out of 5 average rating, 140 reviews

Charming Gold Coast One-Bedroom Near Downtown!

Perfect Gold Coast studio near downtown, the lake and everything else! We are nestled in the Gold Coast in an excellent location. Public Transportation, restaurants, shops, museums and grocery stores are all steps away! The apartment is within an art deco style mid rise and has everything you need to be your home away from home while you're visiting the city of broad shoulders. Chicago Shared Housing Registration Number: R21000073420

Jan 7 – 14

ﺩ.ﺇ376 per night

Guest favorite

Apartment in Bridgeport

4.98 out of 5 average rating, 171 reviews

Bridgeport Garden Apartment

Enjoy a peaceful stay at this colorful, creative, artsy and relaxing garden unit apartment in the heart of Bridgeport. Located a few blocks away from Bridgeport's best bars and restaurants. This unit is good for couples, solo adventurers, business travelers and families (with kids). Street parking is free, and I’m readily available via phone or in person (I live a few minutes away).

Sep 16 – 23

ﺩ.ﺇ406 per night

Guest favorite

Apartment in West Town

4.89 out of 5 average rating, 473 reviews

iKlektik House Chicago / Robin

CLOSE TO THE UNITED CENTER! Bright, Sunny and Stylish one bedroom, full kitchen, balcony over looking the backyard in West Town WITH FREE STREET PARKING. Close to Wicker Park, Ukrainian Village West Town and Bucktown. The space is amazing...just read the reviews! Very cozy! There is FREE street parking. WiFi Speed has been upgraded to 1200mps!!

Dec 23 – 30

ﺩ.ﺇ504 per night