Loft vacation rentals in Near North Side, Chicago

4.86 out of 5 average rating, 646 reviews

West Town Traveler's Lodge

Come and stay at my gorgeous 2 bedroom 1 bath condo! It's in a wonderful neighborhood, and in an ideal location for hopping around the city. It's a perfect place to re-energize between big city adventures -> just a 7-10 min walk to the Division St Blue Line Station (3 stops to The Loop). Hardwood floors, granite counter tops, high ceilings, a large back patio, some cool furniture, and exposed brick await in this charming West Town loft. Easy access to both airports via public transit is a plus!

4.87 out of 5 average rating, 109 reviews

Loft in West Loop

Luxury Fulton Market Penthouse Amazing City Views

NEW PENTHOUSE LOFT IN FULTON MARKET! Enjoy your own private luxury loft in Chicago's bustling Fulton Market-the city's center of main nightlife, restaurants and cultural scene. This 3,500 square foot penthouse features 12 foot open lofted ceilings, a personal home gym w/ Peleton+, free onsite garage parking, 4 bedrooms/4.5 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

4.77 out of 5 average rating, 232 reviews

Loft in The Loop

Fun Dtown Penthouse #4 | Park, Museums +gym

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ It's Unique! ✅ High loft ceilings ✅ FAST WIFI ✅ Spacious layout ✅ Comfy beds ✅ Central Location ✅ Private Balcony! ✅ Close proximity to Grant Park, Soldier Field, Museums, and more! You are a short walk to Millennium/Grant Park, Skydeck, Shedd Aquarium, Adler Planetarium & many dining + shopping options!

4.78 out of 5 average rating, 554 reviews

Wicker Park Loft - Walk To Everything!

Walk to Bucktown & Wicker Park bars, restaurants & shopping from this large apartment in working artists' building. 10 minute WALK to CTA Blue line TRAIN. FREE STREET PARKING. Premium mattresses and all essentials provided. Resident artists work on the first floor of this historic former telephone repair and switching station. Very laid back vibe. NOTE All guests must be on your reservation for an accurate $total. There is a $30 per night/ per guest charge AFTER 2 Guests (3rd to 5th)

4.88 out of 5 average rating, 387 reviews

Loft in Logan Square

Modern, Open, Logan Square Loft w/ Unique Design

Welcome to our open concept studio loft. Located in the heart of Logan Square, we are walking distance to Palmer Square Park, plus some of the cities best coffee shops, restaurants, galleries and summer festivals. This space is airy, naturally lit, and comfortable with a 15' floor to ceiling main atrium, full height windows and custom architectural light screen plus all the amenities to make your stay comfortable. Easy access to public transportation makes getting around the city a breeze

Loft in Pilsen Historic District

4.9 out of 5 average rating, 390 reviews

Pilsen Modernist, Creative, Lightfilled Loft

Take morning drinks through the sunshine-yellow room to the back porch, or watch light dance on translucent walls and glossy black and white hardwood floors. Eclectic design includes a mix of new and vintage furniture, and a collection of art and design books for guests to enjoy. This unit is owned by an artist couple who split their time between Tucson, AZ and Chicago. This is their personal unit when they're in Chicago. Come stay here to get away, be comfortable, relax, and be inspired.

4.96 out of 5 average rating, 507 reviews

Loft in Lake View

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

4.89 out of 5 average rating, 137 reviews

Entire Loft in Heart of Wicker Park with Parking

Entire floor in one of the coolest neighborhoods of Chicago. You will have access to whatever you desire right here, from it’s amazing abundance restaurants, shopping and cafes to walking the almost three mile walkway of the “606” and it’s rotating installations, observatory and relaxed vibe. At the end of your day you’ll love heading back to your wide open space with its retro inspired furnishings with just the right amount of modern amenities and comfort.

4.82 out of 5 average rating, 251 reviews

Loft in Logan Square

Quirky Bucktown Loft w/ Parking No Parties

Located on a peaceful treelined street in energetic, fashionable Bucktown with upscale amenities at your fingertips. This unique penthouse/loft apartment has its share of quirks that come with being a 125-year-old building yet its unique vintage comfort, eclectic furnishings and modern necessities come together to make your time in the city relaxing and unforgettable. This is a legally licensed Chicago vacation rental R22000079930

4.89 out of 5 average rating, 351 reviews

OHC Gorgeous Huge Studio Apt Steps to Blue Line

Welcome to OHC Studio! Part of the Open House Contemporary family of art gallery airbnbs, this huge 1000 sq ft studio apartment is the perfect place to call home base while you explore Chicago. Featured in Architectural Digest (Aug. 2018) and as one of Bobby Berk's (Queer Eye's designer extraordinaire) top 10 Airbnbs in Condé Nast Traveler (Sept. 2018).

4.96 out of 5 average rating, 253 reviews

Tea Studio in Wicker Park Spring Factory

Welcome to the Tea Studio where you'll create gourmet meals in an immaculate professional grade kitchen. Relax in a one-of-a-kind former spring factory with Chicago's trendiest neighborhood at your doorstep. Sip rare teas and indulge in the sophistication of this Asian-industrial loft. Detox after a long day in a stainless Japanese soaking tub.

4.89 out of 5 average rating, 289 reviews

Bright & Spacious Noble Square Loft

Bright and spacious top floor loft in Chicago's Noble Square neighborhood. Walk to food, drink, fun and shopping. Easy access to ZipCars and public transportation (bus, train, and METRA). Quick trip to Michigan Ave, Lakefront and Navy Pier. A quick 5 minute ride to nightlife in the Wicker Park / Bucktown neighborhood.

Vacation rentals for every style

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Popular amenities for Near North Side, Chicago loft rentals

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Free parking on premises

Air conditioning

Family-friendly loft rentals

4.81 out of 5 average rating, 144 reviews

Loft in Near West Side

SPACIOUS and VERY BRIGHT 2BDR LOFT near DOWNTOWN

WendyRating, 5 stars1 week ago

We had a girls trip and stayed at this Airbnb and we absolutely loved it! Very clean and it looks better than the photos :) we felt safe inside, it’s spacious, clean and a great deal! If I ever come back with a big group, I’ll consider staying here again.

Private room in Bridgeport

4.83 out of 5 average rating, 48 reviews

Sunny Spacious Artist Yoga Loft

SeverineRating, 5 stars1 month ago

GuruNischan’s place felt right at home. Friendly, communicative, respectful, both her and her roommate Jose, made my stay a very relaxing experience. The place is clean and quite, I would happily recommend and book again !

Private room in River North

4.88 out of 5 average rating, 956 reviews

Artist Loft, Private Room

FasekaRating, 5 stars2 weeks ago

This is the perfect location for bars and restaurants! It is also in walking distance to public transport which was wonderful! Michael was friendly and helpful! He was in and out of the unit during our stay. The unit is not as clean and organized as pictured but it is beautiful and everything you can expect of an artists loft. Lots of plants, art and collectibles. Would recommend for your next stay in Chicago!

4.75 out of 5 average rating, 65 reviews

Private room in Evanston

Beautiful Space in Evanston Chicago Bungalow

AnnaRating, 5 stars6 months ago

Lovely space for a small family. Nice to be by a park, quiet area and close to major streets as well. Peaceful and nice stay!

4.93 out of 5 average rating, 107 reviews

Urban Glamour in West Town

GaylaRating, 5 stars2 weeks ago

Lots of space at this Air B&B! It was well equipped for our party of three, and in an excellent location close to restaurants and shops. The neighborhood was walkable and nice and the other residents in the building were very friendly!

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Loft rentals with a washer and dryer

Loft in Pilsen Historic District

4.9 out of 5 average rating, 30 reviews

18th St Cozy and Unique 2BR Loft

SallyRating, 5 stars3 weeks ago

Very comfortable and quiet. Great furnishings and style. Perfect location for us on 18th street

Loft in Lincoln Park

4.71 out of 5 average rating, 24 reviews

Amazing 2500 sq/ft Loft & Bungalow in Lincoln Park

BlakeRating, 5 stars22 months ago

Great place to stay! Adamm was very responsive to every question I had. Also, it’s a very close drive/walk to a lot of places so you can truly experience a Chicago vibe. Highly recommend!

4.94 out of 5 average rating, 18 reviews

City Urban Loft in the Heart of Wicker Park!

NikitaRating, 5 stars1 week ago

Everything described and more! Clean, under a 5 min walk to 4 coffee shops, train and bus station and shopping options. Michael was very warm, welcoming and responsive. This Airbnb made a birthday trip to Chicago really special! 🥰

Top guest favorite

Loft in Forest Park

4.96 out of 5 average rating, 506 reviews

Walk to Oak Park from a Bright Madison Street Loft

DaleRating, 5 stars2 weeks ago

It was a great experience. Plenty of restaurants in the area. Also you have a grocery store and Trader Joe’s very close by. The hosts were very responsive to all our questions. It was a great experience. Thanks again for a wonderful experience!!! Jordon and Jeremy are great hosts!!!!! Five Stars

4.93 out of 5 average rating, 205 reviews

Trendy Wicker Park Loft with Parking

HeidiRating, 5 stars1 month ago

Our families got together for a long weekend in Chicago and we wanted to stay in a hip neighborhood with walkable restaurants/shops but also wanted somewhere close enough to downtown Chicago so we could take the train or make the quick drive. We also needed a place that could accommodate 4 adults and 4 young kids (ages 1-7). George’s place checked these boxes for us. We read a few reviews prior about noise, and while you can definitely hear street noise in the living room, we didn’t have any issues sleeping. The kitchen was stocked which was helpful for cooking breakfast in the morning. We were pleased to find a few baby gates for the 1 year old to block the steep stairs. The Hyatt next door has a fun roof top bar that was also kid friendly. Our kids also enjoyed a park/playground a couple blocks north. There is one parking space, so we did opt to use Spot Hero for the other car and found one decently close. The neighborhood has so much to check out, we’d definitely stay again!

4.89 out of 5 average rating, 112 reviews

Loft in Brookfield

1920s fully updated unique open artist loft space

KrisRating, 5 stars2 weeks ago

this place is a dream space. complete in awe of everything that went into the place. very easy to get to. easy to communicate with the host. even the neighbor next door was friendly. would recommend, would book again.

Loft in West Loop

4.75 out of 5 average rating, 120 reviews

Fulton Market Industrial Modern Designer Loft

ShaneRating, 5 stars8 months ago

Great stay, excellent neighborhood and surroundings. Would stay here again!