
Loft vacation rentals in North Side
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Top-rated loft rentals in North Side
Guests agree: these loft rentals are highly rated for location, cleanliness, and more.

Walk to Oak Park from a Bright Madison Street Loft
Crowned "The best in neighborhood dining" according to a 2008 Chicago Tribune readers poll, the variety of Forest Park restaurants offer something for everyone. The unit is a charming two bedroom, two bath loft a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 20 minute train ride away. The condo includes additional amenities such as: - Elevator in building •Secure front and back entrances. •One assigned parking spot in the back of the building. •Full kitchen with stainless steel appliances (stove, dishwasher, refrigerator), cookware, and dinnerware. •Granite countertops. •Two full bathrooms. The master bathroom includes a Jacuzzi tub. •Two full bedrooms. Both have queen sized beds. •Smart TV with cable access and access to Netflix. •Central Air conditioning •Working fireplace •Balcony with a view of downtown Chicago's skyline •Washer and dryer in unit. Just to the east lies historic Oak Park, which offers an array of attractions such as: •Brookfield Zoo •Chicago Architecture Foundation •Ernest Hemmingway Museum and Birthplace •Frank Lloyd Wright Home and Studio •Frank Llyod Wright’s Unity Temple •Oak Park Conservatory After soaking up some attractions in Oak Park, Chicago is only a short twenty minute train ride away, and it offers such noteworthy experiences as: •Shedd Aquarium •Architecture River Cruise •Skydeck Chicago •Navy Pier •The Field Museum •John Hancock Observatory •Adler Planetarium •Art Institute of Chicago •The Museum of Science and Industry The loft and both doors to our building have key-less entry pads. We will email you your personal entry code along with check in instructions a couple days before your arrival. Each guest is given their own personal code. Codes are programmed the day of check in and deleted shortly after check out. We are as available as you need. Centrally positioned in the Madison Street shopping and dining district, the loft is conveniently surrounded by local eateries and pubs within minutes of downtown Chicago and the United Center, and just blocks from the CTA blue line. We are located half a mile from the L - Blue Line. We are the Forest Park Stop on the blue line. The blue line will take you into the city. It is about an 8 to 10 minute walk from the loft. An Uber/Lyft ride into the city ranges from $15 to $25 and takes around 15 to 20 minutes. We are one mile from the Metra train line (Union Pacific - West). The Metra dead ends into Union Station. There are a number of Metra lines that take you to surrounding suburbs. We are also one mile from the Green Line - Oak Park Stop. The Green Line is another line on the L. The third bed is a queen sleeper sofa. There is a strict no smoking policy in our building. You can not smoke on the balcony - it will result in a $500 fine. The neighborhood is vibrant in the summer and sound can travel into the unit.
LocationValueLong stay
4.96 out of 5 average rating, 542 reviews
Modern LOFT Ukrainian Village 2nd floor
Private, Bright 2nd floor Loft with Tall Ceilings with Lots of Light. Creative Decor with Artwork and Artifacts. Relaxing and Cozy. Tree Top View of the Garden. Everything you need for a Long or Short Time Stays. Stocked Kitchenette, Modern Bath, Laundry and Fast WI-FI . Perfect for 1 or 2 for work or play. The Street is Quiet, Conveniently Located just 1 block from Bustling Division Street in Wicker Park, Downtown, the Blueline to all Airports and 1 Mile from the New Salt Shed Music 🎵 Venue
ValueLocationLaundry
4.95 out of 5 average rating, 167 reviews
Lincoln Park Light-Filled Loft
Experience this unique Lincoln Park loft where you’ll love the open concept space, the floor to ceiling windows & the conveniences of your own two level suite. A converted store-front, this space is perfect for a couples weekend in Chicago, that friends get-away, or a place to call home for your small family vacation. Walk the neighborhoods & parks, and wonder why you’re not staying longer. We call this our little gem of a find, and are excited to share it with you. We love it, so will you!
FamilyValueCleanliness
4.96 out of 5 average rating, 252 reviews
1920s fully updated unique open artist loft space
True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost
FamilyValueAir conditioning
4.89 out of 5 average rating, 194 reviews
Huge Downtown 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!
ValueLocationSleep quality
4.79 out of 5 average rating, 282 reviews
Studio with View of Skyline in Heart of Pilsen
Explore Pilsen and the beautiful City of Chicago in this unique Loft Style Studio apartment with a view of the Willis Tower and in the Heart of Pilsen. Apartment features a Roku TV with Wifi, private entrance, open layout, closet, bathtub with handheld shower head. 1 queen bed and a sofa bed couch, no kitchen but does have a fridge. Unit is on the 4th floor, no elevator. No Private Parking, just street parking only . Located near major transportation, Divvy Bike Station across the street.
FamilyValueTV
4.72 out of 5 average rating, 192 reviews
Luxury Penthouse Loft - Heart of Fulton Market
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 dedicated elevator entrance, free onsite garage parking, 5 bedrooms/3 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!
FamilyValueNearby
4.86 out of 5 average rating, 176 reviews
Tea Studio in Wicker Park Spring Factory
There's no other place like it in Chicago. A converted 1900's warehouse in the heart of Wicker Park - Once a Prohibition-era distillery, then a spring factory, and finally reimagined as a one-of-a-kind designer loft. Features soaring 14-foot timber ceilings, exposed brick, and a level of finish that earned a national kitchen award and a feature in TimeOut's "Best in Chicago". The kitchen is massive. The bathrooms are luxurious. Plus, Chicago's best neighborhood is right outside the door.
ValueFamilyLong stay
4.96 out of 5 average rating, 309 reviews
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.
ValueLocationTV
4.96 out of 5 average rating, 608 reviews
Wicker Park Loft w/ Free Parking; Easy DWTN Access
Stay in a modern 3-bedroom, 2-bath Airbnb in Wicker Park, Chicago, located at the prime intersection of North Ave & Ashland. This updated unit features stylish finishes, spacious living areas, and free on-site parking, a rare find in the city. Just 10 minutes from downtown, you’re close to top attractions, dining, nightlife, shopping, public transit, and everything Wicker Park has to offer—perfect for families, groups, or business travelers. Free designated parking to top it off.
ValueLocationCheckout
4.87 out of 5 average rating, 246 reviews
18th St Cozy and Unique 2BR Loft
Stay in our colorful and comfy Loft. Located in Pilsen, also known as ‘Heart of Chicago’. You are in walking distance to an array of restaurants from street food to fine dining. Enjoy a show at the historical Thalia hall theatre or a night at the piano bar downstairs. You’re only a five minute drive from Chinatown, Greektown and Little Italy; and ten minutes from Millenium Park. Absolutely NO SMOKING in the apartment and inside of the building‼️ Absolutely NO PARTIES‼️
ValueFamilyTV
4.87 out of 5 average rating, 104 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).
FamilyLocationAccess
4.89 out of 5 average rating, 410 reviewsPopular amenities for North Side loft rentals
Family-friendly loft rentals

Lovely Garden Studio in Chicago
LocationValueCleanliness
4.98 out of 5 average rating, 157 reviews
CT's Art BNB in West Town's Gallery Row
ValueLocationGetting around
4.96 out of 5 average rating, 157 reviews
Entire Spacious, Private Loft Apt Historic Beverly
LocationFamilyParks
4.94 out of 5 average rating, 190 reviews
New! Loft Apartment-Chicago Disinfected
ValueFamilySleep quality
4.77 out of 5 average rating, 283 reviews
Unique Roscoe Village Penthouse Loft - Hidden Gem!
LocationHospitalityIndoor spaces
5.0 out of 5 average rating, 3 reviews
Lovely three bedroom Loft , University Of Chicago
FamilyLocationWifi
4.27 out of 5 average rating, 15 reviews
Loft Style Private Apt 3 (1 Room - 420 Friendly)
LocationValueCheckout
4.82 out of 5 average rating, 39 reviews
Logan Square Blue Line • Queen Bed + Workspace
LocationValueLaundry
4.71 out of 5 average rating, 87 reviewsLoft rentals with a washer and dryer

West Town Traveler's Lodge
ValueFamilyLayout
4.85 out of 5 average rating, 681 reviews
The Wicker Park Urban Oasis-Prime Location!
LocationValueCleanliness
4.85 out of 5 average rating, 41 reviews
City Urban Loft in the Heart of Wicker Park!
LocationFamilyAccess
4.99 out of 5 average rating, 81 reviews
Spacious Modern Retreat with Unique Charm
ValueLocationComfort
4.96 out of 5 average rating, 25 reviews
Uniquely Spacious Two-Story Loft in Wicker Park
FamilyValueKitchen
4.82 out of 5 average rating, 56 reviews
Elevated, open-concept loft with industrial feel
LocationValueCheck-in
4.78 out of 5 average rating, 41 reviews
South Loop Luxury Lofts
ValueFamilyAccuracy
4.64 out of 5 average rating, 50 reviews
Architect-Designed Logan Square Loft | 15’ Ceiling
ValueLocationAir conditioning
4.89 out of 5 average rating, 422 reviewsOther loft vacation rentals

NEW! River West/West Loop Urban Oasis
LocationFamilyParking
4.86 out of 5 average rating, 14 reviews
Vintage Downtown Penthouse, Safe #6 +gym&balcony
LocationValueNearby
4.69 out of 5 average rating, 259 reviews
Spacious Downtown Penthouse | vintage, balcony&gym
ValueLocationSleep quality
4.7 out of 5 average rating, 227 reviews
South Loop Luxury Lofts
ValueLocationAir conditioning
4.74 out of 5 average rating, 39 reviews
South Loop Luxury Lofts
ValueLocationSleep quality
4.73 out of 5 average rating, 33 reviews
South Loop Luxury Lofts
ValueLocationAccuracy
4.56 out of 5 average rating, 32 reviewsDestinations to explore
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- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Naval Station Great Lakes
- Indiana Dunes State Park
- 875 North Michigan Avenue
- Six Flags Great America
- University of Chicago
- The Field Museum
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Union Park
- Frank Lloyd Wright Home and Studio
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- Donald E Stephens Convention Center
- Byline Bank Aragon Ballroom
- Washington Park Zoo
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