Serviced apartment vacation rentals in The Loop

Find and book unique serviced apartment rentals on Airbnb

Top-rated serviced apartments in The Loop

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

1 of 1 pages1 / 1
Guest favourite
A bright living area features large windows allowing natural light to fill the space. A comfortable sofa with colorful cushions faces a coffee table, while an entertainment unit with a television adds convenience. Decorative wall art enhances the inviting atmosphere.
Apartment in Roscoe Village
4.91 out of 5 average rating, 327 reviews

A+Chicago Roscoe Village Entire Home Wrigley+ More

Elegant large bright posh eclectic flat in heart of Roscoe Village very comfortably furnished to enjoy charismatic Chicago. Free parking. Very fast internet and laptop comfortable space for your home office. Professionally cleaned, well appointed cozy, perfect for families or a solo traveler. Fab decor, fully stocked kitchen plus all amenities and an open-plan layout invites you to enjoy quiet elegant comfort of home. Easy walk to Wrigley Field. Take the bus or train downtown. Easy walk to wine & dine in posh areas of Roscoe Village, Lake view & Lincoln Square. Or a quick drive to downtown! This is A FULL UPPER FLOOR, and NOT a Garden Basement. You are a short walk away from restaurants, stores but stay in a quiet beautifully appointed 1100 square feet elegant 1 large Bedroom flat with parking all to yourself. Enjoy this -its hard to find in this city. Refurbished to the highest standards this spacious apartment is located moments from shopping, restaurants and pubs in the heart of cool Roscoe Village Lakeview & Lincoln square neighborhoods of Chicago. Famously eclectic and vibrant, we are the heart of Chicago's best offerings. Boyztown, Buck town, Lincoln park or music at Scubas, Stage 777, Revolution Brewery, and other cool hip spots are a short walk or ride away. Home of the CUBS -Chicago’s best attractions "Walking to Wrigley field with all of the other "fans" singing GO CUBS was a fab experience" a guest's comment. The most difficult decision of the day might well be whether to eat out - many restaurants, pubs and bars in the area catering for all tastes and pockets; or to stay in and cook - cozy comfort of a first class home. We are keen for you to enjoy your stay with us, and we will do our best to make your stay a memorable one. The accommodation is the whole upper floor, (one short flight of stairs) and you have your own entrance. Enjoy a luxurious home away from home. You have an entire floor to yourself with 100% privacy. Interaction with our guest is as much or as little as you need, when we are in town. We often travel, but always have a caretaker who will be responsible to ensure satisfaction for your complete stay. Part of the area's charm is not only the elegant vintage Chicago style homes, or how easy it is to walk to all the local favorite dining, but how much personality all the small independent businesses on Roscoe street have. This gives the neighborhood a hip vibe and friendly, small-town feel! Centrally located in the middle of Wrigleville, Lakeview, Bucktown, Logan Square, Lincoln Square and 10 minutes to train station - 5 minutes to bus or divvy bikes. Or park your car FREE - a luxury in Chicago Centrally located, yet quiet and charming you will be within minutes of everything this mega city has to offer. Chicago is a major city second only to New York, in the United States, and is a global alpha city with fantastic offerings. This glittering city built on the shores of Lake Michigan is where you’ll find some of the biggest and best entertainment outside of New York City and Las Vegas, including touring Broadway shows, professional sports teams, stand-up comedy and concert venues – including the iconic Chicago Theater and Grant Park, home of Lollapalooza. The second city is also home to year-round attractions and world-class museums – the Field Museum, the Skydeck at the Willis Tower, Shedd Aquarium, and the Art Institute of Chicago. Chicago sports fans fuel their passion year-round as they cheer on the north side Cubs or south side White Sox in the summer, Bulls and Blackhawks in the winter, and Bears in the fall.

Top guest favourite
The living area features an ornate red damask wallpaper that creates an engaging backdrop. A plush cream-colored sofa is arranged alongside two black armchairs, complementing a glass coffee table atop a vibrant red carpet. Natural light filters through sheer curtains, enhancing the vintage decor.
Apartment in Ukrainian Village
4.91 out of 5 average rating, 87 reviews

Retro lovers dream in the heart of West Town

Immerse yourself in the unique charm of the 1970s with our time capsule Airbnb, where vintage elegance and mobster lore blend seamlessly. This apartment, once inhabited by reputed mobster Joey ‘The Clown’ Lombardo, is a perfectly preserved piece of history, offering guests a rare glimpse into the vibrant 1970s lifestyle, with authentic fixtures, Joey's personal effects, furnishings imported from Italy, and a story that captures the intrigue of a bygone era. Thoughtfully restored to its original splendor, the space provides all modern amenities, including high-end mattresses, central heating, and air conditioning, ensuring a comfortable stay. FEATURES: - Authentic, original vintage decor throughout - New luxury bedding - Wifi; USB charging ports - Central heat and a/c - Hair dryer, cedar closet, and luggage racks - Central location convenient to downtown, west loop, and United Center / UIC **No parties / large groups. Strictly enforced**

Guest favourite
The open living area features a spacious sectional sofa with soft green upholstery, complemented by a round coffee table. Large windows provide natural light, showcasing views of the surrounding cityscape. The modern kitchen, visible in the background, includes stainless steel appliances and bar seating.
Apartment in The Loop
4.93 out of 5 average rating, 74 reviews

Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool

Feel at Home, Unwind, and Enjoy the amenities you deserve at our 3bed 2-Story Penthouse. Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅Central location near Grant Park, Soldier Field, Art Institute& Museums! ✅1 Free parking pass ✅FAST WIFI ✅En-suite Laundry ✅The Lake & Park are 2 blocks away ✅2 KING beds + 1 Queen bed ✅Private Rooftop Deck w/ stunning views ✅Amenity Floor (Gym, Pool, Lounge, Doggy Park) ✅1 block from Red "L" subway

Superhost
A spacious living area showcases a modern kitchen with wooden cabinetry and stainless-steel appliances. A dining table with black chairs is situated next to a cozy seating area featuring a large couch and ample natural light from the windows.
Apartment in Bridgeport
4.8 out of 5 average rating, 187 reviews

Elegant 3/BR w/Balcony by Downtown, Chinatown

Newly developed condo with 3 spacious bedrooms and 2 full baths. Brand new appliances and spacious living room and kitchen. Environment is warm, comforting and modern. Public transportation just steps away. Orange line takes you directly to Midway airport. Buses will take you to major event locations such as McCormick, US Cellular & Soldier Field. Chinatown is just blocks away w/ day and night food & entertainment. Eateries are on the 1st floor for a quick bite. Private, designated parking.

A spacious living area is presented, featuring a comfortable gray sofa and stylish armchair. Large windows allow natural light to fill the room, showcasing views of Chicago's skyline. A dining table is set nearby, complemented by modern decor and a cozy atmosphere.
Apartment in Downtown Chicago
4.67 out of 5 average rating, 12 reviews

Level ◆ Two Bedroom Jr Deluxe + Balcony | Old Town

You won’t need to trade luxury for location when staying with Level in Chicago’s historic Old Town neighborhood, your suite is the whole package with all the comforts of home and thoroughly cleaned to the highest standards. A separate fee totaling $22.32 per night will be added upon arrival. This fee is separate from Airbnb and will be collected at check in. This would include a pet fee of $20 per night per pet as well as a parking charge of 68.30 per night should you choose to utilize.

Guest favourite
A modern living area features large windows that provide ample natural light and views of the cityscape. Two armchairs in contrasting colors flank a glass coffee table, while a stylish sofa offers comfortable seating. A wall-mounted television adds to the entertainment options.
Apartment in Lincoln Park
4.94 out of 5 average rating, 17 reviews

City Views from Large 4th Floor Apartment in LP

A refreshing, sophisticated oasis with added flare like vibrant, oversized works of Chicago memorabilia. Ideal for a family or group of friends, this suite offers a large Queen Bedroom & beautiful full bathroom. A brand new oversized stocked kitchen is on hand to cook a meal (or simply request a chef, you’re on vacay after all) and serene a bathroom complete with luxury bath products feels like home. A washer + dryer, Sonos, YouTubeTV, and fast Wi-Fi add to the ease and comfort.

A modern kitchen features sleek navy cabinetry with gold hardware and a spacious white countertop. Stainless steel appliances are integrated, including a dishwasher. A decorative vase with white flowers adds a touch of elegance, while a geometric rug complements the overall design.
Apartment in West Side
4.65 out of 5 average rating, 20 reviews

Modern Home ~20 min from Downtown

This stylish place to stay is perfect for group trips. Nestled in a prime location, this stunning modern home offers the epitome of convenience and luxury. Boasting three bedrooms and three bathrooms, this residence is a harmonious blend of contemporary design and functionality. Situated near a golf course, tennis courts, and a picturesque fishing lagoon. Step inside, and you'll be greeted by an open-concept layout that seamlessly connects the living, dining, and kitchen areas.

Guest favourite
A modern kitchen features white cabinetry and stainless steel appliances, including a refrigerator and microwave. A marble countertop extends to a bar area with three red stools. Decorative elements, including a vase of flowers, enhance the inviting atmosphere.
Apartment in South Side
4.89 out of 5 average rating, 81 reviews

Washington Estate minutes from University of CHI

Kick back and relax in this calm, stylish space. The Washington Estate is the professional escape. We provide a 1-bed/2-bath to accommodate a maximum of two guests. Everything you need, full kitchen, WIFI, exercise room, in unit laundry and exterior patio seating for your enjoyment. Gated parking available upon request. Near the historic Hyde Park, the University of Chicago and 8 minutes away from Lake Shore Drive. Walking distance from public transportation.

Superhost
A modern living area features a light gray sofa facing a large TV on a low stand. A circular coffee table is situated on a black-and-white striped rug. Natural light enters through the multi-pane windows, with curtains softly framing the space.
Apartment in Bridgeport
4.83 out of 5 average rating, 139 reviews

Bright & Cozy 2 Bedroom Apt - 15 Min to downtown!

Welcome to our cozy Chicago apartment in the historic Bridgeport neighborhood. This comfortable 2 bedroom, 1 bath unit is on the first floor of a classic two flat, offering easy access and a relaxing stay. Steps from a bus stop and just a 5 minute drive to the CTA Orange Line, getting downtown and around the city is simple. Close to Pilsen and Chinatown. For safety, four exterior Ring cameras monitor outside areas only. ID required for all primary guests.

Guest favourite
Apartment in Downtown Chicago
4.88 out of 5 average rating, 155 reviews

Guild #1 | Gold Coast Mag Mile Best Location

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - Steps away from the John Hancock - Gym in the Basement - Amazing location w/ many shops & restaurants nearby - Fast WIFI - KING beds - Charming, vintage Chicago building Walk to nearly any attraction in central Chicago. Please read our FAQs to answer any questions before booking.

Superhost
The room features a spacious bed adorned with decorative pillows and a soft blanket. Walls are painted in soothing colors, complemented by elegant curtains and modern furnishings. A cozy chair and a desk are arranged near a large window, allowing natural light to illuminate the space.
Apartment in Wicker Park
4.76 out of 5 average rating, 41 reviews

Hotel Quality Meets Local Living King Room 3C

Quaint, cozy and 100% private, our overnight Guest Rooms offer honest to goodness pillow top mattresses with 500 thread count linens. Comfortable, simple and clean, additional features include: Private glass and marble showers, comfy chair, desk, custom woodworking and molding abound. Carpeted floors, oriental rug, natural light, modern and vintage décor/furnishings, high speed internet access, soft comforters and thirsty towels.

Superhost
A modern living area features a spacious sectional sofa paired with a green accent chair. A large dining table, surrounded by white chairs, sits under an elegant light fixture. Windows allow natural light, complementing the sleek design of the open-plan layout.
Apartment in Lincoln Park
4.81 out of 5 average rating, 67 reviews

Lincoln Park Coach House w Kitchen & Queen Sleeper

Stylish East Lincoln Park Coach House. Large one bedroom unit with queen bed + queen sleeper sofa in the living room. This apartment features a spacious living room with a dining table for 8- great space for a dinner with friends or for a work-from-home setup! Plenty of room for a family.

Popular amenities for The Loop serviced apartments

When is the best time to visit The Loop?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$210 CAD$208 CAD$231 CAD$275 CAD$270 CAD$339 CAD$332 CAD$314 CAD$281 CAD$307 CAD$277 CAD$233 CAD
Avg. temp-3 °C-1 °C4 °C10 °C16 °C22 °C25 °C24 °C20 °C13 °C6 °C0 °C

Quick stats about serviced apartment rentals in The Loop

  • Total vacation rentals

    Explore 60 vacation rentals in The Loop

  • Nightly prices starting at

    The Loop vacation rentals start at $83 CAD per night before taxes and fees

  • Verified guest reviews

    Over 360 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    60 of The Loop vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across The Loop rentals

  • 4.8 Average rating

    The Loop stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    The Loop’s top spots, include Millennium Park, Shedd Aquarium, and Willis Tower

Destinations to explore