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.

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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.

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, 85 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**

Top guest favourite
Apartment in Lincoln Park
4.96 out of 5 average rating, 148 reviews

English garden apt. in the heart of Lincoln Park

Welcome to this new, totally furnished apartment in the heart of East Lincoln Park…only a 3 minute walk to the Lincoln Park Zoo! Apartment has been completely renovated with high finishes throughout. Living room boasts a 50” television with Dish TV, internet and a queen sleeper sofa! Gourmet kitchen with granite counter tops with an eat-in bar height counter top. Truly gourmet kitchen! Bedroom with en-suite European styled bathroom. Wall mounted television in the bedroom. In unit laundry.

Apartment in Chicago
4.85 out of 5 average rating, 33 reviews

“The Marlowe” A Couples Getaway

Couples Getaway: Your Ultimate Lovers Nest Welcome to Couples Getaway, an enchanting one-bedroom retreat designed for romance and relaxation. Nestled in a serene setting, this cozy haven features a luxurious six-person hot tub, perfect for unwinding under the stars. Inside, indulge in cinematic experiences with an 80-inch smart TV, equipped with all the latest movies, channels, and series. The living room boasts surround sound, allowing you to create the perfect ambiance for a cozy night in.

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.

Apartment in Lincoln Park
4.69 out of 5 average rating, 99 reviews

Apartment in Lincoln Park, second bedroom optional

Great Central Location, steps away from the corner of Clark and Wrightwood. Second bedroom w/ twin size bed available for an extra fee. Default reservation is for bedroom w/queen size bed. Inquire for availability and pricing for second bedroom. We offer weekly, bi-weekly and monthly discounts. As well as weekdays. Discount applied automatically at time of reservation. Meet in person to check in. Let host know time of arrival. Early or late check-in available for a fee. Street parking.

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, 80 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
The exterior of a two-flat building is shown, featuring a brick facade with a contrasting blue section. A set of black iron stairs leads to a door on the upper level. Surrounding areas include landscaped grounds and black railings along the pathway.
Apartment in Bridgeport
4.84 out of 5 average rating, 138 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.

Superhost
A rooftop deck features a spacious layout with lounge chairs and tables, surrounded by greenery. Grilling stations are positioned on the side. The area is bathed in natural light, with views of the surrounding buildings against a clear blue sky.
Apartment in The Loop
4.84 out of 5 average rating, 100 reviews

MICH AVE Downtown, Park, Museums 2bd #4

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: ✅ Central location close to Museum Campus ✅ Parking Garage attached to the building ($15-30 / night) ✅ FAST WIFI ✅ Big, Comfy KING beds ✅ Rooftop Deck ✅ 1 block from the Red, Orange, Green L subway stops ✅ Close proximity to Grant Park, Soldier Field, Museums & more!

Superhost
An outdoor heated pool is surrounded by modern lounge chairs and cabanas. The pool area is framed by sleek building facades, while tall skyscrapers and clear blue skies provide a vibrant backdrop, emphasizing the inviting space for relaxation.
Apartment in Downtown Chicago
4.8 out of 5 average rating, 70 reviews

Level ◆ Brand New Luxe Studio

With 542 sq ft of modern, functional accommodations, our Level Suites feature a spacious studio layout with fully-equipped kitchen, open-concept living room with sofa bed, comfortable sleeping space, spa-inspired bathroom and ample closet space. Designed for comfort and convenience, all suites boast in-suite laundry, premium appliances, flat-screen TV with cable, complimentary WiFi and local calling. Space to live and play? That’s pretty suite.

Superhost
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.

Guest favourite
Apartment in Downtown Chicago
4.89 out of 5 average rating, 18 reviews

Level ◆ Studio Apartment

With 560 - 630 sq ft of modern, functional accommodations, our Level Suites feature a spacious studio layout with fully-equipped kitchen, open-concept living room and sleeping space, plus spa-inspired bathroom. Designed for comfort and convenience, all suites boast in-suite laundry, premium appliances, flat-screen TV, complimentary WiFi and local calling. Space to live and play? That’s pretty suite.

Popular amenities for The Loop serviced apartments

When is the best time to visit The Loop?

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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