Apartment holiday rentals in Chicago

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Chicago

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

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Guest favourite
A modern living area features two stylish seating options, one bright green sofa and a deep blue accent chair with matching ottoman. Natural light filters through large windows adorned with horizontal blinds, highlighting the light wood flooring and contemporary decor.
Apartment in Little Village
4.88 out of 5 average rating, 437 reviews

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen

Brand New Private Modern 2 bd 2bth apt for your stay in Chicago. We are located 2 blocks form the CTA line in the heart of Pilsen, a neighborhood Time Out labeled the 10th coolest in the world. Newly renovated, hardwood tiled floors throughout, chefs kitchen, toiletries, brand new furnishings including 2 queen beds, 1 twin sleeper, fresh linen, smart TV (HBO, Netflix, Hulu) wifi, tons of books,coloring books,board games & puzzles! We truly want you to feel like this is your home away from home.

Top guest favourite
A cozy living space features a vibrant orange sofa complemented by decorative throw pillows. A dining area with a small table stands beside a fully equipped kitchen. Artwork adorns the walls, while natural light streams through windows, enhancing the inviting atmosphere.
Apartment in Lake View
4.97 out of 5 average rating, 117 reviews

Chic & Comfy • Close to Wrigley

Welcome to your comfy, cozy, cheerful hideaway in the beautiful Buena Park!☀️ Buena Park is a little-known gem. Our home is just blocks from the lakefront (4 blocks), Wrigley (6 blocks), and the major L-line in Chicago (1 block)...yet, you'd never know it given how peaceful and serene it is! We live here part-time, so rest assured you'll have everything you need for a comfortable and enjoyable stay. We ask you please respect our place, and that you enjoy the trinkets + personal items we have!

Guest favourite
A spacious living area features a large sectional sofa facing a media unit with a TV, accompanied by a coffee table. A dining table with four chairs sits nearby. Floor-to-ceiling windows provide bright natural light and a view of adjacent buildings.
Apartment in Gold Coast
4.86 out of 5 average rating, 206 reviews

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

Top guest favourite
A spacious rooftop deck features comfortable wooden seating arranged around a circular table. The area is adorned with vibrant flowers and a decorative rug, all set against a sweeping view of the Chicago skyline under a soft blue sky.
Apartment in Wicker Park
4.94 out of 5 average rating, 184 reviews

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Escape into this spacious, Chicago Penthouse! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Private, spacious roof deck viewing the entire Chicago skyline! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out - Designated parking spot! - Steps away from blue line Damen station (800 feet)

Top guest favourite
A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.
Apartment in Little Italy
4.95 out of 5 average rating, 244 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Guest favourite
An outdoor patio is showcased, featuring a rectangular fire table surrounded by four cushioned chairs. The wooden decking contrasts with the subdued colors of the furniture. A partial cover is draped over one corner, providing shade from the sun.
Apartment in West Town
4.96 out of 5 average rating, 166 reviews

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Explore Chicago's charm just moments from downtown! This Airbnb boasts a spa bath with a luxurious rain shower and jetted tub, a fully equipped kitchen for culinary adventures, comfortable reclining sofas for relaxation, and ample space to unwind. Sleep like royalty in the master bedroom's king bed, and a queen murphy bed in the living area ensures a comfortable stay for up to four guests. Step outside to the patio with a fire pit for cozy evenings. Your Windy City getaway begins here!

Top guest favourite
A spacious living area showcases a light-colored sectional sofa paired with two vibrant blue accent chairs. A round glass coffee table sits at the center, complemented by a light rug. The open kitchen features dark cabinetry and modern appliances, enhancing the contemporary design.
Apartment in Chicago
4.83 out of 5 average rating, 174 reviews

Rogers Park Stay Near Loyola, Transit w/ Parking

Our 3 bedroom and 2 bathroom condo has a perfect open layout for any size group that is traveling together. You'll have a ton of open space to share and feel at home, while also choosing from 3 bedrooms to get some privacy as well. Each bedroom has a queen size bed, while the master bedroom also has its own full size private bathroom. Feel free to stay in and cook with our fully equipped kitchen, enjoy the 65 inch Roku TV, and gather around the very large island.

Top guest favourite
A spacious living area is filled with natural light from multiple windows. A comfortable sofa, adorned with a decorative pillow, is positioned in the corner. A dining table and chair are visible in the background, with greenery seen through the windows.
Apartment in North Side
4.97 out of 5 average rating, 189 reviews

Lincoln Park 2bed/2bath in Historic Neighborhood

Just steps from the lively center of Chicago's Lincoln Park and poised above the quiet, tree-lined streets of the coveted Arlington-Deming neighborhood, this residence on the top floor of a three-story walkup is the perfect for families that want to be close to it all! Lake Michigan, Lincoln Park Zoo, multiple parks, transportation, dining, nightlife, and more. We provide one daily parking permit per night of your stay so you can access free street parking.

Superhost
Apartment in Grant Park
4.82 out of 5 average rating, 149 reviews

Cozy Downtown MICH AVE #7 | gym+rooftop

Feel at Home and Unwind when you come to Chicago. Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Queen beds -1 closed & 1 loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you're interested in booking, see our FAQs below.

Superhost
A modern living area features a large black leather couch accompanied by a sleek armchair. Artistic Chicago-themed decor adorns the walls, including a vibrant sign. Natural light fills the space through window coverings, with a stylish area rug enhancing the warm ambiance.
Apartment in Ukrainian Village
4.9 out of 5 average rating, 177 reviews

Modern Chicago Movie Themed Apt

Welcome to Chicago at the Movies! An amazing fully updated apartment in the Ukrainian Village neighborhood. This midcentury modern 3 bedroom home is perfect for groups, couples, and families looking for a perfect Chicago vacation. The property is conveniently located on Grand Avenue just minutes by car, bus or train from Downtown and the Lakefront. We are also just a short 5 Minute ride to the United Center for concerts sports and more!

Top guest favourite
An open kitchen and dining area features exposed wooden beams and stylish light fixtures. A modern dining table with black chairs provides seating, while a lounge chair is positioned nearby. Decorative plants and art add warmth to the contemporary space.
Apartment in Wicker Park
4.95 out of 5 average rating, 131 reviews

Modern Izakaya Studio in Wicker Park

Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

Top guest favourite
The bright living area features a blue sofa with decorative pillows, a wooden coffee table, and a desk chair facing a small workspace. Natural light enters through multiple windows, showcasing the hardwood flooring and modern decor elements, including a framed cityscape artwork.
Apartment in Lake View
4.99 out of 5 average rating, 669 reviews

Urban Comfort in the Heart of Chicago

This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and a newly remodeled en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.

Popular amenities for Chicago apartment rentals

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Quick stats about apartment rentals in Chicago

  • Total holiday rentals

    Explore 1,020 holiday rentals in Chicago

  • Nightly prices starting at

    Chicago holiday rentals start at € 17 per night before taxes and fees

  • Verified guest reviews

    Over 71,130 verified reviews to help you choose

  • Family-friendly holiday rentals

    610 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 300 rentals that welcome pets

  • Holiday rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    660 properties have a dedicated workspace

  • Wifi availability

    1,000 of Chicago holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chicago rentals

  • 4.8 Average rating

    Chicago stays are highly rated by guests – averaging 4.8 out of 5!

  • Nearby attractions

    Chicago’s top spots include Millennium Park, Wrigley Field and Lincoln Park

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