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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Top guest favourite
The living area showcases a spacious layout, featuring a comfortable couch, a modern glass coffee table, and a stylish armchair. Natural light floods the room through large windows, accentuated by hardwood flooring and a decorative rug. A dining table for four is positioned nearby, along with a colorful wall art.
Apartment in Wicker Park
4.92 out of 5 average rating, 137 reviews

WONDERFUL WICKER PARK 2BD/2BA w/ patios +parking

Escape into this spacious condo in a bustling top-notch, Chicago neighborhood! 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! - 2 private walk-out patios! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out patio - Designated parking spot! - Steps away from blue line Damen station (800 feet)

Guest favourite
The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.
Apartment in Avondale
4.96 out of 5 average rating, 140 reviews

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE with garage parking! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Guest favourite
A cozy living area features exposed brick walls, a rustic wooden coffee table, and a large leather sofa. A flat-screen television is positioned in front of the seating, while natural light enters through the windows. A vintage fan rests nearby, and additional storage is provided by a bookshelf.
Apartment in Humboldt Park
4.86 out of 5 average rating, 492 reviews

Humboldt Park Traveler's Lodge

Come stay at my gorgeous condo! Featuring exposed brick, a private entrance, stainless steel appliances, and a queen bed --> all on a quiet tree lined street! It's a perfect place to re-energize between big city adventures. Free street parking, and a 5 min walk to some of the best independently owned shops, restaurants, and bars in the city. Also, the massive and incredible Humboldt Park is also just a 5 min walk away! Please reach out for recommendations - I love giving them to people!

Top guest favourite
A modern kitchen features green cabinetry and a marble-topped dining table surrounded by two chairs with woven seats. A geometric backsplash adds visual interest, while cookware and decorative elements are thoughtfully arranged on the shelves above. Natural light illuminates the space.
Apartment in North Center
4.98 out of 5 average rating, 105 reviews

Grace House | Cozy, contemporary + convenient 2-BR

Make yourself at home in our newly renovated, spacious and immaculately clean 2-bedroom, 1-bath condo — perfect for your next family, work or friends' trip. Located on a tree-lined street in a family-friendly neighborhood and walkable to shops, restaurants, cafes, bars and more. A stone's throw to Southport Corridor/Wrigleyville/Lakeview, Lincoln Square, Roscoe Village and everything the Northside has to offer. Gigabit internet w/ WiFi and everything you need to live and thrive in Chicago.

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
4.94 out of 5 average rating, 249 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!

Guest favourite
A bright living area is illustrated with large windows allowing natural light to fill the space. A comfortable beige sectional sofa provides seating, while a wooden coffee table sits on an area rug. A desk with modern design and a chair are present, enhancing the workspace.
Apartment in Humboldt Park
4.93 out of 5 average rating, 149 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

Experience a calm and soothing stay in a space bathed with light and nestled amongst the trees. This top floor unit in a 3-flat condominium building offers you the serenity of a neighborhood with tree lined streets, and the convenience of being 3 miles from the heart of downtown Chicago. As a bonus, you're a 2min walk from public transportation. For something closer to home, Wicker Park and Humboldt Park offer great dining and culture steps away. We look forward to hosting you!

Top guest favourite
The living area features exposed brick walls and hardwood floors, with an arrangement of seating including a red armchair and a cozy sofa. A glass coffee table sits on a plush area rug. A wall-mounted flat-screen TV is present, alongside indoor plants and decorative elements.
Apartment in Lincoln Park
4.99 out of 5 average rating, 314 reviews

of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

• 1,750ft² / 162m² . My home is on the second floor of a four flat Itallian Brick Building . You have 2 flight of stairs to Climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport fireplace is not operational.

Top guest favourite
A modern living area features a green sofa positioned in front of a glass coffee table on a patterned rug. An open kitchen with white cabinetry and stainless steel appliances is visible in the background. Natural light fills the space, enhancing its welcoming atmosphere.
Apartment in Uptown
4.97 out of 5 average rating, 152 reviews

Large 2BR, 2BA, patio, sunroom, W/D, L-kitchen

Welcome to our charming home in the peaceful yet centrally located Buena Park neighborhood, housed in an updated antique building. This prime location offers easy access to the Red and Purple train lines, as well as multiple bus routes, making it easy to explore Chicago. You’ll be within walking distance of Wrigley Field, Clark St. bars, Montrose Beach, Lakeview, Boystown, and the iconic Green Mill. A perfect blend of quiet comfort and proximity to Chicago’s best attractions.

Guest favourite
A modern living area features a dark sofa adorned with colorful throw pillows. A wooden coffee table rests in front, and light streams in through large windows that offer views of the surrounding city. A dining table with chairs is visible in the background.
Apartment in Grant Park
4.89 out of 5 average rating, 152 reviews

Downtown Park #11 - Mich Ave PH | gym+rooftop

Feel at Home, Unwind, and Enjoy the amenities you deserve 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 bed -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 are looking for a special place, you've found it!

Guest favourite
A modern kitchen with white cabinetry features stainless steel appliances, including a refrigerator and microwave. An island with seating for three is complemented by decorative vases of flowers. Natural light fills the space through large east-facing windows.
Apartment in Gold Coast
4.9 out of 5 average rating, 172 reviews

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

Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

Superhost
This studio apartment features a modern kitchen with wood cabinetry and black appliances. A small dining table with curved blue chairs and a vibrant orange sofa create an inviting living space. Natural light enters through large windows, illuminating the minimalist decor.
Apartment in River West
4.79 out of 5 average rating, 174 reviews

Cabin 207 at 747 Lofts

This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away!

Popular amenities for Chicago apartment rentals

When is the best time to visit Chicago?

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Avg. price$155 SGD$155 SGD$179 SGD$189 SGD$217 SGD$229 SGD$231 SGD$238 SGD$210 SGD$202 SGD$193 SGD$182 SGD
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Quick stats about apartment rentals in Chicago

  • Total holiday rentals

    Explore 1,000 holiday rentals in Chicago

  • Nightly prices starting at

    Chicago holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 72,870 verified reviews to help you choose

  • Family-friendly holiday rentals

    600 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 280 rentals that welcome pets

  • Holiday rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    650 properties have a dedicated workspace

  • Wifi availability

    990 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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