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Holiday rentals with beach access in Chicago

Find and book unique accommodation with beach access on Airbnb

Quick stats about holiday rentals with beach access in Chicago

  • Total holiday rentals

    Explore 490 holiday rentals in Chicago

  • Nightly prices starting at

    Chicago holiday rentals start at $52 NZD per night before taxes and fees

  • Verified guest reviews

    Over 32,550 verified reviews to help you choose

  • Family-friendly holiday rentals

    280 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 160 rentals that welcome pets

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    410 properties have a dedicated workspace

  • Wi-Fi availability

    490 of Chicago holiday rentals include Wi-Fi 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

Top-rated Accommodation with Beach Access in Chicago

Guests agree: These holiday homes with beach access are highly rated for location, cleanliness and more.

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Top Guest favourite
The master bedroom features a spacious bed with a tufted headboard and soft, neutral bedding. Two nightstands with lamps are on either side, and a television is mounted on the wall. Natural light filters through the wooden blinds, enhancing the warm wooden floors.
Apartment in Downtown Chicago
4.94 out of 5 average rating, 251 reviews

OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)

Welcome to this Old Town Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Wells St. - Close to every popular attraction that makes Chicago so great - Room for reg-size SUV in private driveway! - Luxurious interior design - Tranquil rooftop w/ grill - Fast WiFi - Pillow-top Bamboo mattress in each master en-suite - State of the art kitchen - Exceptional workspace - 5 minute walk from red line (CTA L) We look forward to hosting you!

Guest favourite
A vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.
Apartment in South Side
4.9 out of 5 average rating, 172 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TV, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles), Navy Pier, Obama Library, Millennium Park, Beach (1 mile), Museum, & Sports arenas.

Top Guest favourite
An outdoor terrace features comfortable lounge seating and a grill. A panoramic view of the Chicago skyline is visible, showcasing various architectural styles and buildings under a clear blue sky.
Townhouse in West Loop
4.99 out of 5 average rating, 283 reviews

HUGE 4BR Townhouse FultonMarket/WestLoop!

Stay in a spacious 4-story townhouse in Chicago's vibrant West Loop/Fulton Market, just steps from Restaurant Row, award-winning restaurants, nightlife, coffee shops, parks, and grocery stores. Enjoy the excitement of the neighborhood while staying on a quiet, treelined street for a peaceful night's sleep.Features include a private rooftop terrace with skyline views, an attached garage (1 regular vehicle fits), and easy access to public transit for O'Hare, downtown, Navy Pier, Mag Mile and more.

Top Guest favourite
A red brick three-flat building is presented with large windows and intricate architectural details. Colorful pumpkins are arranged in the front garden, which features lush greenery and blooming flowers. A rainbow flag is displayed prominently by the entrance, adding a touch of vibrant color.
Apartment in Andersonville
4.99 out of 5 average rating, 140 reviews

Andersonville 2 bed with modern kitchen + bath

Hi, we're Mike and Lora. Our beautiful Mission-style three-flat is located about 100 ft. from Clark St. in Andersonville, with great bars, restaurants, and shopping just outside our door. Half a mile east is the Red Line, which gets you right downtown, and just past that is beautiful Foster Beach. We live upstairs and are happy to offer recommendations. We love it here! The apartment was rehabbed in 2019 and features a large kitchen with tons of counter space, in-unit laundry, and queen beds.

Top Guest favourite
A living area features natural light from multiple windows, complemented by a ceiling fan. A comfortable sofa with textured throws faces a modern fireplace. Two brown armchairs are positioned nearby, and a decorative rug lies under a coffee table, which displays a potted plant and a magazine.
Apartment in Evanston
4.99 out of 5 average rating, 113 reviews

Evanston 2BR 2Bth 1 Blk to Beach

With its older charm, modern comforts, and unbeatable proximity to the beach, this 2-bedroom, 2-bath unit offers an ideal getaway. Only 1 block from beautiful Lake Michigan and South Blvd Beach, you will love our spacious, sunny apt. Whether you're staying for a short visit or a lengthy one, you'll feel the comfort of home on a tree-lined street. The unit has hardwood floors throughout, comfortable bedrooms, a fully stocked kitchen, dining room, and a sunroom looking out on the backyard patio.

Guest favourite
A serene garden space is presented, featuring green grass and a variety of plants and trees. Two light-colored Adirondack chairs are positioned on the lawn, surrounded by vibrant foliage. The backdrop includes brick buildings and a pathway, creating a welcoming outdoor environment.
Apartment in West Town
4.8 out of 5 average rating, 230 reviews

Wicker Park Historic, Art-Filled, Urban Oasis #2

Entire 2 bedroom apartment in art filled,wicker park building 5 min from downtown Chicago. Quick walk to shops,restaurants,public transportation,parks,night life,etc. Space includes -Nice bathroom,walk in shower -1 bdrm w/ queen size bed,tv,desk,large closet -1 bdrm w/ single bed & closet -1 sleeper couch w/ full size pullout bed & mattress pad -1 foldable twin bed -1 queen size blow up air mattress -Fully equipped kitchen -Beautiful garden -1 parking space included + parking passes available

Top Guest favourite
A modern kitchen features sleek gray cabinetry and stainless steel appliances, including a refrigerator and oven. A neutral area rug complements the wood flooring. Natural light is provided by large windows, and stylish wall decor adds a contemporary touch to the space.
Condo in Lake View
4.98 out of 5 average rating, 262 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $20/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

Top Guest favourite
A private patio provides a cozy seating area featuring a 3-seater sofa and two accent chairs. A round coffee table sits in the center, with the urban street view visible beyond the wrought iron railing.
Apartment in Downtown Chicago
4.95 out of 5 average rating, 120 reviews

Gold Coast Pristine 3BD|2BR| Patio |Parking| Beach

FREE GARAGE PARKING! Garage Clearance 6ft. Step into luxury in this modern loft with 3 bedrooms, 2 bathrooms and a private patio with breathtaking views. Experience the feeling of being at home in a bright and spacious haven amidst Chicago's most sought-after neighborhood "Gold Coast" This centrally located gem is situated within walking distance of much of Chicago Downtown's exquisite dining, upscale boutiques, popular tourist destinations, and just a stone throw away from Oak Beach.

Top Guest favourite
An open living area features a modern kitchen with stainless steel appliances and granite countertops. A dining table with seating for four is positioned next to a cozy seating area, which includes a large sofa and wall-mounted TV. Natural light filters through the windows.
Apartment in Downtown Chicago
4.96 out of 5 average rating, 105 reviews

Old Town Tranquility (+parking)

Relax and unwind at this one-of-a-kind getaway! Guests love this space because: - Steps away from top-notch restaurants/entertainment on bustling Wells St. - Close to every popular attraction that makes Chicago so great - Privacy is hard to beat in this beautiful courtyard! - Extremely Fast WiFi - Pillow-top Bamboo mattress and SMART TV in lofted bedroom - Exceptional workspace - 5-10 minute (0.4 mile) walk from Clark/Division red line station (CTA L) We look forward to hosting you!

Top Guest favourite
A spacious living area is furnished with two leather sofas, a coffee table, and a decorative rug. A television is mounted above a tiled fireplace, and large windows allow natural light to fill the room. A comfortable armchair is positioned near the window.
Apartment in Lake View
4.99 out of 5 average rating, 156 reviews

Spacious 2 Bedroom in the heart of Lakeview!

Come enjoy this warm and spacious 2br/1ba vintage apartment in the heart of Lakeview! 10 Minute walk to Wrigley Field and steps away from many dining and shopping options. Fully stocked kitchen, dining room (seats six), decorative fireplace, TV w/ Fire Stick, two bedrooms with queen beds, office space for working remote, and large private deck with gas grill. Very close to Lake Shore Drive, short walk to the Belmont L, and easy access to many buses. Two night minimum stay.

Guest favourite
A cozy living room area features a dark leather sofa facing a mounted television on a wooden media console. A round shelf displays books and plants, while a small desk and chair are positioned beside a bright window.
Apartment in Bridgeport
4.93 out of 5 average rating, 239 reviews

Blue Brick Apartment in Bridgeport - Park for Free

• Free street parking • Trains to Downtown!! • Fully stocked kitchen • Walk to dining & bars! • Free parking pad in rear • Noise monitoring equipment • Walk score 93! Bike Score 92! • 600 sq ft apartment | 2nd floor | Patio • Safe, working class neighborhood! • Commute to Downtown: 15min (drive) • 28min (transit/train) | 22min(bike) • Building video surveillance alarm system • Washer | Dryer | Dishwasher are included • Rideshare (Uber/Lyft) | Bikeshares(Divvy)

Guest favourite
Apartment in Downtown Chicago
4.98 out of 5 average rating, 212 reviews

Elegant Suite in Gold Coast

Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, this generous one-bedroom apartment is perfectly situated in the middle of the action for your Chicago adventure. ***Please note that from March until the end of September 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***

Popular amenities for Chicago Accommodation with Beach Access

When is the best time to visit Chicago?

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Avg. price$242 NZD$237 NZD$266 NZD$266 NZD$318 NZD$328 NZD$330 NZD$337 NZD$306 NZD$299 NZD$273 NZD$264 NZD
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Destinations to explore