Holiday rentals with beach access in Chicago

4.9 out of 5 average rating, 181 reviews

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

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.

WalkabilityConditionKitchen

A modern living area features a spacious orange sofa and a wooden coffee table positioned on a light rug. A large flat-screen television is mounted on the wall, with a stylish lamp and potted plant nearby. An open kitchen with white cabinetry and stainless-steel appliances is visible in the background.

4.97 out of 5 average rating, 156 reviews

Bright & Modern Apt | Steps to Lake, Train, Food

This is the ideal location for your trip to Chicago! Steps from the Red Line Train, Foster Beach, Lake Shore Drive, Lake Front Trail, amazing Restaurants & a quality grocery store. You'll enjoy a clean & spacious 2 bedrooms apartment w/ friendly neighbors, flawless check-in & reserved parking. This place is safe & provides a beautiful & stocked apartment to relax after a busy day in the city. Short walk to Andersonville & Asia on Argyle for wonderful food options. The Riv &Aragon for concerts

WalkabilityBeachLong stay

4.83 out of 5 average rating, 329 reviews

A lush garden area is visible, featuring a green lawn surrounded by various plants and trees. A hammock hangs between two supports, providing a comfortable resting spot. Sunlight filters through the foliage, illuminating the outdoor furniture and creating a peaceful atmosphere.

Apartment in West Town

Wicker Park Historic, Art-Filled, Urban Oasis #1

Entire 2 bedroom apartment in art-filled, Wicker Park building 5 min. Uber to downtown Chicago. Public transportation 3 blocks away. Restaurants, shops, parks, and nightlife within walking distance. Space includes -Brand new bathroom, walk in shower -1 bdrm w/ queen size bed - large closet -1 bdrm w/ single size bed, desk, shelf space -Pull out queen size couch bed -Fully equipped kitchen -AC -Personal back porch -Beautiful garden w/ outdoor furniture -1 parking space included + parking passes

ViewWalkabilityCondition

4.92 out of 5 average rating, 290 reviews

The historic stone façade of the building features intricate architectural details, with large arched windows and a welcoming entrance. Flower pots are displayed on the balcony, and a wrought iron fence surrounds the property, adding to the charm of the exterior.

Apartment in Lake View

Stone Mansion Sleeps 10-20 Free parking & TV

Giant, 4 bedroom, 2,300 square feet apartment on 2nd floor, near Red Line Train, bars, cafe's, shopping, restaurants, Lakefront and everything else Chicago has to offer. Large living room with bar area, TV and fridge for socializing before hitting the town. Dining room has a large table and 8 chairs. 4 bedrooms with 2 private rooms with king beds and one with a double bed. 4 futons for in the living room for extra sleeping space two (2) parking spots in the west facing garage on premises.

BeachWalkabilityAccess

Guest suite in Andersonville

The living area features a comfortable blue sofa adorned with decorative cushions, complemented by a patterned rug. A soft pink armchair and a small round coffee table are present. A vibrant floral painting hangs on the wall, and natural light enters through the window covered by light curtains.

Gorgeous, cozy 1-bedroom Suite in Andersonville

Our place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, location, complete privacy and NO cleaning fee. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.

ViewBeachKitchen

4.96 out of 5 average rating, 417 reviews

4.95 out of 5 average rating, 105 reviews

An outdoor patio area is shown with a glass table and two metal chairs. Potted plants and flowers add greenery along the edges. A brick wall provides a rustic backdrop, while a staircase is visible in the background, leading to the upper level.

Home in Lincoln Park

Cheryl's on Sheffield! 3 bedroom in Lincoln Park.

Bring the whole family to this great place with lots of room for fun. Lots of natural sun light. Starbucks at the corner, along with many other food options. The train is only a block away and will take you directly to Wrigley Field! Free street parking! The Zoo is 1.5 miles directly East and the incredible museums that Chicago has to offer is either a 15 minute train ride or Uber ride away. You will not be disappointed with this location. It has everything you can ask for. It's magical!

ViewWalkabilityFamily

Townhouse in Lincoln Park

Hidden Gem - 3 Story House & Pet Friendly!

Cozy & entertaining family -pet friendly property in the heart of Chicago - Lincoln Park. This Smart triplex has a fully-equipped kitchen. Large patio w/ sunset views. 3 bedrooms & 2.5 bathrooms. A Foosball table, 82' TV & BAR to enjoy a night in. This property is perfect to book w/ family or friends. Its spacious yet set up the right way to entertain in one floor, cook in another & sleep without having to deal with noise. Pets: Certain restrictions may apply. It is $35/night per pet

WalkabilityAir conditioningBathroom

4.95 out of 5 average rating, 128 reviews

Apartment in Downtown Chicago

A well-appointed bedroom features a spacious bed with layered linens and decorative pillows. Soft lighting from two bedside lamps complements a small desk and chair positioned near a window. Rich wood tones and a colorful area rug enhance the room's inviting atmosphere.

Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D

Private 2BR apt. in vintage 3-flat in the heart of Chicago's Michigan Ave/Gold Coast neighborhood. Fantastic locations steps from world-class shopping and restaurants, Oak St. beach, and public transportation (L trains, express bus). Includes A/C, washer-dryer, super-fast wi-fi, smart TV, and workspace. Hourly rate garage parking next door. Note: Guests must walk up one flight of stairs. Light sleepers should bring earplugs as there are noises typical of a big city.

BeachWalkabilityFamily

4.95 out of 5 average rating, 304 reviews

4.93 out of 5 average rating, 249 reviews

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

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)

BeachWalkabilityParking

4.87 out of 5 average rating, 211 reviews

A cozy living area features comfortable seating with a dark blue sofa, two armchairs, and a wooden coffee table. Natural light streams through large windows adorned with decorative frames. A small decorative tree and artwork add warmth to the space, complemented by a soft area rug.

Home in Lincoln Park

Historic Old Town, Fabulous 4 Bedroom Home

Lovely Historic 4 Bedroom, 3 bathroom home in Old Town, walking distance of restaurants, boutiques, coffee shops, the lake front and excellent public transportation. 2nd Fl. Master Bedroom has a King size bed and Twin plus private bath with bathtub, walk in shower, w/d; 2nd Fl. two room "suite" with a Queen size bed in each room and private bathroom. 1st Fl. bedroom with Queen bed and private bathroom. Off Street Parking and Private Deck! License Pending.

BeachWalkabilityCheck-in

4.98 out of 5 average rating, 128 reviews

The exterior of a three-unit building features a blend of brick and stone elements, with large windows providing ample natural light. A well-maintained lawn includes shrubs and small trees, complemented by a walkway leading to a blue door beneath a covered entryway.

Apartment in Evanston

3 BR Evanston Apt near Chicago

3 Miles to Northwestern and 2.5 to Loyola Universities. Enjoy local shopping, entertainment & restaurants in Evanston. Walk, bike or drive to Lake Michigan's beautiful beaches. CTA to Chicago nearby. Two BRs with king beds and a third BR with a full. LR has turntable, records, Netflix, Max, Disney+, Hulu... Enjoy a ping pong table and puzzles. Work space in two bedrooms. Kitchen has a stove, oven, microwave, coffee maker, and toaster. Free off-street parking.

ViewWalkabilityAccess

A cozy living room is presented with a soft area rug and a contemporary ceiling fan. Two armchairs in vibrant colors face a stylish sofa adorned with decorative pillows. A coffee table sits in the center, while a large mirror and art piece add visual interest to the space.

4.98 out of 5 average rating, 166 reviews

Stylish 2BR Andersonville — Walk to Lake & Cafés

Steps to Chicago’s lakefront, cozy cafes, and Andersonville’s best shops. This bright 2BR blends vintage charm with fast Wi-Fi, plush bedding, and a fully stocked kitchen—ideal for couples, remote workers, and weekend explorers. Stroll tree-lined streets, explore the nearby lakefront, or curl up indoors as the seasons change. Enjoy Superhost hospitality for an effortless stay. We’d love to host your next Chicago escape.

BeachWalkabilityOutdoor spaces

Popular amenities for Chicago Accommodation with Beach Access

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

A modern living room features a large white leather sectional sofa positioned near a wall-mounted television. A sleek electric fireplace is located beneath the TV. Bright overhead lights illuminate the space, while potted plants and windows add natural accents.

4.95 out of 5 average rating, 167 reviews

Quiet city getaway by beach in fun neighborhood

WalkabilityBeachCheck-in

4.99 out of 5 average rating, 118 reviews

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

Evanston 2BR 2Bth 1 Blk to Beach

WalkabilityViewEV charging

A spacious living area is adorned with floral wallpaper, featuring a comfortable gray sofa and a wooden coffee table. Two white chairs are positioned around a woven rug. An open kitchen area is visible, equipped with modern appliances and green bar stools at the counter.

4.94 out of 5 average rating, 191 reviews

Andersonville's Secret Garden: 2 beds, 1 bath

BeachWalkabilityCondition

Apartment in East Rogers Park

A spacious living area features a large sectional sofa adorned with decorative pillows, positioned opposite a wooden TV stand. Natural light filters through the windows, illuminating the modern decor and a light-colored area rug. A small coffee table and wall art complement the inviting space.

New 2 br/1 bth, free parking, near Lake & Loyola

WalkabilityBeachCleanliness

4.97 out of 5 average rating, 122 reviews

Apartment in Downtown Chicago

The Lakefront Lookout (Rooftop Deck • Gym)

ViewBeachWi-Fi

4.8 out of 5 average rating, 238 reviews

Apartment in East Rogers Park

An outdoor terrace is visible, featuring seating arrangements with two orange chairs and a fire pit. The view overlooks Lake Michigan, with the calming waves in the background. A pathway leads down to the water, surrounded by the building's architecture.

Executive Apartment on Lake Michigan with parking

WalkabilityBeachAir conditioning

4.9 out of 5 average rating, 225 reviews

4.99 out of 5 average rating, 166 reviews

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

Spacious 2 Bedroom in the heart of Lakeview!

BeachWalkabilityBathroom

4.9 out of 5 average rating, 147 reviews

A comfortable living room features a blue sectional sofa adorned with soft throws, paired with a wooden coffee table. Natural light enters through large windows, highlighting a stylish armchair and an entertainment unit beneath a mounted TV.

Apartment in Evanston

Guest Favorite Escape Next to the Beach

WalkabilityViewCheckout

Holiday House Rentals with beach access

4.89 out of 5 average rating, 166 reviews

An open living area features a stone-finished fireplace and a large area rug. Two blue sofas, one with decorative cushions, frame the space. A wooden coffee table sits on the rug, with green plants enhancing the setting. Light flows in through nearby windows leading to the dining area.

Home in Downtown Chicago

Huge Downtown Gem *Yard *Parking *Fireplace

BeachWalkabilityAir conditioning

4.92 out of 5 average rating, 177 reviews

A charming two-story house is presented, featuring a welcoming front porch with seating. The entrance is accentuated by steps leading to a decorative stone feature. Sunlight enhances the exterior colors, and neighboring buildings are visible, showcasing a blend of architectural styles.

Home in West Rogers Park

House 5BED/3BATH/1PARKING close to Downtown & Lake

WalkabilityNearbyHospitality

4.98 out of 5 average rating, 100 reviews

A modern kitchen is presented with sleek white cabinetry and stainless steel appliances. An island with bar seating for six creates a central gathering space. Three pendant lights illuminate the area, while natural light enters through multiple windows, enhancing the airy ambiance.

Home in Wicker Park

Private Historic Coach House Wicker Park

WalkabilityWi-FiGetting around

4.84 out of 5 average rating, 184 reviews

A spacious spa room features a modern two-person jacuzzi, surrounded by elegant marble walls. The jacuzzi is designed with a clear accent panel, and amenities such as towels are neatly arranged nearby, promoting a calming and relaxing environment.

Home in Whiting

The Spa of Downtown Whiting

WalkabilityBeachLaundry

4.89 out of 5 average rating, 85 reviews

A modern living area features a curved sofa and two armchairs, arranged around a circular, striped rug. A flat-screen TV is mounted on the wall above a sleek fireplace. Natural light enters through large windows, complementing a dining area with a round table and multiple chairs.

Home in South Side

CasaNova Modern City Living

BeachViewLayout

5.0 out of 5 average rating, 21 reviews

Home in Downtown Chicago

Gold Coast Pristine 5BR|3.5BA| Patio| Parking

WalkabilityGetting aroundLocation

4.93 out of 5 average rating, 27 reviews

Home in South Side

B42: Spacious w/ Modern Art/Decor Mins to DWTN

WalkabilityLocationFamily

4.91 out of 5 average rating, 75 reviews

Home in Bronzeville

3BD | 2 Ensuites | Sleeps 8| Near Sox & McCormick

WalkabilityAccuracyTV

Holiday condos with beach access

Condo in East Rogers Park

A bright living room is furnished with a blue sofa, an ottoman, and a wooden coffee table. Large windows provide natural light and offer views of greenery outside. A white brick fireplace adds a cozy touch, while a small dining table is positioned near the windows.

1910 Beautiful Restoration! Walk to Beach!

WalkabilityViewLong stay

4.98 out of 5 average rating, 144 reviews

Condo in Downtown Chicago

A modern chef's kitchen is shown, featuring an island with seating for four. Sleek dark cabinetry contrasts with light countertops and stainless steel appliances. A bowl of fruit adds a touch of color, while glass pendant lights provide illumination above the island.

Modern MAG Mile 2BD/2BA (+Parking/Rooftop)

WalkabilityViewIndoor spaces

4.95 out of 5 average rating, 183 reviews

4.98 out of 5 average rating, 275 reviews

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

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

BeachWalkabilityKitchen

Condo in Downtown Chicago

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.

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

ViewWalkabilityLocation

4.87 out of 5 average rating, 228 reviews

4.78 out of 5 average rating, 722 reviews

A modern multi-story building is nestled among leafy trees, featuring large windows and a sleek, minimalistic design. A wooden staircase leads to the entrance, while blooming flowers add a touch of color to the landscaped garden in front.

Condo in Evanston

Spacious Evanston Unit - Walk to Northwestern U

BeachWalkabilityIndoor spaces

Condo in Downtown Chicago

The studio apartment features a spacious open layout with a comfortable bed, muted bedding, and a nightstand. A TV is positioned on a modern media unit, and a mini fridge adds convenience. Natural light filters in through a window, illuminating the neutral decor.

Studio flat in the heart of Chicago's Gold Coast

WalkabilityBeachComfort

4.73 out of 5 average rating, 264 reviews

4.87 out of 5 average rating, 291 reviews

A comfortable living area features a plush sectional sofa and a cozy armchair. A wooden coffee table is positioned centrally, while a television is displayed on a dark media unit. Natural light enters through multiple windows, highlighting the room's stone accent wall.

Condo in South Side

A Stones Throw from U Chicago South Campus!

WalkabilityViewBreakfast