Holiday rentals with beach access near Navy Pier

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.

4.89 out of 5 average rating, 175 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.

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.

4.94 out of 5 average rating, 252 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!

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, 144 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

4.81 out of 5 average rating, 234 reviews

The Lakefront Lookout (Rooftop Deck • Gym)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, Navy Pier, Riverwalk, Soldier Field, The Field Museum, Oak Street Beach, and more. Additionally, guests are merely blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city!

An expansive rooftop patio is showcased, featuring woven outdoor couches with blue cushions arranged around a glass-top table. The city skyline is prominently visible, with notable buildings punctuating the clear blue sky, complemented by touches of lush greenery.

4.98 out of 5 average rating, 120 reviews

Private Downtown Retreat with Rooftop Oasis

Welcome to your exclusive retreat in the heart of the city, where urban sophistication meets unparalleled comfort. Nestled in between Magnificent Mile and Gold Coast, this luxurious Airbnb offers a haven of style and tranquility amidst the hustle and bustle. The rooftop patio offers incredible views of the city skyline, with touches of lush greenery. The spacious living areas boast oversized windows that flood the space with natural light. Each bedroom is a sanctuary where luxury meets comfort.

4.82 out of 5 average rating, 249 reviews

Townhouse

Historic luxury townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after locations in the city! Located on one of Chicago’s famous streets, you’ll be a 5-minute walk from the historic Gold Coast beach and intimate views of Lake Michigan. The property is also within walking distance of the subway, where you can connect to the L trains, and the Magnificent Mile. It is the perfect place to stay for adventurous travellers and those who fancy a beach in the City!

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.

4.95 out of 5 average rating, 121 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.

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.

4.96 out of 5 average rating, 106 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!

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.

4.95 out of 5 average rating, 299 reviews

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.

A modern living area features a comfortable sectional couch, complemented by decorative pillows. Natural light enters through large windows, illuminating the space. A flat-screen TV is positioned on a wooden media console, and a dining area with a bar counter is visible in the background.

4.91 out of 5 average rating, 114 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 | 1st 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)

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, 157 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.

4.95 out of 5 average rating, 152 reviews

Urban Oasis in Vibrant Gold Coast

Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, we are 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 rentals with beach access near Navy Pier

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

4.99 out of 5 average rating, 114 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.

Flat in Evanston

Evanston 2BR 2Bth 1 Blk to Beach

A cozy living room features a large smart TV mounted on the wall, and a plush sectional sofa with a soft throw draped over it. Armchairs are positioned nearby, alongside a wooden bookshelf. A vibrant area rug adds warmth to the space, with a window letting in natural light.

4.92 out of 5 average rating, 150 reviews

The Loyola Garden Flat: Huge 2BR Near Lake

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.

4.81 out of 5 average rating, 232 reviews

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

4.8 out of 5 average rating, 108 reviews

A bright living area features a light-colored sofa accompanied by a dark green armchair. A coffee table with decorative items sits in front of the couch. Framed artwork adorns the walls, and large windows allow natural light to fill the space.

Flat in Evanston

Spacious and Newly Renovated 1BR Next to the Beach

A modern kitchen is showcased with sleek black countertops and white cabinetry. A tall chair is situated at the kitchen island, providing seating for one. Stainless steel appliances, including a gas stove and microwave, are visible, complemented by warm yellow walls that enhance the space's brightness.

4.83 out of 5 average rating, 150 reviews

Andersonville Garden Living

4.77 out of 5 average rating, 265 reviews

Cozy Bedroom in Wrigleyville (Entire Apt)

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.

4.99 out of 5 average rating, 159 reviews

Spacious 2 Bedroom in the heart of Lakeview!

A dining area features a round wooden table surrounded by six chairs, enhanced by soft lighting. Exposed stone walls and large windows contribute to a cozy ambiance, while potted plants add a touch of greenery.

4.93 out of 5 average rating, 228 reviews

Inspiring Stone Grotto Sleeps 10-20 & Free Parking

House rentals with beach access

4.9 out of 5 average rating, 73 reviews

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

4.95 out of 5 average rating, 22 reviews

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

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.

4.91 out of 5 average rating, 174 reviews

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

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.

4.9 out of 5 average rating, 80 reviews

CasaNova Modern City Living

An open living space showcases a plush blue seating area with decorative pillows, flanked by two side tables. In the background, a dining area is visible, furnished with a dark wood table and six chairs, illuminated by natural light through large windows.

4.83 out of 5 average rating, 12 reviews

Ideal Group Getaway: Best Location, Parking, Patio

A cozy living room features a dark leather sectional sofa with colorful throw pillows. A wooden coffee table sits in the center, adorned with a floral arrangement. Blue walls are complemented by dark curtains, and a television is positioned against the wall.

4.88 out of 5 average rating, 25 reviews

Cozy 4-Bedroom House with Patio

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.

4.98 out of 5 average rating, 98 reviews

Private Historic Coach House Wicker Park

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.

4.95 out of 5 average rating, 99 reviews

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

Apartment rentals with beach access

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.

4.87 out of 5 average rating, 284 reviews

A Stones Throw from U Chicago South Campus!

The kitchen and dining area feature a large marble table surrounded by black chairs, with a plush area rug underneath. A modern kitchen is equipped with stainless steel appliances and a large island with additional seating. Floor-to-ceiling windows provide natural light and views of the outside greenery.

5 out of 5 average rating, 28 reviews

Huge Boho Luxury Condo | Parking + XL Balcony

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.

4.98 out of 5 average rating, 265 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

The living area features hardwood flooring and blue upholstered sofas with cushions. A light, modern coffee table sits in front of the seating area. The space is illuminated by natural light through nearby windows, enhancing its airy feel.

4.85 out of 5 average rating, 47 reviews

South Shore Dr Retreat

A spacious living area features a modern sectional sofa facing a sleek fireplace and a light wooden mantle. A dining table with white chairs is visible, complemented by natural light from the recessed lighting and open layout leading into the kitchen area.

4.8 out of 5 average rating, 54 reviews

2 BR condo in the heart of Old Town

A lush garden area showcases a variety of blooming flowers surrounded by greenery. The path is lined with vibrant floral colors leading up to the brick building, which features large windows allowing natural light to fill the space.

4.98 out of 5 average rating, 91 reviews

Jarvis Gardens - 1BR/BEACH/Wine patio/fire pit

A modern living room is presented, featuring a brown leather sofa and two armchairs with light upholstery. A round wooden coffee table sits at the center, accompanied by two textured stools. Two mirrors adorn the wall above the sofa, while large windows allow natural light to fill the space.

4.97 out of 5 average rating, 64 reviews

The ModernFarmhouse Chicago-Near Downtown Chicago

4.78 out of 5 average rating, 715 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.

Apartment in Evanston

Spacious Evanston Unit - Walk to Northwestern U

Other holiday rentals with beach access

4.91 out of 5 average rating, 79 reviews

A cozy living area features a light-colored sofa adorned with a textured throw and a contemporary black-and-white artwork on the wall. A sleek kitchen island with two bar stools sits adjacent to the living space, illuminated by pendant lighting. Large windows provide a view of the outdoor greenery.

Guest suite in Chicago

Comfy suite w/ steam shower near McCormick Place

4.9 out of 5 average rating, 41 reviews

Upscale High-Rise Apt · Rooftop Pool + Views

4.91 out of 5 average rating, 22 reviews

Luxury Designer Apartment 803| Gold Coast/Old Town

4.65 out of 5 average rating, 144 reviews

Prime Lincoln Park Studio Apt with Free Parking

5 out of 5 average rating, 7 reviews

Luxury South Loop Apt

5 out of 5 average rating, 25 reviews

Stylish Hyde Park/Kenwood Brownstone Garden Apt

4.96 out of 5 average rating, 413 reviews

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.

Guest suite in Chicago

Gorgeous, cozy 1-bedroom Suite in Andersonville

A spacious bedroom features a four-poster bed draped with a sheer canopy, complemented by turquoise bedding. A colorful accent pillow adds detail. The room includes a desk with a chair and a small decorative arrangement on the side table. Natural light enters through near sheer curtains.