Vacation rentals with lake access in South Loop

4.93 out of 5 average rating, 230 reviews

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 Old Town

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!

4.75 out of 5 average rating, 279 reviews

A bright living area features a comfortable gray sofa and two modern chairs set around a round coffee table. Large windows provide expansive views of the city, while greenery adds a touch of nature to the space. The warm lighting creates a welcoming ambiance.

Apartment in The Loop

Stunning 3BR Penthouse in the Loop | Roof Deck

[NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2nd rooftop remains open and available for guests to use.] Beautiful 1,400+ square foot penthouse apartment on the top floor with 13 foot tall ceilings, oversize windows, and panoramic city views. This bright and airy three bedroom, two bathroom space is perfect for travelers looking for a luxurious escape in the sky in the heart of downtown Chicago. The penthouse is adjacent to the buil

4.98 out of 5 average rating, 223 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

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 $10/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

4.97 out of 5 average rating, 537 reviews

A light-filled living room features a comfortable beige sofa with an accent pillow and a light throw. Adjacent windows allow natural light to stream in, highlighting the wooden flooring and decorative area rug. A small side table holds a lamp, contributing to the calm atmosphere.

Apartment in Evanston

Charming, Sunny Apartment with Backyard Garden

House of the Blue Doors Enjoy staying with us in this spacious 1st floor flat. Furnished by the resident designer in tasteful neutrals, original curated artwork, one of a kind furniture and accent pieces. Sip morning coffee or a glass of wine in the sunlit kitchen or front porch, fire up the backyard grill for a barbecue. Soak in the award winning Chicago ceramic artist designed and made floor in the bathroom. Close to Northwestern, Chicago, Lake Michigan, everything Evanston offers.

4.94 out of 5 average rating, 126 reviews

The living area features a spacious gray sectional sofa complemented by a textured area rug. A sleek coffee table is adorned with decorative items, while a stylish arc floor lamp provides ambient lighting. In the background, a dining space with a round table and four chairs is visible.

Condo in Gold Coast

GLORIOUS GOLD COAST GETAWAY

Welcome! 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. We look forward to hosting you!

4.82 out of 5 average rating, 123 reviews

The image displays a vibrant living space featuring a blue couch and a retro PacMan machine, adding a touch of fun. A workspace with a desk is present, and the kitchenette is visible in the corner, equipped with essentials. Soft lighting enhances the overall ambiance.

Apartment in Avondale

Heart of Logan Sleeps 5 - Games - Great Area

Located in beautiful Avondale/Logan Square!!! Comfy 650 sqft 1BR 1BA with 2 beds 3rd floor apt Tub/shower, games for adults & kids 1 Large bedroom with queen bed 1 sleeping nook with twin bed 1 air mattress 1 Roku Smart TVs, free wifi (400 mpbs speed) Sleeps 4 comfortably Street parking Walking distance from bars/restaurants/stores Great for professionals and travelers Minutes from hip Logan Square and Wicker Park PermitS Street Parking - permits provided Very quiet and safe

4.9 out of 5 average rating, 153 reviews

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.

Condo in Grant Park

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!

Apartment in Near North Side

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.

4.96 out of 5 average rating, 271 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.

Condo in East Rogers Park

A well-lit living area features a striped sofa accompanied by two modern armchairs. A wooden coffee table sits in the center, complemented by a patterned rug. Shelves display an array of silverware and decorative items, adding character and visual interest to the space.

4.93 out of 5 average rating, 275 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This cozy AirBnb is perfectly situated. A beautifully clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation & restaurants, red line "El" trains & bus routes. Apt has private, queen bedroom, en suite full bathroom, living room w/queen sofa bed, TV, dining table, & partial kitchenette. NOTE: No full kitchen.

4.97 out of 5 average rating, 318 reviews

A spacious living area is furnished with a light-colored sofa, two armchairs, and an entertainment unit containing books. Soft lighting from a lamp creates a warm atmosphere. A geometric area rug adds visual interest to the carpeted floor. The sloped ceiling enhances the cozy feel of the space.

Apartment in Uptown

Cozy loft in Chicago's Uptown

Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; apartment on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. Andersonville (one of Chicago’s coolest neighborhood is a 15-minute stroll. CTA's Red Line/Wilson train station is 3 blocks away. Overnight street-parking decals also available for guests.

4.98 out of 5 average rating, 324 reviews

A spacious living area is presented, featuring a large gray sectional sofa. Natural light enters through expansive windows, illuminating the room. A fireplace and a mounted television are visible on the wall, with plants enhancing the decor around the space.

Condo in Uptown

Near Lake Michigan & Wrigley Field

Available 2B/2B condo with 2 King Size Beds. One block from the Aragon Ballroom and Riviera with great views of Uptown and two blocks from Lake Michigan. It’s also a perfect place to stay if your in town for a Cubs game. You can see the stadium from the rooftop deck. Walking distance to everything you need, 2 train stations, groceries, gym, restaurants/ bars. The perfect place to come and go as you please with easy key code entry.

Townhouse in Ranch Triangle

A spacious living area showcases a comfortable L-shaped leather sofa adorned with decorative pillows. A glass coffee table is positioned on an elegant area rug, while framed art pieces decorate the walls. A floor lamp provides soft lighting next to a small side table with a decorative plant.

4.98 out of 5 average rating, 303 reviews

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit

This generously sized, quiet apartment, located in the highly sought-after Lincoln Park neighborhood, offers convenient access to acclaimed restaurants and boutiques, all within a five-minute walk. Its private entrance and proximity—less than four blocks—to both the Red and Brown Line "L" stations ensure effortless access to Chicago's attractions, most within a two- to five-stop train ride. Zoned parking permits are provided.

Popular amenities for South Loop lake access rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Lake access house rentals

4.9 out of 5 average rating, 161 reviews

A spacious living room is furnished with two comfortable sofas and a wooden coffee table. A large black-and-white cityscape photograph is displayed on the wall. Natural light fills the room through windows, highlighting the polished wood floors and decorative ceiling. A dining area is visible in the background.

Home in Lake View

Spacious Two Story Luxurious Home w/Outdoor Deck!

4.98 out of 5 average rating, 44 reviews

A bright bedroom features a metal bed frame with a spacious white bedding set. Two nightstands with lamps are positioned on either side. Natural light filters through the large window, highlighting the room's neutral walls and wooden flooring.

Home in Evanston

Amazing Location! Spacious Duplex Getaway

5 out of 5 average rating, 37 reviews

The exterior of a historic brick home features a prominent gable roof and leaded windows. Lush greenery surrounds the property, highlighted by manicured shrubs and trees. A pathway leads to a welcoming entrance, inviting guests to explore the beautiful architecture of the residence.

Home in Hyde Park

Amazing historic campus mansion!

4.9 out of 5 average rating, 70 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 Chicago

CasaNova Modern City Living

Home in Old Town Triangle

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.

4.86 out of 5 average rating, 182 reviews

Historic Old Town, Fabulous 4 Bedroom Home

4.86 out of 5 average rating, 7 reviews

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.

Home in Old Town

Ideal Group Getaway: Best Location, Parking, Patio

4.99 out of 5 average rating, 91 reviews

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.

Home in Near North Side

Private Downtown Retreat with Rooftop Oasis

Home in Old Town Triangle

A stylish living area features a black leather chesterfield sofa adorned with plush white pillows. A glass coffee table rests on a decorative area rug, while elegant chandeliers hang from the ceiling. The backdrop reveals an open kitchen with cabinetry, enhancing the room's sophistication.

4.98 out of 5 average rating, 89 reviews

Opulent 3bdr2bth Old Town Luxury + Parking prmts

Lake access apartment rentals

Apartment in North Center

A bright dining space features a round table surrounded by wooden chairs, complemented by natural light from large windows. A decorative rug lies beneath the table, and a vintage wooden display cabinet occupies one wall, showcasing various items. A plant is seen near the window.

4.9 out of 5 average rating, 224 reviews

Spacious Vintage 3 BR in Chicago's NorthCenter!

4.99 out of 5 average rating, 164 reviews

A spacious living area features a large gray sectional sofa adorned with yellow accent pillows. A round wooden coffee table sits in front, with decorative items arranged on it. Two framed artworks are displayed on the wall beside a tall green plant, contributing to a modern aesthetic.

Apartment in West Town

KING bed FREE P-Spot EV EZZY Accessible NO stairs

4.83 out of 5 average rating, 181 reviews

A modern living area features a light green sectional sofa adorned with dark blue accent pillows. A decorative area rug with a subtle pattern is positioned beneath a glass coffee table. Natural light filters through sheer curtains, and a plant adds a touch of greenery.

Apartment in South Side

The Posh Apt. Mins to Downtown & Hyde Park

Apartment in Lincoln Park

A comfortable living area is presented, featuring a brown sofa, light teal chairs, and a white coffee table. Soft lighting is provided by two lamps on either side of a teal accent table. Natural light filters through the window shutters, enhancing the cozy ambiance.

4.98 out of 5 average rating, 412 reviews

Lincoln Pk-parking-wifi-King bd-crib-kid friendly

4.89 out of 5 average rating, 110 reviews

A spacious living room features a cozy seating area with two leather sofas facing a modern TV stand. A light-colored coffee table is positioned between the sofas, and a decorative painting hangs above the fireplace. Large windows with blinds allow natural light to fill the space.

Apartment in Uptown

Elegant 2-bed/2-bath in the heart of Uptown

4.83 out of 5 average rating, 482 reviews

A cozy living area is highlighted by a red accent wall and brick details. A comfortable blue sofa faces a mounted television, with a striped chair nearby. A mirror and decorative plant are positioned against a stylish cabinet, complementing the space's inviting layout.

Apartment in Lake View

Lakeview Charmer -with parking!

4.96 out of 5 average rating, 122 reviews

Apartment in South Shore

420 at Cheltenham 4BR

4.9 out of 5 average rating, 117 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

New renovation|1BR|Stylish|Modern|Next to the Lake

Other vacation rentals with lake access

4.67 out of 5 average rating, 115 reviews

A wooden-framed sign with a black background features white letters that spell 'WELCOME TO THE LANDING' at the center. The sign is placed on a smooth, light-colored surface, conveying a welcoming message.

Apartment in South Loop

The Landing @ South Loop

4.9 out of 5 average rating, 20 reviews

A modern living area is highlighted by a mounted flat-screen TV above a patterned fireplace. A sleek cabinet houses decorative items. A coffee table with a tray sits on a textured rug, accompanied by potted plants and a stylish lamp, creating a balanced ambiance.

Apartment in Bronzeville

Bronzeville Bohemian Loft

Apartment in Andersonville

5 out of 5 average rating, 21 reviews

3BD 2BR | Design Stay | Green Mill, Clark St, Lake

Condo in East Rogers Park

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.

4.97 out of 5 average rating, 77 reviews

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

5 out of 5 average rating, 10 reviews

Apartment in Grant Park

60th Flr Lake Views, A Stay Above It All, Sleeps 5

Apartment in Magnificent Mile

4.99 out of 5 average rating, 85 reviews

Luxury 3BR Duplex in Prime Location

Vacation home in Jackson Park Highlands

The living room features a comfortable gray sofa and a wooden coffee table set on a soft area rug. A Smart HDTV is positioned against a wall, while natural light enters through a large window adorned with light curtains. Decorative lighting fixtures enhance the space.

4.94 out of 5 average rating, 88 reviews

UChicago Luxurious King Suite Lakefront