Vacation rentals with lake access in South Loop

Find and book unique lake-access rentals on Airbnb

Top-rated lake-access accommodations in South Loop

Guests agree: these lake-access accommodations 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 Old Town
4.93 out of 5 average rating, 225 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!

Top guest favourite
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.
Condo in Gold Coast
4.95 out of 5 average rating, 142 reviews

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

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Parking spot on-site in/out access!! - Tranquil rooftop overlooks Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows

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, 218 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

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

Guest favourite
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
4.83 out of 5 average rating, 479 reviews

Lakeview Charmer -with parking!

Walk to Wrigley 4 blocks away: 15 min walk; 3 minute drive. Walk to The Vic (around the corner), the lake, several theaters, many restaurants, RedLine el (1 block) takes you north to Evanston, south to Loop, to Sox. Park your car behind the building. A Garden 2 BR (one semi-private; see pics) with 2 queen beds. With rollaway and couch, could accommodate up to 6. We also have a fold up crib. FYI: NO Smoking inside or on the patio. No animals. See pic on patio: el is a few doors west.

Guest favourite
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
4.99 out of 5 average rating, 161 reviews

KING bed FREE P-Spot EV EZZY Accessible NO stairs

You would enjoy staying in the spacious 1800 sq ft with 10 ft high ceilings. Two bedroom/2 bathroom apartment with direct access from the street level with ZERO STAIRS. It is an excellent solution for elder people and families with kids or maybe just a group of friends coming to have fun at the UNITED CENTER sports event or tourists as well as business folks or doctors to attend McCormick Place conferences. Bring the whole family to this great place with lots of room for fun.

Guest favourite
Condo in Grant Park
4.89 out of 5 average rating, 151 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!

Superhost
A modern living area features a large dark sofa and a glass coffee table atop a geometric patterned rug. Oversized windows provide views of the city and lake. A small dining area with sleek chairs and tropical plants adds a touch of greenery to the space.
Apartment in Streeterville
4.75 out of 5 average rating, 191 reviews

Modern Corner 2BR in Streeterville | Roof Deck | L

Stunning 1,200 square foot apartment with oversize windows, an open layout, and city/lake views in multiple directions. This bright and modern two bedroom, one bathroom corner unit is perfect for travelers looking for a stylish escape in the sky in downtown Chicago just off the Magnificent Mile and the lakefront. The building has great amenities including an amazing rooftop terrace with 360 degree views of the skyline and the lake. This is the best location in the city!

Top guest favourite
A well-lit bedroom features a spacious bed with decorative pillows, complemented by a cozy blue throw. A small desk with a chair is positioned near a window, which is adorned with blinds. Fresh flowers sit on the nightstand, enhancing the room's inviting appeal.
Apartment in Near North Side
4.94 out of 5 average rating, 200 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 two flights of stairs. Light sleepers should bring earplugs as there are noises typical of a big city.

Top guest favourite
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.
Condo in East Rogers Park
4.93 out of 5 average rating, 274 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.

Top guest favourite
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 Old Town Triangle
4.85 out of 5 average rating, 177 reviews

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.

Top guest favourite
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
4.97 out of 5 average rating, 313 reviews

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.

Top guest favourite
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
4.98 out of 5 average rating, 320 reviews

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.

Popular amenities for South Loop lake-access rentals

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Quick stats about vacation rentals with lake access in South Loop

  • Total vacation rentals

    Explore 40 vacation rentals in South Loop

  • Nightly prices starting at

    South Loop vacation rentals start at $124 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,920 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of South Loop vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across South Loop rentals

  • 4.9 Average rating

    South Loop stays are highly rated by guests—averaging 4.9 out of 5!

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