
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.

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!

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

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

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.

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.

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!

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!

*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.

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.

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.

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.

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
Lake-access house rentals

Gold Coast Home|Rooftop |PoolTable |Parking |Views

Spacious Two Story Luxurious Home w/Outdoor Deck!

Amazing Location! Spacious Duplex Getaway

Amazing historic campus mansion!

Bronzeville 42: Art & Hospitality Mins to Downtown

CasaNova Modern City Living

Luxury Home - Pool Tbl/Bar/Patio

The Spa of Downtown Whiting
Lake-access apartment rentals

Spacious Vintage 3 BR in Chicago's NorthCenter!

Charming, Sunny Apartment with Backyard Garden

The Lakefront Lookout (2BR)

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

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

Charming Apt.Fully Equipped Prk.Inc 12 min 2 Lake

minimal lakefront apartment

Luxury Designer Penthouse | Gold Coast/Old Town
Other vacation rentals with lake access

Bronzeville Bohemian Loft

Cozy 1BR in South Loop | Convenience in the City

The Beach Loft/ 30 min from Chicago Navy Pier

Wicker Park - Garden At The Heart of It All

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |

Executive Apartment on Lake Michigan with parking

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

2bd/2bath Urban Loft w/ 2 pkg spots 1 blk to train
When is the best time to visit South Loop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $152 CAD | $164 CAD | $225 CAD | $276 CAD | $288 CAD | $305 CAD | $455 CAD | $397 CAD | $375 CAD | $299 CAD | $263 CAD | $225 CAD |
| Avg. temp | -3 °C | -1 °C | 4 °C | 10 °C | 16 °C | 22 °C | 25 °C | 24 °C | 20 °C | 13 °C | 6 °C | 0 °C |
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!
Destinations to explore
- Rentals with a sauna South Loop
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- Rentals with pools South Loop
- Condo rentals South Loop
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- Rentals with a fireplace South Loop
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- Family-friendly rentals South Loop
- Rentals with a washer and dryer South Loop
- Rentals with a patio South Loop
- Rentals with an EV charger South Loop
- Rentals with a firepit South Loop
- Smoking-friendly rentals South Loop
- Rentals with lake access Chicago
- Rentals with lake access Cook County
- Rentals with lake access Illinois
- Rentals with lake access United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Oak Street Beach
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- The Beverly Country Club
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Illinois Beach State Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark




