
Vacation rentals in South Loop
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Top-rated vacation rentals in South Loop
Guests agree: these stays are highly rated for location, cleanliness, and more.

The Metropolitan Retreat (Fitness Center • Sauna)
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, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Upscale High-Rise Apt · Rooftop Pool + Views
Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants - Paid parking nearby Unit Highlights: - Stunning views of the city - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modernly designed interior

Kasa | Spectacular City Views | Chicago
When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

South Loop 3BD 2BA Condo with Balcony and Parking
Stay in the heart of Chicago’s South Loop at this spacious 3-bedroom, 2-bath condo on Michigan Avenue. Enjoy easy access to Grant Park, Museum Campus, Soldier Field, McCormick Place, and the Lakefront Trail, with CTA trains and buses just steps away. This modern, walkable home features updated bathrooms and kitchen with new fixtures, hardwood floors throughout, a nice front deck, and an in-unit full-sized washer and dryer—perfect for families, groups, or business travelers.

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard. The property has a parking slab in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! Please reach out with any questions you may have before booking. NO CHORES! Hot tub 5-6 Person Spa

1BR South Loop Loft I SuperHost + Top Rated!
Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Lovely 1-bedroom serviced apartment near Museums!
Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Mich Ave Downtown Penthouse - Rooftop+Gym
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 -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!

LIVN West Loop Chicago 2 Bedroom
Experience modern city living at LIVN West Loop Chicago, a stylish loft style 2 bedroom apartment at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. Ideal for business travel, weekend stays, or longer visits, this newly renovated unit features a full kitchen, in unit washer and dryer, and modern interiors. Steps from Union Station and a short walk to Willis Tower, with easy access to dining, offices, and downtown attractions.

Pilsen Modern Chic Retreat
Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

Bright & Spacious Boho Oasis: A Warm Retreat
Discover a sun-drenched sanctuary that feels like a hidden gem. This isn't just a place to stay; it’s an airy, open-concept retreat designed for those who want to settle right in. With high ceilings and a "Modern Boho" aesthetic, the space is flooded with natural light and a warm, inviting ambiance. Nestled in a quiet, residential pocket of West Town, you’ll enjoy peaceful surroundings with the professional service of a 5-star host.

Spectacular Corner 3BR in the Loop | City Views
Stylish 1,400+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and fabulous city views in multiple directions. This dramatic light-filled three bedroom, two bathroom space is perfect for groups looking for a luxurious escape in the sky in the heart of downtown Chicago. Centrally located in a historic building close to everything you want to visit, this is the best location in the city!
Popular amenities for South Loop vacation rentals
Other great vacation rentals in South Loop

The Landing @ South Loop

Modern design with VU Skyward rooftop bar

Modern loft w/fast Wi‑Fi & smart TVs

Luxurious Bronzeville Apartment with RoofTop

South Loop Studio Hotel (304)

Modern 2BR Unit Rooftop & Gym Near McCormick Place

Warwick Allerton Hotel Chicago

A polished, modern affair on iconic Michigan Ave.
Quick stats about vacation rentals in South Loop

Total vacation rentals
Explore 490 vacation rentals in South Loop

Nightly prices starting at
South Loop vacation rentals start at R 489 ZAR per night before taxes and fees

Verified guest reviews
Over 25,320 verified reviews to help you choose

Family-friendly vacation rentals
290 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 130 rentals that welcome pets

Vacation rentals with a pool
120 properties feature pools

Rentals with dedicated workspaces
330 properties have a dedicated workspace

Wi-Fi availability
480 of South Loop vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across South Loop rentals

4.8 Average rating
South Loop stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Rentals with a sauna South Loop
- Rentals with lake access South Loop
- Rentals with a fireplace South Loop
- Rentals with a patio South Loop
- Family-friendly rentals South Loop
- Pet-friendly rentals South Loop
- Rentals with outdoor seating South Loop
- Condo rentals South Loop
- Rentals with a hot tub South Loop
- Rentals with a fire pit South Loop
- Fitness-friendly rentals South Loop
- Rentals with pools South Loop
- Rentals with a washer and dryer South Loop
- Smoking-friendly rentals South Loop
- Apartment rentals South Loop
- Rentals with an EV charger South Loop
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Soldier Field
- 875 North Michigan Avenue
- The Field Museum
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Union Park
- University of Chicago
- Lincoln Park Zoo
- Chicago River Walk
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Washington Park Zoo
- Loyola University Chicago
- Indiana Dunes State Park
- Oak Street Beach
- Illinois Beach State Park





