Vacation rentals in South Loop

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in South Loop

Guests agree: these stays are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Top guest favorite
A spacious living area features a comfortable black leather sofa and a distinctive black chair. Natural light filters through large windows, illuminating the mid-century cabinetry and vibrant area rug. Light-colored curtains frame the windows, and a circular coffee table sits at the center.
Guesthouse in Little Italy
4.99 out of 5 average rating, 903 reviews

Polk Street Coach House Apartment, Little Italy/Medical Dist

Cook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs. Welcome to Polk Street Guest House: a well-appointed, completely private, 2-bedroom carriage house in Little Italy near the Medical District. Decorated with mid-century antiques and paintings, our 2nd floor coach house apartment is perfect for guests looking for a home-away-from-home. It has a fully-equipped kitchen, teak furnishings, comfortable queen size beds, and a private entrance accessible though a side gate from the street. For folks with kids, please note there is no child gate near the top of the stairs. Enjoy quiet parks and have easy access to all of Chicago. Major hospitals at Rush, University of Illinois, Hines, VA and Stroger are within 3 to 6 blocks. Chicago's elevated pink line train is 2 blocks away; the Blue line is 3 blocks. Take a quick cab ride to “the loop" downtown for $10, or take a Divvy bike. Chicago's famed Little Italy restaurants on Taylor Street are a block South. Free street parking with 24-hour zoned pass. Your hosts: Ken & Curt Want privacy? You have privacy! Use an entry code to access the coach house through the side gate to the left of our main house. Your private entrance, which also has keypad entry, is on the left side of the vine-covered brick building in back. The main living area is upstairs. There will be a 24-hour zoned parking pass waiting for you on a shelf as you enter the Coach with instructions on how to fill out the parking pass. We regret that the Coach House is not ADA/wheelchair accessible. For those arriving early than check-in, or who are staying later than check-out, we have an area beneath the coach house where you may leave your luggage. Just ask. Our space is your space. The coach house is entirely separate from our main house where we live. The coach house has a separate entrance and full amenities. You’re welcome to use the seating area in the courtyard, and the Weber grill. We're happy to provide any tips about the city, or to help show you how to use anything in the apartment. Just call our cell phones (they are listed in the apartment), or step across the yard and say hello. Three blocks to the Medical District and major hospitals, walk from this tree-lined Little Italy neighborhood to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Indian cuisine on Taylor Street. Stroll in Garibaldi Park on the doorstep, with Arrigo Park a block away. We are conveniently located for transit, bike, car and Uber. Public Transportation: -Pink Line, Polk Station, CTA: 3 blocks west of us, this rail line gets you downtown in 10 minutes (plan 30 minutes total time with walking for most destinations) and is useful for most site-seeing. -Blue Line, Racine Station, CTA: 4 blocks east or west of us, this rail line gets you to O'Hare airport in less than an hour, or downtown in about 10 minutes (it's a bit longer walk to the Blue Line than to the Pink Line) . -#157 Bus (Streeterville): This super convenient bus 1 block south of us on Taylor Street runs during the daytime only and takes you to the Magnificent Mile for upscale shopping on North Michigan Avenue in 25 minutes. -#12 Bus (Roosevelt): This is about 3-4 blocks south of us, runs east-west, and takes you to the Soldier Field stadium and the Roosevelt Road shopping area with Whole Foods, Nordstrom Rack, Best Buy, Core Power Yoga, and much more. Bicycle: You bike? We bike. There is a DIVVY bike share station a block east in Arrigo Park. Get at DIVVY bike-share 24-hour pass with unlimited half-hour rides. Switch out bikes for longer distances. If you have your own bike, you can park it safely on the ground floor of your coach house apartment. It takes 15 to 20 minutes to bike to most downtown locations. Car: Our home is 3 blocks south of I-290 (the Eisenhower), and near I-55 (the Stevenson), I-90 and I-94 (the Dan Ryan and Kennedy). Parking: We provide parking passes for free zoned street parking available on a small shelf as you enter the Coach House along with instructions. Please be very careful about filling out the pass, as City workers seem motivated to issue tickets if the pass is not filled out correctly. We travel a lot and know what it's like to be away from home. That's why we've furnished the apartment with appealing furniture, comfortable beds, plenty of towels (and more towels), soaps, shampoos, and a kitchen outfitted with all the basics plus a few more: Kitchen Aid food processor, toaster, microwave, baking and cooking tools, Calphalon pots & pans. Please note there is no dishwasher. Enjoy complimentary Nespresso coffee, Bigelow teas, bottle water, and snacks. Three blocks to the Medical District. Walk the tree-lined streets of the Little Italy to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Asian cuisine on Taylor Street. Stroll in Garibaldi Park steps away, or Arrigo Park a block away.

Top guest favorite
A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.
Apartment in Lincoln Park
5 out of 5 average rating, 295 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Guest favorite
An outdoor pool is surrounded by lounge chairs in various colors, creating a bright and inviting atmosphere. Tall buildings are visible in the background, and the pool reflects the clear blue sky overhead.
Apartment in South Loop
4.9 out of 5 average rating, 115 reviews

The Executive's Escape (2BD / 2BA)

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.

Guest favorite
An ivy-covered brick facade presents a charming entrance. A black door with decorative window details is centered, flanked by a small garden featuring well-maintained greenery. A gravel pathway leads to the entrance, showcasing the unique character of the historic coach house.
Guesthouse in West Loop
4.87 out of 5 average rating, 468 reviews

Pro Cleaned & Isolated West Loop Coach House

Mimi & Paul's historic ivy-covered two-level coach house has a private entrance and an airy queen bedroom. The renovated kitchen is outfitted with European-sized appliances, though you'll probably have no time to cook since you're surrounded by the best restaurants Chicago has to offer. All of the essentials are provided to make your stay easy and comfortable...paper products, soaps, shampoo/conditioner/body wash, towels, linens and even coffee/tea! (See layout in "Other Details To Note" below)

Guest favorite
A spacious bed layered with a colorful patterned blanket is positioned near large glass doors that open to a private deck. Sheer curtains frame the entrance, allowing natural light to fill the room while offering a view of the greenery and flowers on the deck.
Guest suite in South Loop
4.93 out of 5 average rating, 153 reviews

Entirely Private Suite - Urban Oasis - Pilsen/UIC

Pilsen - McCormick Place - Soldier Field - Thalia Hall - UIC - Chinatown - South Loop - Radius Welcome to a brand new, entirely private, spacious and peaceful oasis in Pilsen-UIC with a smartlock system and self check in. Central location near some of the hottest neighborhoods, restaurants, concert and tourism venues, and minutes from the Loop! Full bath with a luxurious spa shower, cable, wifi, flatscreen tv, refrigerator, iron, desk, coffeemaker, toiletries and a lovely private deck.

Top guest favorite
The living area features large windows allowing ample natural light, complemented by a sleek TV and modern seating arrangements. A plush orange rug anchors the space, while a circular coffee table sits at its center, enhancing the room's inviting atmosphere.
Apartment in South Loop
4.92 out of 5 average rating, 237 reviews

The South Loop Reserve I Sleep 6 I Top Rated

Modern & ultra spacious 2-bedroom loft in Chicago's South Loop. Central location to Grant Park, Soldier Field, Museums, McCormick Place and more! With a walk & transit score of 97, enjoying Chicago's fantastic restaurants, bars, and shopping options is a breeze. Our loft gets incredible natural light, has luxuriously tall ceilings and plenty of room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide.

Guest favorite
Condo in Grant Park
4.89 out of 5 average rating, 150 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!

Guest favorite
A comfortable living area with a gray sofa adorned with patterned pillows and a throw, set against exposed wooden beams. A glass coffee table holds decorative items, while a dining area with upholstered chairs is visible in the background. Soft lighting enhances the inviting space.
Apartment in South Loop
5 out of 5 average rating, 17 reviews

Luxéry Stay "Chicago" - McCormick & Wintrust Area

Staying in one of Chicago's Historical Buildings, you can now experience living in the famous South Loop neighborhood conveniently located across from McCormick Place! South loop has a teeming restaurant scene with front row access to Grant Park, the lakefront Museum Campus and Soldier Field! this area is unmatched by most urban neighborhoods. Explore the celebrated jazz clubs, and other historic areas like industrial Motor Row and the charming Prairie Avenue District.

Top guest favorite
A modern living space features a light-colored sofa with decorative pillows and a woven throw. A warm-toned wooden accent wall complements a sleek electric fireplace below a mounted television. A patterned area rug anchors the room, while shelves in the background display decorative items.
Loft in South Side
4.99 out of 5 average rating, 132 reviews

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

Top guest favorite
A spacious common area features large windows that allow plenty of natural light to fill the room. A modern entertainment unit is placed against a white brick wall, complemented by a comfortable sectional sofa and a round coffee table on a textured rug.
Apartment in South Loop
4.94 out of 5 average rating, 222 reviews

Lavish 2BR/2BA Loft I Next to Grant Park & Museums

Enjoy Chicago in our modern & spacious 2-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!

Superhost
The kitchen area is equipped with modern appliances, including a stainless steel refrigerator and a microwave. A breakfast bar with four stools is highlighted by stylish pendant lighting, while a glass coffee table with greenery decorates the living space. The entryway features a secure door.
Apartment in South Loop
4.89 out of 5 average rating, 44 reviews

Modern Stylish 1BR, Free Parking, Prime Location"

Just a few blocks away from Downtown Chicago, The Loop, and popular attractions, this property is the ideal spot for your stay! Carefully designed and fully furnished, the unit offers excellent amenities for both comfort and entertainment: Fully equipped kitchen In-unit laundry Roku TV in the bedroom (bring your own Netflix/Hulu login) Fast WiFi Perfect for healthcare workers, corporate employees, and all travelers seeking a convenient and cozy place to call home!

Guest favorite
A modern kitchen features sleek black cabinetry and appliances, complemented by a contrasting white countertop. Stylish stools are arranged around a small kitchen island. The wall is adorned with a framed painting, while decorative items are displayed on open shelves above the countertop.
Apartment in Lower West Side
4.87 out of 5 average rating, 300 reviews

Spectacular Pilsen Studio for 2!

This chic studio in the heart of Pilsen is the perfect space to kick back and relax during your visit to the Windy City! The vibrant neighborhood always has something to offer to any type of traveler, and it's a quick trip to see most of the iconic Chicago sights. Easily walk to historic Thalia Hall, or drive to the Loop in just 5 minutes! You'll love the thoughtful touches and modern decor in the apartment, as well as the bright and welcoming main space.

Popular amenities for South Loop vacation rentals

When is the best time to visit South Loop?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price€ 102€ 112€ 139€ 164€ 197€ 210€ 222€ 210€ 188€ 206€ 141€ 134
Avg. temp-3°C-1°C4°C10°C16°C22°C25°C24°C20°C13°C6°C0°C

Quick stats about vacation rentals in South Loop

  • Total vacation rentals

    Explore 510 vacation rentals in South Loop

  • Nightly prices starting at

    South Loop vacation rentals start at € 34 per night before taxes and fees

  • Verified guest reviews

    Over 24,770 verified reviews to help you choose

  • Family-friendly vacation rentals

    280 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 150 rentals that welcome pets

  • Vacation rentals with a pool

    140 properties feature pools

  • Rentals with dedicated workspaces

    330 properties have a dedicated workspace

  • Wi-Fi availability

    500 of South Loop vacation rentals include wi-fi access

  • Popular amenities for guests

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

  • 4.7 Average rating

    South Loop stays receive an average rating of 4.7 out of 5 from guests

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. South Loop