The Loop is a buzzing tourist area with numerous attraction sights, parks, theatres, shopping stalls and most of all it is home to the 108-story Willis Tower. Meanwhile, you can also check out the Grant Park which features the large, rococo-style Buckingham Fountain and hosts annual events like the Taste of Chicago and Lollapalooza which is a renowned gig in this part of America. While visiting this incredible city, you don’t need to worry where you are going to be stay because here with me is a great list of the best Vrbo accommodations near the South Loop, which you can rent for your stay here. Make sure to plan a visit to this amazing city and check out its amazing wonders as you stay in these amazing accommodations.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on May 25, 2025.
1. Apartment with minimalistic style
This is a stunning two-bedroom apartment with a vintage touch to it. It features a sleek and sophisticated front hall that leads past a stylish fully equipped kitchen, a spacious living room, free internet, cable TV, amazing air conditioning, a lawn and patio at the back. With its perfect proximity to the city, you will have access to the finest surrounding amenities and world-class restaurants which will honestly crown your holiday experience.
Accommodates: 5
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Host:
The owner was very responsive quick to answer every questionKai is friendly and gave us many tips of places to visit and eat Thanks for a great stayThe owner was extremely easy to deal withThe property was clean and very well appointed Perfect for the three of us Great to have a kitchen for eating inLike nice umbrella become very handy and useful when you stay while outside is pouringLocation:
well stocked and in a quiet neighborhoodThe neighborhood is established with lots of characterIt was also located in a great part of town near stores and restaurantsIt is located in the middle of fabulous attractions but not too close to noisy trafficGreat place and loved walking distance to Claremont Diner Great food and fast serviceCleanliness:
but it didn't matter as everything was exactly as describedWe enjoy the apartment and everything is clean and thoughtfully with care of patronsThe neighborhood was quiet and folks were friendlyVery clean and updated unit in historic row house neighborhoodRead more reviewsAmenities & Room:
We appreciated the toiletries and little extras in the kitchenInside it is very spaciousa parking garage is the cherry on topGreat location spacious bed rooms beautiful kitchenIt was treat to have 2 bedrooms and bathrooms
2. A cozy holiday rental in the South Loop area
Make sure to check out this modern and rustic home. This three-bedroom house is located in Chicago’s vibrant Pilsen neighborhood in a serene street just a walking distance from Downtown Chicago. This house features keyless entry, ultra high-speed Wifi, high definition smart TV’s (with HBO, Netflix, and Hulu), a fully stocked kitchen with an open plan, washer and dryer, master bath with hot tub, walk-in closet, complimentary coffee and tea, and private parking. Whether you are exploring all this wonderful city or attending a business convention, this home will provide a comfortable and safe stay in the proximity of everything perfect for a weekend getaway.
Top guest reviews
Host:
the garage was a great benefit during the massive snow storm that came through Very attentive ownersAnd our hosts were so congenial and easy to work with-- making adjustments for us and answering questions quicklyThe home is well furnished and well stocked with all your immediate needsThe Home Heart Team was SO incredibly good to me/Such a great family to work withLocation:
Also transfers get you directly to Midway Airport in about 30 minutesPink Line L stop and $12 gets you downtown in 25 minutes to Millennium Parkjust a few minutes walk awayThe house is a few blocks from the L and surrounded by Italian restaurants worth your timeVery easy check in and check out processCleanliness:
The thick bath sheets and bath towels were an appreciated touch of luxuryHouse was clean and everything worked greatAll of the bedrooms were very clean and well appointedThe property is very nice and cleanThe rooms and beds were clean spacious and comfortable with plenty of natural light There are lots of thick thirsty towelsRead more reviewsAmenities & Room:
the kitchen was beautiful and well stocked with everything you would need to for whoever wants to use itHot water showers easy to manage room temperatures andAlthough we did not do any cookingonly a master bath upstairs so guests have to use downstairs bath couldn't find local stations or cable to watch the newsMaster bedroom is terrific with a lovely balcony deck and excellent master bath
3. A perfect home with chic decor
This is the ultimate place to find refuge as you visit this majestic city which comes with stylish decor and very well-lit rooms. It features a fully equipped kitchen with a large granite island, cable TV, a large dining area with an open plan, a hot tub in the main bathroom, free internet, a barbeque grill and bathrooms with necessary amenities. You can also access the following things too, a yacht for hire, a viewing deck, and a patio, an in-house pool table, and pets are also allowed too at a small fee so you don’t have to worry who your pet will stay with while you are away on holiday.
Top guest reviews
Host:
The home is functional Two smoke alarms were not working when we arrivedWe had 7 mother's in this home and all we can say is Love Love and LoveOverall out family had a relaxed vacation and room for 3 generations to spread outThe basement was a big hit with every oneThis home accommodated us very well and perfectly located to everythingLocation:
While the neighborhood is somewhat isolated by the highway and rail line at the north end of Bridgeport and not really within walking distance of attractions we found an excellent restaurant a ver...Thank you Best Girls Night EverWonderful house for a stay in Chicago Within walking distance to the trainThe house is awesomely beautifulNeeded 3 separate contacts to owner to correct low settings but ownerCleanliness:
The bedrooms and bathrooms are really well donebut it only had a dryer which was brokenRead more reviewsAmenities & Room:
The downstairs remotes for cable batteries deadNo one came to fix themWe all enjoyed the spacious well equipped kitchen dining room and living room and the huge basementThere were mouse droppings in the downstairs bathroomThe pool table is broken down and missing pool ball
4. The ultimate holiday spot with the finest city views
If you are looking for the ultimate holiday experience in Chicago, this is the right spot for you. It is equipped with three televisions, a foosball table, a beautiful well-stocked kitchen, fast internet, cable TV, fantastic rooms that come with panoramic views of the city and perfect air conditioning. You can also check out the stunning swimming pool in the same establishment for a leisurely dip as you enjoy Chicago’s fine weather and also the viewing deck that grants you the finest lake views. This apartment will give you the urge to stay an extra day with the array of facilities that come with it. I am sure you will fall in love with this gorgeous property.
1000 S Clark St
5. Gorgeous condo in the heart of the city
Check out this ultra-modern two-bedroom apartment with a lot of space and enough lighting. It features a fully equipped kitchen that comes with stainless steel appliances and Quartz countertop with natural stone backsplash, porcelain floors throughout the living room with oak hardwood flooring in both bedrooms. All the bedrooms come with comfortable full-size beds, luggage racks, and storage space while the bathroom comes with a stand-up shower with sliding glass doors and heating. You’ll also find perfect airconditioning in this condo, cable TV, a balcony with scenic views and bikes for children to cycle if you are coming with a family to stay here.
Top guest reviews
Host:
The owner answered all our questions and requests promptly within hoursand he was very easy to work withGil was very helpful and referred some awesome restaurantsThe owner was very quick to respond any time I sent a messageand we had a wonderful experienceLocation:
5 minutes walk to The L trainApartment is super close to bus line to take you right to Mc Cormick and about 4 blocks away from the train to go into downtown Chicago ApartmentHowever this apt is on the edge of a more questionable area of the neighborhood(Western on the pink line) and thus only 10-15 mins from downtownGreat location close to the LCleanliness:
The apartment was very nicely decorated and meticulously cleanwas super clean and very comfortable and we felt very safe in this neighborhoodThe apartment is very clean and quiet comfortable for 4 people (we had 3)The apartment was clean and beautifulit had everything I needed close to everythingRead more reviewsAmenities & Room:
The only thing we felt it was missing was washer/drier because we did not bring enough clothesPleasant and well lit ground floor apartment
6. Apartment with stylish decor
This beautiful establishment features a two-bedroom suite that caters to all your needs in a spacious layout with fantastic, western decor that gives you a view of the sunset in one of the coolest of cities in America. Each room is uniquely designed with its own stylish accents and convenient amenities to give you the perfect mixture of home and away, You will find the following things once you check in this condo; spacious room with a lot of light, air conditioning, an ultra-modern kitchen with the necessary equipment, cable TV, free internet and free parking.
Top guest reviews
Host:
Quiet and small with a nice kitchentwo nice bedrooms a TV area and a bathroom with good water pressure and plenty of hot water Temperature controlLocation:
A small market and several restaurants were nearbyLocation was great Walking distance to a lot of local eateries and breweries and only a 20 minute (with traffic)and it was easy to get an Uber or lyft when we needed to travelThis Cloud9 APT we rented was greatRead more reviewsAmenities & Room:
We were there in a heatwave and were lucky to have an apt with an AC that worked well
7. Charming holiday accommodation
This gorgeous apartment lies near the Damen Pink Line which is only 25 minutes from the downtown of Chicago. It features rooms with high ceilings, a large living space, two beautifully arranged bedrooms, a fully stocked kitchen, cable TV, air-conditioning and an amazing dining area with an open plan. This place is within a short walk to fantastic Mexican and Italian restaurants so you might want to pop in and try some delicious continental cuisines.
Top guest reviews
Location:
we were also in walking distance of some good mexican restaurantsRead more reviewsCleanliness:
the place was very clean too
8. Condo with superb views
This beautiful condo comes with modern decor, a fully stocked kitchen with stainless steel appliances, a private gym in the building, free internet, heating, cable TV and a great living area with great space and lighting. While here, you’re nearby local restaurants and just a few blocks away from the expansive Grant Park. Delight in the hotel amenities without the hotel formality where this condo caters to your business needs and comes with an ample working area with fast internet to work on your deadlines in case you don’t feel like leaving the room.
Top guest reviews
Read more reviewsHost:
Please let the local manager know that Courtney was extremely helpful professional polite and friendly
Visit the South Loop for an absolutely breathtaking holiday
This scenic destination comes with a ton of attractions which I would urge you to plan and visit. There are a number of places you can visit in and around the Loop, whether its an educational tour or a fun-filled sightseeing vacay. This city will give you the ultimate holiday experience like no other.
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