Holiday rentals in South Loop, Chicago

5 out of 5 average rating, 4 reviews

The South Loop Suite

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.

4.8 out of 5 average rating, 299 reviews

Kasa | Studio, Walk to Grant Park | South Loop

It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

Guest suite in South Loop

4.88 out of 5 average rating, 8 reviews

Hidden Gem in South Loop

Welcome to your hidden gem Airbnb efficiency, where comfort meets convenience in an unbeatable location! This cozy retreat features a private entrance, ensuring your peace and privacy with a fully equipped kitchen. Located just steps away from local attractions, cafes, and shops, everything you need right at your fingertips. Whether you’re strolling through the city or attending an event at Soldier Field or McCormick Place, this spot is a perfect base for your adventures. Parking $20/day

4.75 out of 5 average rating, 326 reviews

Flat in Pilsen

Bright & Spacious| Free Parking |Trendy Bridgeport

Step inside and be greeted by an open-concept space bathed in natural light. High ceilings, hardwood floors perfectly blend vintage charm with modern elegance. The living area invites you to unwind after a day of exploring our vibrant city. Relax on the sofa, watch your favorite shows on our large flat-screen TV, or indulge in book in the cozy seating nook. Whether you're a solo traveler, couple, or friend group looking for an unforgettable adventure, this is the ultimate urban retreat.

Top guest favourite

Flat in Little Village

5 out of 5 average rating, 11 reviews

2B Midcentury Artist Loft w King Bed

Welcome to Casa D'Mi Amá, this vibrant mid-century loft style apartment is centrally located in Little Village, one of the most vibrant Mexican-American communities and thriving shopping district in Chicago. Our community is known for its colorful murals and hundreds of Latinx-owned businesses and restaurants. We are just 4 mile away from downtown & Midway airport, three miles away from Pilsen & UIC, with public transportation right outside your door making it easy to plan your visit.

4.82 out of 5 average rating, 22 reviews

Flat in Pilsen

Garden Apartment in Historic Pilsen Arts Area

This private garden unit is ideally located and well-equipped with everything you need for a comfortable homebase on your Chicago adventure. Come to Pilsen and experience one of Chicago’s most vibrant neighborhoods. With dozens of unique shops to explore, delightful coffee shops, Pilsen is a beating heart of arts and culture. Peruse charming streets filled with distinctive and historic architecture, admire beautiful street murals, and try one of Pilsen's many delicious taquerias.

5 out of 5 average rating, 9 reviews

South Loop | Rooftop With In & Out Parking | 1

Enjoy a stylish experience at this centrally-located place ✨. Stunning 1,000 square foot modern two-bedroom, two-bathroom unit is perfect for corporate travelers and/or families looking for a stylish escape in downtown Chicago 🌆. 🔥 Rooftop Patio W/ BBQ 🏊‍♂️ Rooftop Pool 🚗 Free In/Out Parking - 5 Mins Walk To Garage 🛏️ 2 Bedrooms | 2 Bathrooms 🛌 2 Queen Beds 🛌 1 Inflatable Airbed 👶 Portable Crib (For Mini Travel Companion) 🎬 Netflix, Hulu, Disney+ & Prime Included

4.67 out of 5 average rating, 311 reviews

Sentral Premium 2BR Apt South Loop Chicago

Experience a lifestyle where everything you need is right at your fingertips in the vibrant heart of Downtown Chicago. Explore the area effortlessly: ✔ Breathtaking views of Lake Michigan and the Chicago skyline ✔ Close to major business hubs and the Loop District ✔ Enjoy a walk along the scenic Lakefront Trail ✔ A lively array of world-class museums, gourmet restaurants, and iconic architecture ✔ Quick access to Millennium Park, the Art Institute of Chicago, and Grant Park

4.78 out of 5 average rating, 144 reviews

McCormick Place Studio/parking/sleeps up to 4

• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security officers in the building • City view • Queen size bed + Queen size air mattress 2 extra guests • Comfortable stay for up to 4 guests at a time • Access to the Gym • Dedicated Internet • 4K smart HDTV(Netflix and Roku) • Fully equipped & stocked kitchen with complimentary Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day

4.99 out of 5 average rating, 108 reviews

Loft in South Side

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.

4.88 out of 5 average rating, 243 reviews

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!

4.89 out of 5 average rating, 166 reviews

Lovely 1-bedroom serviced apartment near Museums!

Holiday rentals for every style

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Popular amenities for South Loop, Chicago holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near South Loop, Chicago's top sights

Millennium Park213 locals recommend

Shedd Aquarium122 locals recommend

The Field Museum95 locals recommend

Other great holiday rentals in South Loop, Chicago

Private room in Bridgeport

5 out of 5 average rating, 3 reviews

Room w/ Private Bath | Chicago

MarkRating, 5 stars6 days ago

Daniel was a fantastic host! He made me so comfortable in his home and yet, I had all the privacy I could want. He described the area in great detail and offered lots of good suggestions on where to go for different meals. His place was exactly as described in his listing and the photos were an exact match. Daniel was a really friendly, helpful guy and I would stay at his place again any time! Thanks, Daniel!

4.77 out of 5 average rating, 121 reviews

McCormick Place Studio/parking/sleeps up to 4

CastwellRating, 5 stars1 week ago

Hands down one of my favorite places to stay in Chicago! The large windows and natural light are stunning the kitchen was great and the bathroom has counter top space. Milan is also a great communicator, proactive and responsive. Will stay again!

4.93 out of 5 average rating, 182 reviews

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

StaceyRating, 5 stars3 weeks ago

Our stay was great. The place looked just like the pictures, super close to the train and easy to get around. Very large living room and table to accommodate a family meal. Both bedrooms were large with very sunny exposures. When sitting in the living room you can see and hear the train, however it the bedrooms it was no problem. They also did provide ear plugs if you are a particularly light sleeper. Everything was great. The directions for entry and departure seemed a bit daunting in print but proved easy to execute once you were on the property.

Private room in Little Italy

4.78 out of 5 average rating, 79 reviews

Beautiful Private Room 5 min to the City

IngridRating, 5 stars2 weeks ago

Super close to UIC, located in a quiet and safe neighborhood. It’s also not far from downtown Chicago. The apartment has five rooms, with a toilet on the first floor and a full bathroom on the second floor. It can get a bit crowded on weekends, which might make the bathrooms busier, but in my experience, they’ve remained clean despite being shared. That said, cleanliness may vary depending on the tenants. Also, the walls are a bit thin, so noise from the first floor can sometimes be heard upstairs. However, people generally keep quiet after 11 p.m.

Shared hotel room in River North

4.75 out of 5 average rating, 24 reviews

Convenient Stay In The Heart of River North

AveryRating, 5 stars2 weeks ago

Great place to stay and very nice lounge/ lobby area. Nice that there are more private bathrooms in the basement.