Holiday houses in 31st Street Harbor

Sunny Penthouse - Oakwood Beach

Gorgeous top-floor 2-bedroom, 2-bathroom condo in the heart of Bronzeville! With high ceilings and tons of natural light. The fully equipped kitchen has everything you need to cook a delicious meal, or you can enjoy one of the many great dining options nearby. 🌊Take a 15-minute walk to the lakefront and Oakwood Beach. Centrally located near: • Downtown Chicago • Soldier Field & Guaranteed Rate Field • Field Museum & Art Institute • Chinatown, Hyde Park & Pilsen • And much more!

2 BR Apt, close to McCormick, IIT, free parking

2 bedroom 1 bath entire basement unit, separate entrance. 1 queen size bed, 1 full size bed and 1 sofa bed. Located at Historical Douglas Area, Chicago landmark . Close to subway station, bus stop , IIT, loop, museums campus, McCormick Place (25 min walk, or 10 min bus, or Uber<$10), white socks stadium. Area is quiet and safe, near restaurants and super markets. Free street parking. Roof top patio with downtown view . Central heating and cooling, 55 in Roku TV Washer and dryer in unit.

La Casita Norte

Modern Bronzeville 1-Bedroom Apartment in quiet centrally-located neighborhood close to McCormick Place, Wintrust Arena, and White Sox Park, IIT, and 31st Street Beach. Sleeps 4 with a full bed and queen living room sofa sleeper. Comfortable dedicated workspace with reliable Wi-Fi connection and morning coffee. Huge bath w/ separate shower and endless hot water, wet bar, living room, washer/dryer. Fitness room with a Bowflex machine, treadmill, Pilates reformer, yoga mats, trampoline.

West Loop Urban Chic Coach House

Welcome to this historic neighborhood in Chicago, a cultural tapestry, rich in history and bursting with energy. Enjoy strolling along the streets lined with historic buildings, savor diverse culinary delights. Bronzeville is not just a place to stay; it is a community experience Enjoy, this one-bedroom, full bathroom historic coach house with a full kitchen, smart TV, and dedicated living space. Unwind in comfort with an in-unit washer/dryer. Plenty of street parking available.

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!

Peaceful Hyde Park Studio Near UofChi & Nightlife

Stay in the heart of Hyde Park! This cozy 400 sq. ft. studio features a queen bed, 65" Roku TV, full kitchen, and private bath. Walk to the University of Chicago, the Museum of Science & Industry, and 53rd Street’s cafés, shops, and restaurants. Easy access to Metra, CTA buses, and the lakefront make exploring Chicago simple and convenient. Perfect for solo travelers, couples, or weekend getaways seeking comfort and style in a vibrant, historic neighborhood.

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.

3BD | 2 Ensuites | Sleeps 8| Near Sox & McCormick

Welcome to The Bronzeville House — proudly managed by Dwell Well Here. This spacious 3-bedroom, 3-bathroom row home sits in the heart of one of Chicago's most storied neighborhoods. Two private ensuites upstairs, a bed on every level, and an entire home to yourself. Minutes from Guaranteed Rate Field, McCormick Place, Hyde Park, and the lakefront. Everything Chicago has to offer, anchored in the neighborhood that helped build it. 🏡✨

LIVN West Loop Chicago Queen Studio Apartment

Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.

Chicago's Bronzeville Haven

Kick back and relax in this calm, stylish space. Located in the historic Bronzeville community near downtown Chicago. Walking distance to Lake Michigan, McCormick Place, Soldier Field, White Sox Park, Wintrust Arena, museums and public transportation. Quiet neighborhood with plenty of street parking. Walking distance to grocery stores, fast food restaurants and fine dining!

The Modern Woodlawn 2 Bed 2 Bath

Enjoy a stylish experience at this centrally-located place. Minutes from University of Chicago, the upcoming Obama Presidential Library, Golfing at the South Shore Country Club, Lake Michigan, Public Transportation and Downtown Chicago. There is an ALDI grocery store around the corner. Jewels Grocery Store is a few minutes drive by car. Free Street Parking.

Chicago Living: Your Home Away From Home

Historic Landmark Frank Lloyd Wright Townhouse built in 1894. Great Location! Newly renovated private living quarters with separate entrance. This historic townhouse has the distinction of being the only townhouse designed by famed architect Frank Lloyd Wright that was ever built.