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2 br, 2 bt, UChicago Coachman's Guesthouse

This 2 bedroom, 2 full bath, stand alone UChicago Coachman's House sleeps 5 comfortably. Less than 1/2 mile to the UChicago main quad. Situated on a quiet residential street. Full kitchen to prepare your own meals and dedicated laundry. Easy access from O'Hare or Midway airports. Less than 2 blocks from the Metra train to downtown, Mccormick Place, Soldier Field, Wintrust Arena, Grant Park and Millenium Park. Walk to Trader Joe's, Walgreens, restaurants, lakefront, stores, museums and more.

Guesthouse | Near public transit and Lake front

A unique 400 sqft loft with bright open concept multipurpose space, large windows, full kitchen, and private access located in the historic Kenwood/Hyde Park area. Public Transportation - 5 minute walk Lakefront - 10 minute walk University of Chicago - 2 miles Museum of Science and Industry - 2.8 miles Mccormick Place 3.4 miles Millennium Park - 6 miles Navy Pier - 6.7 miles Hyde Park restaurants! Perfect for individuals or couples, great access to expressways to get anywhere in the city.

Retro Modern Bungalow | free parking | fire pit

Experience the city in style at Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Live Stylish in Hyde – 2BR Haven

Make yourself at home in this cozy Hyde Park escape. Modern and stylish 2BR/2BA unit in the heart of Hyde Park, perfect for up to 4 guests. Enjoy two comfy queen beds, a fully equipped kitchen, cozy living space with TV and fast Wi-Fi. Each bedroom has its own bathroom, ideal for families or friends. Located on South Shore Drive—steps from Lake Michigan, parks, cafes, and the University of Chicago. Clean, comfortable, and perfect for short or long stays. Your Hyde Park escape awaits!

Cozy Hidden Gem Near Downtown+Train+Dining+Parking

Experience one of the best neighborhoods in Chicago in this Hidden City Gem, 2BR/1bath apartment. Perfect for couples, families, or small groups. Centrally located, just minutes to downtown, CTA/L Pink Line train is one block away, Free WiFi, permit parking, cable, in-unit front load washer/dryer, highways nearby. Explore the vibrant community, art/murals, delicious food, and cultural venues. Book now for a comfortable and memorable stay in the Heart of Chicago Pilsen Neighborhood.

Spacious 1BR Garden Apt & Parking

Welcome to our tranquil garden apartment on a quiet residential street near the university and all Hyde Park attractions. Enjoy morning light through picture windows in the spacious living room and adjacent kitchenette. Breakfast on the patio or garden bench on a sunny morning. Stroll to one of 20+ eateries within four blocks. This is our home, so we are mostly upstairs or nearby if needed. Access is private via back gate just off the parking lot with reserved parking space.

Historic mini mansion!

The whole group will be comfortable in this spacious and unique space. With generously sized rooms and two and a half bathrooms, there’s plenty of space for families or groups. Each room tells a story, with original woodwork that whispers the charm of a bygone era. Explore the original craftsmanship of Chicago reflected in our stunning staircase, the proud centerpiece of the home, inviting you to ascend to the second and third floors where comfort meets character.

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

This will likely be the largest condo you have ever seen. This condo is 5 mins from the University of Chicago and the University of Chicago hospital. You will be a quick 10-15 min uber ride from downtown and 5 mins from beautiful Lake Michigan. We are currently only booking out of town travelers. We are not doing parties or events. I live in the building so if you are trying to have a party I will have it shut down and you will be asked to leave within an hour.

A Family Rowhouse by UChicago

Our three level rowhouse includes a main floor with an open concept living space and kitchen making it the perfect gathering space. Basement in-law suite with kitchenette allows for max privacy for a large group. Located on University Ave. steps from UChicago and easy access to the lakefront trail and beaches as well as to downtown via Metra or express bus. A short walk to downtown Hyde Park. NOTE: Registered guests only. No parties. Thanks!

Modern 3BR with Private Rooftop & Free Parking

A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.

Hyde Park Studio Near UChicago & Lake

Welcome to our cozy Hyde Park studio, perfect for 2 guests! Just minutes from the University of Chicago and the beautiful lakefront, this space offers comfort and convenience in one of Chicago’s most historic neighborhoods. Explore the vibrant 53rd St strip filled with cafes, shops, and local charm. Whether you're here for study, leisure, or a bit of both, enjoy a peaceful stay in the heart of Hyde Park.

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

Sophisticated Roscoe & Halsted duplex w garden. Sleeps 6 - 3 beds in 3 bedrooms + 2.5 baths. Steps from bars & restaurants, 2 blocks from Wrigley Field & Lake Michigan. Perfect for sports enthusiasts, enjoy Boystown, get-aways. In addition to central heat and air conditioning, ceiling fans with remote control in each bedroom.