Holiday rentals in Summit

Treetop Vista, Space+Parking by downtown Chicago

2024 Historic Preservation Award Winner! Airy & bright top floor of a two-flat w/style & A+ location! 2024 gut-rehab. King bed! W/D! 20 min. to dwntwn Chicago + steps to FLW Home. Walk to dining & train. Must climb stairs to enter. 2 bdrms & 1 bath w/tub + shower combo. Open living/dining/kitchen/sunroom. Wow kitchen w/huge island. Primary w/king + deep closet. 2nd bdrm w/built-in bunk beds + desk + balcony. Private entry & deck. Share fenced yard. Driveway parking. Downstairs apt. not included.

1920s fully updated unique open artist loft space

True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

Contemporary NEW Entire Suite Berwyn/Riverside

Welcome to your private oasis! This beautifully NEW appointed 1 bd unit offers the perfect blend of modern convenience and contemporary style. Whether you’re here for a weekend getaway or an extended stay, this contemporary retreat is your perfect home base. Explore the vibrant attractions of Berwyn or the excitement of Chicago, just a short trip away. Book today to secure your stay and experience the blend of comfort and style in this chic contemporary gem. We look forward to hosting you!

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

Rockin' 2Bed steps to shops/food/train

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

Retro Modern Bungalow | fire pit | free parking

Experience the city in style at our 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.

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

Paradise in the Park

Welcome to our home. Enjoy the park connected to our backyard, featuring new playgrounds, soccer fields, and a walking trail. Our well-appointed kitchen is ideal for preparing meals together. The living areas provide plenty of space for bonding, and our extra comfy beds will ensure your maximum relaxation. We are located 20 minutes from the heart of Chicago, and about 10 minutes from Midway Airport, several hospitals, and the famous Brookfield Zoo. We can't wait to host you!

2BR Chicago Escape | 20 min DT, Parking, Laundry

Welcome to our stylish 2 bedroom condo - thoughtfully designed to provide an authentic Windy City experience! Located just 20 mins from downtown Chicago and 15 mins from Midway Airport. Perfectly suited for business travelers or a group trip: two queen beds, fully-stocked kitchen, Keurig coffee maker, a dedicated workdesk, and several board games for your enjoyment. Attached laundry facilities and free parking. Book now for an authentic urban experience!

Chicago Buddha's Abode

Welcome to our humble abode in Berwyn! Built in 1899, known for its true Victorian charm, we're opening our first floor(unit 1) only to travelers while we temporarily relocate to North Carolina. This is not just a place to stay—it’s a home with soul, thoughtfully furnished and full of warmth. Our living space offers a tranquil vibe and makes you feel right at home. Enjoy your coffee with bird chirps by the yoga room overseeing the backyard!

2BR Apartment Near Chicago

New Beautifuly Renovated Modern 2BR Apartment sitting right aside Hanover Park with Playground, Large Field, Swings, & Basketball Court. In a Peaceful neighborhood near the downtown Chicago area. 10 minute drive from Midway Airport and a 20 minute drive to lakeshore drive, Millenium Park, beaches, restaurants, museums, and more. You'll be pleased and delighted to stay here among its Cozy living room, Beautiful Kitchen and Serene Rooms!

Cozy Home in Brookfield

Discover tranquility just minutes from the busy city life! Nestled in the heart of Brookfield, IL, our charming home offers the perfect blend of suburban serenity and urban convenience. Just an 8-minute walk from the train station, you'll find easy access to downtown Chicago while enjoying the peaceful atmosphere of our neighborhood. Pets are allowed, but no exotic pets and no cats or dogs with a bite history.