Holiday rentals in Blue Island

Relax. Relate, Release in our Bungalow

Relax in our spacious Bungalow. Relate in the essence of another Chicago gem. Release your inner thoughts during your stay. Hardwood floors set this space as you travel the first level. Traveling to the second level you are met with carpet for a short while. This home is great for family, couples, individuals, short and long stays. Close to major highways, bus transportation and walk/bike paths. Very quiet tree-lined neighborhood. About 20mins to downtown and close to south suburbs of Chicago.

Lovely Ranch with Suburban Feel!

Relaxation, peacefulness and space is what you get when you stay at our Lovely Ranch Oasis in the city which is on a beautiful quiet block that has very suburban feel. After exploring all that the city has to offer, visiting all of the popular spots, touring, having fun, shopping, etc, this is the perfect place to come back to, unwind and end your night. The home is great for those who are vacationing or are here for business and really want and appreciate the feeling of home away from home!

The Ashlin House.

Stay at our family-friendly home on a quiet, cobblestone street on vacation or business. We've recently repainted the exterior and painted the master BR. Walking distance to quaint Downtown Whiting , Lake Michigan, Whihala Beach & Lakefront trails. The Horseshoe Casino, Wolf Lake & Pavilion, Hammond Sportsplex, Calumet College, PNW, IUN, U of Chicago, BP, & golf courses are a short drive. See Chicago's Skyline at Lakefront Park. Chicago's attractions & Hard Rock Casino are < 30 mins away.

Cozy, Artsy Gem in Historic Pullman

Our home is a great getaway from the hustle and bustle of downtown. The interior, tastefully rehabbed, showcases art from local artists. The neighborhood has the same charm of the late 1800s when the house was built, and is within walking distance of the Visitor Center, Exhibition Center, Pullman Club Coffee Shop, and the National A. Philip Randolph Pullman Porter Museum, which is currently under construction. My husband and I live directly across the street makes us accessible to guests.

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Beverly Basement Guest Suite Feb 2026

Great location. Recently Rehabbed in the Beverly Neighborhood. Space: This is a new guest suite in the basement of my home. The suite features a full kitchen with high-quality appliances. It includes a large bathroom, a bedroom with a new queen-size mattress, and an in-suite washer and dryer. The suite offers a peaceful and comfortable place to stay. A 2-block walk will get you to the commuter train, Subway sandwiches, CVS Pharmacy, award-winning barbecue, and Starbucks.

Comfortable and Cozy Apartment

Enjoy this simple and cozy apartment! Located just a few blocks from stores like Walgreens, Aldi, Target, Laundromat and various restaurants. Its conveniently located just a 10 minute walk from the orange line cta train station. Disfrutá de la sencillez de este alojamiento tranquilo y céntrico. Ubicada a dos minutos de tiendas como target, Walgreens, Aldi, Lavandería y restaurantes . Estamos a 10 minutos del aeropuerto midway y 15 minutos del centro de Chicago.

Beverly Cottage Loft

Whether you're looking to stay near family or be close to downtown, our place has it all. This tranquil cottage is located in Beverly which is one of the safest neighborhoods in the city of Chicago. Downtown is a quick 20 minute drive and there are also many restaurants and bars in this area. This cottage has been renovated and have all the essentials you need. All you need to do is unpack your bags and enjoy your vacation. The space is modern, clean, and cozy.

Warm and comfortable inviting Suburban home !

160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

Agave Escape | 6 BR/2BA | 20 Min to Downtown

Agave Escape is a modern, spacious home in a great neighborhood, just 20 minutes from downtown Chicago. Features 6 bedrooms, 2 full baths, and flexible sleeping for families, groups, or work trips. Open living and dining area, fully equipped kitchen with bar seating, fast Wi-Fi, and smart TVs. One bath includes a deep soaking tub. Laundry room accessible to guests. Clean, comfortable, and easy access to highways, dining, and essentials.

Charming Unique 2 Bdrm Apartment in Victorian Home

My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.

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.