Condo holiday rentals in West Loop

Quiet and Cozy 2 bedroom condo

Welcome to your tranquil retreat! This thoughtfully designed two-bedroom 1 bath condo blends modern amenities with a welcoming atmosphere, making it an ideal getaway. The living area features contemporary décor and comfortable seating. The kitchen is equipped with stainless steel appliances & granite countertops. Conveniently located near shopping, restaurants & coffee shops O’Hare & Midway airports are approximately a 25 minute drive and Downtown Chicago is approximately a 20 minute drive!

Modern Oasis – Minutes from O’Hare

Relax in simplicity in this peaceful, centrally located garden apartment. Were just 15 minutes from O'Hare Airport, and exciting Rosemont Center, Outlet mall and Casino, 20 minutes from Downtown Chicago, 10 minutes from the fabulous outdoor Oak Brook Mall with tons of shopping, entertainment, and restaurants. This apartment offers everything you need in a serene setting. With easy access to 3 major expressways I-290, I-294 and I-88. It’s in a great quiet neighborhood with friendly neighbors.

Stylish 2nd Floor Flat w/ Parking

Nestled on a pleasant tree-lined street, this former artists' studio is now a beautifully decorated 3 bedroom, 1 bath flat - a perfect combination of historic charm and modern comfort. This 2nd floor private apartment is only steps from the specialty boutiques, antique stores, restaurants, and coffee shops that make Forest Park so charming. We're only an 8 minute walk to the CTA (public transit to Downtown Chicago). A 15 minute walk or 5 minute drive will get you to historic Oak Park, IL.

Apartment in Clarendon Hills.

Newly renovated Suite in multi family home in Clarendon Hills. Main level: fully equipped kitchen/island, dining area, living room & family room with fireplace. Upper level: Bedroom 1 - king size bed, walk in closet​, private bathroom/shower.​ Bedroom 2 - queen bed​, closet.​ Bedroom 3 - size bed​, closet. Living room has a pull-out sofa bed​. Family room with gas fireplace, access to deck/outdoor area.​ Easy access to restaurants, shopping (Oak Brook Mall minutes away), Metra, O’Hare.

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Eco-Friendly, modern, sleek, condo with modern finishes and a sweeping Sky Terrace and resort-like amenities are just steps from Northwestern University, Loyola, and Kellogg and minutes from Chicago. Joy of Evanston features granite countertops in the kitchens, 9 ft ceilings, and designer plank flooring. Enjoy luxury amenities such as a fully equipped fitness center, outdoor pool, BBQ and picnic area and beautiful landscaping. Guests can enjoy the Clark Street Beach & Lighthouse

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 minutes from downtown Chicago and 15 minutes from Midway Airport. Perfectly suited for business travelers or a group trip: two queen beds, a fully-stocked kitchen, a 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!

Lovely condo in the heart of Downtown Oak Park!

The whole group will enjoy easy access to everything from this centrally located place. 2 bedrooms, 2 baths, lots of living space. Open concept kitchen, living, dining, and extra space for work/play space. In-unit laundry. Great outdoor deck, free parking all in the heart of downtown Oak Park with restaurants, theater, street fests, parks, green line/metra for easy access to Chicago. Quiet unit with its own entrance and no shared walls. You will love it here!

OakPark/Public Transport/2 Bedrooms/Sleeps 6/Wi-Fi/Change Room/Laundry/Garage

Stay in a charming 2BR Victorian apartment in the heart of downtown Oak Park! Just a 2-minute walk to the L and Metra for a quick 20-minute ride to Chicago. Walk to shops, restaurants, Target, Trader Joe’s, and Frank Lloyd Wright homes. Enjoy a fully stocked kitchen, Roku TV, fast WiFi, patio seating, and parking for 1 small car. Family-friendly with Pack ’n Play and high chair. No parties—perfect families or workers. Pet-friendly with rules & fee.

Spacious Evanston Duplex - Free Parking

Book your cozy winter getaway! Perfect for families traveling to Chicago for holidays, college visits, or long stays. Pet friendly and only minutes to town. Make yourself at home in our large 3-bedroom,2-full bath duplex Ideal for families or groups, our welcoming abode boasts a large king bedroom, a cozy queen bedroom, and two doubles for a peaceful night's sleep. Message me for direct long-term discounts — winter special rates available.

Pet-Friendly Luxury Penthouse | 3 Kings + Rooftop

Stay Somewhere Unforgettable Discover one of Forest Park's most unique stays. This stunning 3,000 sq. ft. penthouse features 3 king bedrooms, 2.5 baths, rooftop access, spacious gathering areas, and original artwork throughout. Walk to dining, nightlife, coffee shops, and transit, with easy access to Downtown Chicago. Perfect for families, wedding parties, girls' weekends, business travelers, and special celebrations.

Insta-worthy Loft Condo, FREE Parking, Fenced Yard

Enjoy the convenience of free parking and easy access to public transportation. This modern and cozy space features a fully equipped kitchen, high-speed Wi-Fi, and a cozy living room. Discover the charming neighborhood of Oak Park, with unique shops, great restaurants, and historic architecture. With major highways nearby, this 2nd floor condo is the perfect home base for your Chicago adventure.

Picture Perfect 3Bed Steps from Train and FLW

Welcome to your beautiful 3 bedroom home-away-from-home! From the Insta-worthy forest room to the cozy fireplace reading nook to the modern ice crusher in the kitchen, we've put so much thought into this home that we're sure you won't ever want to leave. Welcoming and newly updated, this unit is close to restaurants, shopping, the best of Frank Lloyd Wright, and the train to the city.