Condo vacation rentals in Chicago

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!

OakPk/PublicTran/2bd/sleep6/WiFi/Chgo/Lndry/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.

Gorgeous Pet-Friendly Penthouse | 2 King + Rooftop

Stay Somewhere Unforgettable Discover one of Forest Park's most unique stays. This stunning penthouse features 2 king bedrooms, 1.5 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.

Just remodeled apartment close to airport and mall

This is just remodeled first floor 1 bedroom apartment that has everything you need for a comfortable stay. Conveniently located 14 min from O'hare airport and 10 min from Woodfield mall that has to offer variety of stores and huge amount of restaurants. All kitchenware for cooking your meals, board games for fun, pool to relax in summer and some snacks to get most out of your stay here.

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.

Spacious Evanston Unit - Walk to Northwestern U

Welcome to my contemporary and spacious garden level unit located on a tree filled, serene residential block in Evanston. Walking distance to Northwestern University, retail areas, trains, golf, and the lovely beaches of Lake Michigan! A Walgreens and a local brewery restaurant are just a few steps away. Plentiful free street parking and free EV chargers one block away.