Condo holiday rentals in Illinois

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Escape into this spacious, Chicago Penthouse! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Private, spacious roof deck viewing the entire Chicago skyline! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out - Designated parking spot! - Steps away from blue line Damen station (800 feet)

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Sunny Top-Floor Uptown Condo Near Lake & Red Line

Bright top-floor Chicago condo with fast WiFi, dedicated workspace, and easy access to Montrose Beach and the CTA. Perfect for remote workers, couples, and travelers looking to experience Chicago like a local. Enjoy a sunny living room, fully equipped kitchen and dining room, spacious primary bedroom, and serene sunroom with a full-size bed. Just steps from the lakefront and a 6-minute walk to the 24/7 Wilson Red Line. Over 1,000 sq. ft. of comfortable living space in historic Uptown.

Can't Beat This 2min Walk to Wrigley!

My home is a half block from Wrigley Field. You can be to the ballpark in 2 minutes (or Murphy's)! Enjoy your pregame afternoon feeling the buzz of the neighborhood from the private deck. Room for 6 to sleep comfortably in a Queen, 1 Twin plus a Twin over Full Bunk Bed and a Murphy Bed. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea! I have extensive information for you - let's chat!

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Beautiful Condo - King Bed - Free Waffle Breakfast

Welcome to the Gem of Geneva! This peaceful home is the perfect place to rest! It's elegant, clean, and fully-equipped! It's perfect as a stop over on a work trip, a getaway with your family/partner, or a long-term stay! Come kick off your shoes after a long day, take a hot bath in the soaking tub, and then enjoy some fresh warm waffles in the morning with our complimentary waffle station. Feel free to reach out! I am happy to host you and answer any questions you have!

Pelican's Perch

Looking for a cozy and comfortable getaway? Pelican's Perch is nestled in the bluffs along the confluence of the Illinois and Mississippi rivers. Watch beautiful sunsets, bald eagles or river barges right from your own covered deck. Enjoy wineries, restaurants, bars & shopping -- all within walking distance. This beautifully decorated 3-bedroom condo is ideal for families, couples, business travelers or girls' or guys' weekends.

Chicago Oasis | Spa Bath, Patio & Fireplace

Experience the best of Chicago from this centrally located retreat just minutes from Downtown, top restaurants, shopping, and iconic attractions. Relax in a spa bathroom with a jetted tub and rain shower, cozy up by the fireplace, and enjoy a fully equipped kitchen. A king bedroom and queen Murphy bed comfortably accommodate up to 4 guests. Finish your evenings on the private patio gathered around the fire table.

Modern Izakaya Studio in Wicker Park

The Izakaya Studio is a sleek, design-forward space in the heart of Wicker Park, with a secret whisky room inside. Inspired by the intimate atmosphere of a Japanese izakaya: warm, curated, a little unexpected. The kind of place where you settle in, pour something good, and stop thinking about your plans for a while. Spacious for a studio, and comfortable enough for a longer stay in Chicago.

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.

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 on summer so you get most out of your stay here.

Lincoln Square Gem!

Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. We live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!