Holiday rentals in Chicago

City-Accessible Basement Retreat

Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

All-glass gem by Chicago architect Harry Weese

Designed by renowned Chicago architect Harry Weese, Swissotel Chicago is an award-winning luxury hotel overlooking the Chicago River and Lake Michigan, and just steps from the Magnificent Mile. The distinctive 4-diamond, all-glass hotel offers spectacular wrap-around views from Navy Pier to Millennium Park, 662 guest rooms and suites, five premier ballrooms, state-of-the-art penthouse fitness center, and spotless European-style service. Pet Friendly, $50USD/night, $250 refundable deposit.

Bright & Spacious| Free Parking |Trendy Bridgeport

Step inside and be greeted by an open-concept space bathed in natural light. High ceilings, hardwood floors perfectly blend vintage charm with modern elegance. The living area invites you to unwind after a day of exploring our vibrant city. Relax on the sofa, watch your favorite shows on our large flat-screen TV, or indulge in book in the cozy seating nook. Whether you're a solo traveler, couple, or friend group looking for an unforgettable adventure, this is the ultimate urban retreat.

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

NEW Jade Haven in Berwyn/Riverside

Step into Jade Haven, where tranquility meets modern elegance. This serene one-bedroom, one-bath suite offers a peaceful retreat, inspired by the calming essence of jade. The space features a sleek, airy design with thoughtful touches to make you feel right at home. Fully equipped kitchen, cozy living area, the bedroom invites restful nights, while the spa-like bathroom offers a moment of quiet indulgence. Perfect for a restful getaway or a productive stay.

Spectacular Pilsen Studio for 2!

This chic studio in the heart of Pilsen is the perfect space to kick back and relax during your visit to the Windy City! The vibrant neighborhood always has something to offer to any type of traveler, and it's a quick trip to see most of the iconic Chicago sights. Easily walk to historic Thalia Hall, or drive to the Loop in just 5 minutes! You'll love the thoughtful touches and modern decor in the apartment, as well as the bright and welcoming main space.

Andersonville Luxe Pool Escape

Welcome to the only chic, two-story pool house just steps from the heart of Andersonville. Enjoy a full kitchen, queen bed, spa-style bath, washer/dryer, and high-speed Wi-Fi. Outside, unwind in your private heated pool and spa in a tranquil, secure setting shared with the owner. Perfectly located near vibrant shops, dining, and a pleasant walk to the beach, this stylish retreat blends comfort, privacy, and convenience for the ideal city escape.

Sonder Onterie | King Studio Apartment

Welcome to Onterie, where modern style meets an unbeatable location in the heart of Chicago's Magnificent Mile. You'll have world-class shopping and award-winning dining at your fingertips. Each apartment includes a fully equipped kitchen, in-suite laundry, and a Roku to stream your favorite shows. Unwind in the outdoor courtyard, or find focus in our co-working space. Onterie offers the perfect blend of city and lakeside living.

Lincoln Park Haven: Balcony, Walk to Whole Foods

Your perfect base in Chicago awaits at 'The Elm', a brand-new 2BR apartment in Lincoln Park. Enjoy stunning views of Chicago's skyline and Lake, complemented by modern amenities including a rooftop pool and gym. This great place offers easy city access via the Red Line train station, with Whole Foods across the street and charming cafes and stores nearby.