Holiday rentals in Chicago River

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!

Evanston 2BR 2Bth 1 Blk to Beach

With its older charm, modern comforts, and unbeatable proximity to the beach, this 2-bedroom, 2-bath unit offers an ideal getaway. Only 1 block from beautiful Lake Michigan and South Blvd Beach, you will love our spacious, sunny apt. Whether you're staying for a short visit or a lengthy one, you'll feel the comfort of home on a tree-lined street. The unit has hardwood floors throughout, comfortable bedrooms, a fully stocked kitchen, dining room, and a sunroom looking out on the backyard patio.

Deluxe King Room · Juliette Balcony · Sono B&B

You’ll be charmed by this private guest room inside The Sono Chicago Bed and Breakfast, a newly built boutique B&B in the heart of Chicago’s historic Old Town. This listing is for one private king room with a Juliette balcony within a shared bed and breakfast. Guests enjoy their own bedroom and ensuite space. Complimentary breakfast is included each morning. We’re located on a quiet, tree-lined street and offer cozy accommodations, warm hospitality, and a welcoming sense of community.

Zen in La Grange Park

Relax. Recharge. Explore. Welcome to Zen, your peaceful retreat in beautiful La Grange Park. This charming 2-bedroom ranch offers the perfect blend of comfort and convenience with spacious living areas, a fully fenced backyard, and an attached 2-car garage — ideal for families, friends, or extended stays. Nestled in a quiet neighborhood, you’ll enjoy a relaxing atmosphere while being just minutes from nearby trains and bus stations that provide easy access to Downtown Chicago.

DT Oak Park Luxe|3BR 2BA+Yard|15 min to Chicago

Welcome! Location location location! Relax in this newly renovated 3-bedroom home in the heart of the historic district. Steps from the Frank Lloyd Wright Home and Studio, Hemingway Birthplace Museum, shops, dining, and easy transit to downtown Chicago. Stylish, spotless, and family-friendly — the perfect blend of comfort and charm. No parties, events, gatherings, weapons, dangerous items or disruptive behavior allowed. Every adult must be on the reservation. No exceptions.

Large private room w/ shared bathroom in Boystown!

Located in the middle of the vibrant Boystown community, we are located close to many bars and restaurants, a 10 minute walk to Wrigley Field, and close to make public transit spots to get anywhere. This Bed and Breakfast offers a continental breakfast each morning, smart tvs in each room and free wifi. Parking permits for the surrounding area. Free bag drop off Room service and Cubs Game and Concert Day Specials provided to our guest next door at Big Gay Sal's

Arlo Chicago

Step into the city king room where inspiring views of downtown and a spacious cozy king bed invite you to relax in style. Enjoy smart amenities like a Nespresso coffee machine, a 55 inch flat screen TV, a smart fridge and a work desk. Contemporary luxury design and thoughtful details like a hand held steamer hair dryer and laptop sized safe make this a perfect home base whether you are exploring the city or enjoying a quiet night in.

Rosemont 4BD2BA house with Pool

Enjoy a recently updated home just blocks from the Rosemont Entertainment District, casino and Convention Center, and 3 miles from O'Hare airport. Nestled in a quiet, safe neighborhood, it's central to everything. Relax in the private in-ground pool or head to the basement for an arcade game (100+ games) and board games. Two smart TVs let you stream your favorites. Perfect for both relaxation and entertainment!

Spacious Oak Park 4bd/3.5ba and Parking

Unwind in our classic 4 bedroom, single-family home in Oak Park. It’s perfect for families or groups, offering you a fully equipped gourmet kitchen, 2 living spaces, 3.5 bathrooms, 4 dedicated work spaces, a backyard oasis and parking. With its historic charm, proximity to Frank Lloyd Wright's architecture, Columbus Park and easy access to the expressway, it's central for exploring Oak Park's cultural gems.

Close to Navy Pier + Restaurant. Bar. Gym.

Tucked just off the Magnificent Mile, Hotel Saint Clair gives you front-row access to Chicago’s must-sees—think Navy Pier, Millennium Park, and late-night eats around the corner. Sip your morning coffee, grab your camera, and hit the lakefront in minutes. The rooms are pet-friendly, WiFi’s on the house, and everything you want to see is walkable. It’s your laid-back launchpad for big city adventures.

Luxury Home - Pool Tbl/Bar/Patio

This unique place has a style all its own. Fully remodelled to wow you and your guest! Cozy, yet spacious environment for you and your friends to rest, cook, play pool by the bar or sit outside in the patio with a wood fire! You will be extremely close to downtown Chicago, O’Hare airport, Wrigley Field, many shopping attractions all while being in a safe neighborhood. Easy self checkin process!

A polished, modern affair on iconic Michigan Ave.

Experience an upgraded stay at Le Méridien Essex Chicago, located on Michigan Ave in the city's heart. Our luxury hotel, surrounded by iconic attractions, offers modern rooms with stunning views of Grant Park, Lake Michigan, Buckingham Fountain, and the Museum Campus. We're committed to making your stay in the Loop unforgettable.