Holiday rentals in Chicago River

Oldtown Stylish cute studio Near Gold Coast

Welcome to our stylish studio unit nestled in the heart of the city's charming old town area! This cozy space is perfect for solo travelers or couples seeking a comfortable retreat. The studio boasts a spacious bathroom, providing ample room for relaxation after a day of exploring.With its central location, you'll have easy access to the city's vibrant attractions, trendy cafes, and historic landmarks. Our studio unit offers the perfect blend of convenience and comfort for your stay in the city.

Chicago Modern Condo 2BR2BA, Balcony, Free Park

Experience upscale city living with @TheDreamRentals in this stylish 2-bedroom, 2-bath Airbnb located in Chicago’s vibrant Tri-Taylor neighborhood. This modern retreat features sleek interiors, spacious bedrooms with queen beds, a fully equipped gourmet kitchen, and designer finishes throughout. Enjoy high ceilings, large windows, and smart amenities just minutes from downtown, the United Center, and the Illinois Medical District. Perfect for professionals, couples, or small groups seeking comf

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln

Cozy English garden apt (300 sq ft) w/ priv. entrance & free offstreet prking. 4 min walk to Blue Line. Brightly lit / high ceiling. Adjustable Tempupedic memory foam QUEEN bed plus futon in lvng rm. Kitchenette w/ mini-frig, Nespresso & Keurig, toastr ovn, microwv, and waffle maker w/maple syrp. Designer bath. 30+ restaur/bar nearby (see GUIDE BK in LOCATION). Self check-in. Flexible cancel. Early lugg. drop. A space to unwind in -- art-filled and artistic in design, NOT bland or IKEA like!

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond to our house rules.

Spacious Hotel Room in The Loop

Just steps away from the famed shopping on State Street, this boutique hotel is located inside the Nederlander Theater building in the Chicago Loop Theater District. The hotel features on-site dining, state-of-the-art business services and modern guest rooms with free WiFi. Every room at Cambria Hotel Chicago Loop/Theater District provides a 49-inch flat-screen HDTV and a large work space with a desk and ergonomic chair. Select rooms also offer plush lounge seating.

Lovely 1-bedroom serviced apartment near Museums!

Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Long Stay,The Jewels,2bd/2ba,UC 2mi,Pkg,DTWN 15mi

Welcome to ABODE6535: The Jewels Suite. This apartment is named after Chicago's popular grocery store chain and its residents' unique way of saying it. :) This vibrantly curated apartment is designed for comfortable extended stays that may make you consider making Chicago home, or at least make sure you feel at home while you're here. You will be welcomed into a well-appointed space with cozy linens, sparkling clean bathrooms and warm touches at every turn.

Chic retreat near the best of Lakeview & Wrigley

Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

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.

Cozy Little Village Studio

Kick back and unwind in this Cozy Chicago flat. This newly renovated unit is conveniently located in the “little village” community and offers a convenient stay with everything you need to enjoy Chicago. Come stay in a historic red brick building within an authentic Chicago community.

PH w/ Bean & Lake Views, An Elite Stay

For travelers with uncompromising standards, 'The Orion' is an exclusive 3000ft² penthouse offering iconic The Bean & Millennium Park views and access to a private amenity floor. It's a proven elite experience, with a remarkable 9 out of 10 recent guests leaving a 5-star review.