Apartment holiday rentals in Downtown Chicago

Stylish 2-bedroom flat in Vibrant Bucktown.

* Please be aware the city of Chicago is currently renovating its lead pipes. Construction is inevitable and noise. Its a city there will be noise. Hello and welcome to Bucktown! One of Chicago's most popular neighborhoods. Bucktown is centrally located, just a short commute to downtown and surrounded by the best dining and entertainment options Chicago has to offer. We are also half a mile from the expressway and 1 mile away from the Blue Line which directly connects to O'hare airport.

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)

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Luxury 4BR/2.5BA residence featuring 3 private bedrooms and an open-concept bonus room with a queen bed and full-size bunk beds—perfect for upscale families or executive groups. The spa-inspired primary suite offers a soaking tub and rain shower with multiple settings. Enjoy a modern kitchen, stylish living room with a 76” smart TV, and a large covered patio. Located near UIC, West Loop, Chinatown, McCormick Place, the lakefront, and some of Chicago’s best dining and cultural attractions.

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.

Charming Condo near U.C./Loop/McCormick Place

Our spacious 3-bedroom, 2-bathroom condo is designed for comfort and convenience. Perfect for extended stays, it features a dedicated workspace with a desk and office chair, plus an in-unit washer and dryer. Two bedrooms offer cozy queen beds, while the third has a comfortable futon. The master bath is large enough for multiple people to get ready at once, and the fully stocked kitchen is ready for your culinary creations. Enjoy extra privacy in your secluded space within the building.

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.

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

River North 2-Story · Free Parking · Home Theatre

Two-story River North retreat made for families and business travelers. Free onsite parking, a rare find downtown, plus a fully equipped gourmet kitchen, real dining area, and cozy basement home theatre for movie nights. Unwind in comfortable bedrooms and spa-style baths, then step out to River North’s best dining and nightlife. Hotel Godfrey is under 400 feet away, with the Mag Mile, Chicago River cruises, and Millennium Park all minutes from your door.

MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Beautiful views of Chicago ✅ Central Location ✅ Parking garage attached to the building ($15-30 / night - Operated by LAZ) ✅ FAST WIFI ✅ Comfy KING beds ✅ Shared Rooftop Deck w Grills ✅ 1 block from Red "L" subway ✅ Close proximity to Grant Park, Soldier Field, Museums

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)

Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

3D Tour! Designer Condo near Logan Square

Scan QR code in photos for a 3D Tour! What you’ll love: - Totally renovated garden unit, completed in 2021. Everything new. - Upscale furnishings & decor. - Gourmet, fully equipped kitchen w/ new appliances, coffee maker and spices. - Remote work station w/ super fast Wi-Fi (600mb). - Serta queen mattress in master. - Bunk beds w/ full and twin sized memory foam mattresses. - Heat & A/C.

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.