Holiday rentals in Chicago River

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

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.

Panoramic 2BR Penthouse in the Sky | Roof Deck

[NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2nd rooftop remains open and available for guests to use.] This sunny top floor penthouse is in a perfect location with panoramic lakefront and city views in multiple directions. With over 1,300 square feet of space, 13+ foot tall ceilings and oversized windows, this spacious penthouse is a true escape in the sky in the heart of downtown Chicago. It's a two bedroom, two bathroom apartmen

Sunny full floor (Sleeps 4+ guests)

A whole floor to yourself — the floor is entirely/ exclusively yours! Full floor finished basement w/ light from glass sliding doors, 1.5 private bedrooms, and 2 desks. Spic & span - steamed cleaned after every guest! New memory foam regular queen size bed w/ 2 more queen size airbeds (per request). 7 mins by car to downtown or 2 blocks to train station/ bus stop that both go into downtown. Street level parking available. Masks are optional, not required. Chicago Registration #: R21000069179

Upscale High-Rise Apt · Rooftop Pool + Views

Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants - Paid parking nearby Unit Highlights: - Stunning views of the city - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modernly designed interior

Cozy Beauty Sleeps 5 - 10 Min to Downtown PacMan

Luxurious 550 sqft 1BR 1BA located 10 min from Downtown! Stand up shower, games for adults & kids, cozy bedroom 2 Smart TVs, free wifi (600 mpbs speed) Grill + Patio Chairs Sleeps 4 comfortably, 1 full bed, 1 queen sleeper sofa, 1 air mattress Street parking can be very difficult!!! - permits provided Walking distance from famous 26th street, plenty of restaurants 3 miles from Little Italy and Chinatown 15 min drive from Millenium Park and Soldier Field Great for professionals and travelers.

Fulton Market Masterpiece 2BR/2BA (+garage spot)

Welcome to this West Loop/Fulton Market Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Randolph St. - Close to every popular attraction that makes Chicago so great - Attached, garage parking spot! - Luxurious interior design - Tranquil patio off kitchen - Fast WiFi - Very comfortable sleeping! - State-of-the-art kitchen - Beautiful, primary en-suite! - 10 minute walk from green line (CTA L) We look forward to hosting you!

ChicagoRiver Double Room

Nicely decorated Private (10x11 sq ft) Room w/designated work station, well-lit, *shared common bathroom* (other guests may be in the premises). This is NOT a full condo rental; just 1 room. Quiet & clean, 2 miles from downtown, walking distance to dozens of restaurants in Taylor Street & Little Italy. Perfect location in a quiet neighborhood, but still close to the city to enjoy food& music festivals, free concerts in Grand Park, Museums, Broadway shows, etc

Egyptian Room - Free Parking, 1 block to CTA

Comfortable lower level bedroom with a pillow top king bed, granite topped desk, and smart tv makes this room a super cozy retreat, You will have full access to the kitchen cooking and free Keurig coffee. You have a private mini fridge in your room for food storage. There are multiple common areas on the 1st, 2nd, and 3rd floors including Dining, Living, TV, and Recreation rooms. Easy unmetered street parking is readily available for those coming by car.

Downtown Guild #4 | Mag Mile, Gold Coast

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Welcome to one of the best locations in Chicago. Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - Steps away from the John Hancock - Gym in the Basement - Amazing location w/ many shops & restaurants nearby - Fast WIFI - KING bed - Charming, vintage Chicago building Please read our FAQs to answer any questions before booking.

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.