Holiday rentals in Chicago River

Modern LOFT Ukrainian Village 2nd floor

Private, Bright 2nd floor Loft with Tall Ceilings with Lots of Light. Creative Decor with Artwork and Artifacts. Relaxing and Cozy. Tree Top View of the Garden. Everything you need for a Long or Short Time Stays. Stocked Kitchenette, Modern Bath, Laundry and Fast WI-FI . Perfect for 1 or 2 for work or play. The Street is Quiet, Conveniently Located just 1 block from Bustling Division Street in Wicker Park, Downtown, the Blueline to all Airports and 1 Mile from the New Salt Shed Music 🎵 Venue

English garden apt. in the heart of Lincoln Park

Welcome to this new, totally furnished apartment in the heart of East Lincoln Park…only a 3 minute walk to the Lincoln Park Zoo! Apartment has been completely renovated with high finishes throughout. Living room boasts a 50” television with Dish TV, internet and a queen sleeper sofa! Gourmet kitchen with granite counter tops with an eat-in bar height counter top. Truly gourmet kitchen! Bedroom with en-suite European styled bathroom. Wall mounted television in the bedroom. In unit laundry.

Style, comfort, and convenience

Enjoy a stay at this centrally located, spacious 1st floor condo. Within a 10-minute Uber ride to West Loop, Downtown, Chinatown, Pilsen, museum campus, and medical district. Public transport is close, with a bus to the museum campus/Soldier Field 1/2 block away. Train a 15 min walk. This 1,050 sq ft condo includes a full dining room and living room. Nearby are Target, CVS, Jewel, Whole Foods, and the "Chicago Fire" filming location. All amenities within a 2-mile radius for your convenience.

Vital Urban: Spa Inspired Retreat

Experience a unique urban spa inspired retreat in Wicker Park, just a 5-minute walk from the Damen Blue Line. Named one of the hippest neighborhoods by Forbes, Wicker Park buzzes with energy, and Vital Urban offers the perfect balance—tucked away in a peaceful spot while keeping you close to all the action. After a day of exploring, unwind in your private steam room, designed to melt away stress, or soak in the oversized jetted tub—your ultimate retreat from the city’s vibrant energy.

Spectacular 2BR Penthouse in the Loop | Roof Deck

This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With over 1,200 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 Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed. The building has a pool and an amazing outdoor rooftop terrace with 360 degree views of the skyline and lake. This is the best location in the city!

Kasa | Explore the Neighborhood-Mag Mile | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Little Italy Historic Restoration Row House

Location, location... fully rehabbed, historic 1884 row house w/2 Queen bedrooms and 2 bathrooms across from Arrigo Park in safe, quaint Little Italy. UIC campus, Rush University Medical Center and Illinois Medical District are blocks away. United Center is 17 minute walk and downtown sightseeing easily accessible by nearby public transportation. Fujitsu heating/AC units for individual comfort. Beautiful professionally maintained gardens outside your door.

Chicago Tropical Condo

Spacious 3 bedroom/ 2 bathroom condo 2 miles from downtown. Perfect for a group of friends or a large family. Free street parking outside. Located in a quiet neighborhood to relax as if you were at home, but still be close to the city for all it has to offer. Biking distance from downtown, the lake, Soldier Field, United Center, Shedd Aquarium, Millenium Park and Navy Pier. Walking distance to dozens of restaurants in Taylor Street &Little Italy.

A Family Rowhouse by UChicago

Our three level rowhouse includes a main floor with an open concept living space and kitchen making it the perfect gathering space. Basement in-law suite with kitchenette allows for max privacy for a large group. Located on University Ave. steps from UChicago and easy access to the lakefront trail and beaches as well as to downtown via Metra or express bus. A short walk to downtown Hyde Park. NOTE: Registered guests only. No parties. Thanks!

Modern 3BR with Private Rooftop & Free Parking

A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.

Sun-Soaked West Loop Penthouse/Private Rooftop/3BA

This Sun Soaked West Loop Penthouse is the perfect home away from home. With it's expertly designed living areas and alluring outdoor spaces, there is nothing this unit doesn't have. It is equipped to be lived in full-time and is owner occupied and maintained as a primary residence for a portion of the year. NOTE: Photos are up-to-date as of 5/5/2024 www.westlooppenthouse. com

The Alton - Designer Flat by Mag Mile & the Lake

A design lover's dream. Spend your next trip (or staycation) in a beautifully remodeled luxury studio in Chicago's Gold Coast neighborhood. This listing is for a private studio in a multiple-unit building. ✔ Safe and vibrant neighborhood. ✔ Steps from Michigan Avenue, luxury shops, and the Lake ✔ Convenient parking options nearby. ✔ Easy self-check-in.