Holiday rentals in Chicago River

CUTE, PRIVATE & QUITE STUDIO 1BD/1BA Wicker Park!!

Grateful location, Wicker Park has everything nearby based on walkability to explore! Many boutique shops, a number of coffee shops and locally own restaurants and bars. A 2 minute walk to CTA Blue Line subway excess to downtown Chicago, Lake, Museums or to O’Hare Airport and Midway Airport. SPACE: Entrance to building, very welcoming. Stairs and hall very clean, have laundry area coin washers and dryer (if needed). Studio very clean, professionally, to ensure the wellness to our guest's

Andersonville Luxury Pool Escape

Welcome to the only chic, two-story pool house just steps from the heart of Andersonville. Enjoy a full kitchen, queen bed, spa-style bath, washer/dryer, and high-speed Wi-Fi. Outside, unwind in your private heated pool and spa in a tranquil, secure setting shared with the owner. Perfectly located near vibrant shops, dining, and a pleasant walk to the beach, this stylish retreat blends comfort, privacy, and convenience for the ideal city escape. The pool and spa are heated heated through 12/31.

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 | Views from your Private Balcony | 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.

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.

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!

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

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.

Elegant Suite in Gold Coast

Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, this generous one-bedroom apartment is perfectly situated in the middle of the action for your Chicago adventure. ***Please note that from March until the end of May 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours***

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

Sophisticated Roscoe & Halsted duplex w garden. Sleeps 6 - 3 beds in 3 bedrooms + 2.5 baths. Steps from bars & restaurants, 2 blocks from Wrigley Field & Lake Michigan. Perfect for sports enthusiasts, enjoy Boystown, get-aways. In addition to central heat and air conditioning, ceiling fans with remote control in each bedroom.

Fantastic West Loop 2 bedroom

Beautifully renovated apartment in Chicago’s best neighborhood for fun and food in Landmark building next to public transportation. Two bedrooms with two bathrooms and a chef’s kitchen. Everything you and your friends or family need for an awesome weekend in one of the best cities in the world.