Waterfront holiday rentals in Chicago Loop

3 Bed 3 Bath Lakefront Retreat, Parking Included

From the moment you step into the living room of my lakefront home, your breath will be taken away by the incredible scenery outside. Let the gentle sounds of the lake relax you and clear your mind during your tranquil stay. The interior is just as stunning with professionally designed decor, completely new appliances and thoughtfully curated amenities. You will have every modern comfort during your relaxing getaway and may not want to leave. Don't miss out on a true lakefront gem, book today!

Stone Mansion Sleeps 10-20 Free parking & TV

Giant, 4 bedroom, 2,300 square feet apartment on 2nd floor, near Red Line Train, bars, cafe's, shopping, restaurants, Lakefront and everything else Chicago has to offer. Large living room with bar area, TV and fridge for socializing before hitting the town. Dining room has a large table and 8 chairs. 4 bedrooms with 2 private rooms with king beds and one with a double bed. 4 futons for in the living room for extra sleeping space two (2) parking spots in the west facing garage on premises.

Modern MAG Mile 2BD/2BA (+Parking/Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Parking spot on-site in/out access!! - Tranquil rooftop overlooks Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows

Spacious & Elegant N Side Apt Near Beach & Transit

This spacious 1-bedroom apartment, just 1 minute from Marion Majony Griffin Beach, offers comfort and convenience for solo travelers, couples, or small families. Enjoy a fully equipped kitchen, cozy pull-out couch, and a dedicated workspace perfect for remote work or studying. Free street parking is available, or take public transit just a block away to the Red Line for easy access to the city. With its prime location and thoughtful amenities, we warmly welcome all travelers to our listing.

Sheridan Beach Apartment

Keep it central at this place! This basement apartment not only comes fully stocked with an in-unit washing machine, but a full kitchen with all new appliances. The unit is a PRIVATE apartment in a single-family home that is 10 steps away from the nearest CTA Bus stop, 2 blocks away from the redline, and ONLY 100 STEPS AWAY FROM THE BEACH on Lake Michigan 😄 Any and all drug use is a prohibited here. Any and all pets are prohibited here as this is a clean and newer construction.

Spacious & Stylish 2BR-2BA Apt Steps from The Bean

Enjoy this comfy, renovated and super spacious 2BR and 2BA apartment in the heart of Chicago's Loop with views of Lake Michigan. Surrounded by the most popular stores and restaurants, this unbeatable location is less than a one-minute walk to Michigan Ave, Millennium Park, State St. Shopping, The Chicago Theatre and Chicago’s landmark, ‘The Bean'. It is an ideal location to move around in public transportation, as all CTA lines and plenty of bus lines are just within two blocks!

Free Parking| King Bed |Private Balcony |Sleeps 8

Your stylish city escape—unwind, explore, and experience Chicago like never before. Our modern, spacious condo is perfect for families, groups, and business travelers looking for a comfortable, stylish, and well-located stay. Whether you're in town for a concert, conference, sightseeing, or a weekend getaway, you'll find everything you need for a relaxing stay. ONE SECURE INDOOR PARKING SPOT IS INCLUDED❗❗❗ ✨ Book your stay today & experience Chicago in comfort and style! ✨

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This cozy AirBnb is perfectly situated. A beautifully clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation & restaurants, red line "El" trains & bus routes. Apt has private, queen bedroom, en suite full bathroom, living room w/queen sofa bed, TV, dining table, & partial kitchenette. NOTE: No full kitchen.

Fully renovated modern 2 bed apt

Enjoy a stylish experience at this centrally located place! Fully renovated apt, 2 bedrooms with TVs, 1 modern bathroom plus full kitchen and laundry room, beautiful front yard with a Koi fishpond :) 2 miles to downtown, if you are adventurous, you can even walk to the center! Supermarkets and restaurants walking distance! free parking, quiet area to enjoy and relax, public transportation a block away from the property and 10m to downtown. Unbeatable opportunity!