Ferienunterkünfte am Wasser in South Side

Brand New Chicagoland lakefront home

Newly built Chicago lakefront home completed end of 2025. A peaceful lake is pictured in the photos. The space is intentionally styled with a fully furnished primary suite, & additional furnishings are being added to complement the home's modern design. Ideal for guests seeking a calm, elevated stay in a brand-new environment. Only 30 minutes from downtown Chicago in Lynwood, & close to the shops, stores, & restaurants of Schererville, Indiana. Also, 30 minutes from Indiana Dunes National Park.

Cozy Studio Apt near the lake on the Northside

Enjoy a stylish experience at this centrally-located place. 5-7 minute walk to the red & purple lines, & lakefront. Located between Loyola and Northwestern in Rogers Park neighborhood. Newly renovated studio space w/ Murphy bed and attached desk that folds open & close. 1 comfy chair & mini 2 seater bench. Central air, indoor fire place, washer & dryer in unit, dishwasher, TV food trays, & plenty of closet space. Street parking ( usually busier at night) We hope you enjoy your stay with us.

Family Friendly Farmhouse + Arcade + Creek View!

Welcome to your modern farmhouse retreat, freshly renovated with comfort and style in mind. This updated 2 bed, 2 bath unit features a sleek kitchen with quartz countertops, new appliances, and a cozy coffee bar. Relax with a 55 inch TV, electric fireplace, or PAC MAN arcade. A workspace and laundry add convenience. Outside, enjoy a spacious yard with creek views, swing set, patio, and private fishing spot. Perfect for families, couples, or extended stays seeking comfort, fun, and relaxation.

Bike & Kayak: Lakefront Prospect Heights Home

2 Soccer Goals w/ Soccer Balls | BBQ Ready | 2 Mi to Train Station | < 30 Mi to Chicago Explore nature or suburban and city attractions when you stay at this lakefront vacation rental in Prospect Heights. Located 2 miles from the train and less than 30 miles from Chicago, the 4-bedroom, 3.5-bath home makes it easy to access endless activities. Take the kayaks out on the lake across the street, stroll through The Grove, book a tee time at Old Orchard Country Club, or cool down at Lions Pool!

Lakefront View Getaway Home! Hot tub! Kayak!

INCREDIBLE 5,519 sq. LAKEFRONT HOME with GORGEOUS VIEWS. 30 Minutes Away From Downtown Chicago. 7 Bedrooms, 9 Beds, 2 Additional Sofa Beds & 4 Baths. Fits 20 guests by request. PRIVATE DOCK and PATIO/BACKYARD Right on BROOKERIDGE LAKE. UNICORN ISLAND FLOATING RAFT, KAYAK, PADDLE BOAT, FISHING & MORE. BrookeRidge Private Jet Airport in the Same Park. Indoor Entertainment Including POOL TABLE, AIR HOCKEY, PING PONG, DARTS, CARD GAMES, GAMING CONSOLE & KARAOKE 🎤

Westmont 3/2 duplex Fire sunsets, Firepit, lake

Near great shopping and dining. Enjoy wonderful sunsets and quiet lake activity. Fully Stocked 20 acres lake with a neighborhood beach next door. Easy commute to downtown while enjoying the peace and quiet. Feel like you are on vacation every day. Perfect for a staycation. Cleaned to Cdc standards. This duplex is a gem in Western suburbs! Pet friendly (fee). Fire pit (bring Wood), paddleboat, kayaks. Grill and fully stocked kitchen.

Spacious and Newly Renovated 1BR Next to the Beach

1st-floor unit with one flight of stairs. Older building with radiant heat managed by the building. Enjoy our cozy 1BR/1BA apartment near Lake Michigan in Evanston. Features a fully equipped kitchen, a comfortable bedroom with a queen bed, and a clean bathroom. Walk to beaches, the lakefront, and vibrant downtown with shops and restaurants. Easy public transit to downtown Chicago. Book now for a memorable stay!

Tranquil Pondview + New Kitchen + King Bed + WFH

Convenience is at your doorstep as our guest house is centrally located near all major shopping centers, highways, train stations, and restaurants. Retail therapy awaits at the nearby Oakbrook Center, where you can indulge in a gratifying shopping spree. If you're planning to explore the city or neighboring attractions, easy access to highways and train stations means you're never far from your next adventure.

Bronzeville Tribe Palace Loft

- Centrally located: downtown - 10mins, McCormick Place - 5mins, Solider Field - 7mins, US Cellular Field & Lakefront - 5 mins -Security cameras outside and in common areas - (2) queen-size beds, (2) twins & couch converts to a sleeper - (2) desk - (4) 4K smart TVs in each room - Fully equipped kitchen w/ Oat meal, fruit, coffee & teas provided - Spa quality soaps & towels provided - street parking

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

Relax with the whole family or explore the city with friends at this peaceful and spacious 3-bd/1.5 ba condo tucked on a quiet, tree-lined street. Includes one (1) free parking space, plus plenty of unmetered parking on st. Minutes away notable hospitals, both Northwestern, and Loyola Universities. Travel via CTA bus stop at the corner. Only 30min drive from downtown Chicago. PET & 420 FRIENDLY!

Lake Home-3 blocks to beach/harbor10 min 2 Loop!

Spacious 5BR, 3.5BA home in historic Bronzeville, just 3 blocks from the lakefront and under 10 minutes to Downtown Chicago. Features a large living room, dining space for 12, entertainment room, butler’s pantry, backyard, and 2-car garage. Keyless entry, refreshed furnishings, and professional cleaning before every stay. Close to beaches, parks, transit, and major Chicago attractions.

Cozy 5-bedroom with lake views and spacious deck

Enjoy vacation views in the western suburbs, when you book this spacious 5 bedroom 2.5 baths. Conveniently located between Oak Brook, Hinsdale and Clarendon Hills, you'll find no shortage of parks, restaurants and entertainment nearby. With a fully stocked kitchen, office space, a 2-car garage and child-friendly rooms, this property is a fantastic fit for your family!