Family-friendly rentals near Chicago River Walk

Stunning 3BR Penthouse in the Loop | Roof Deck

[NOTE: The main rooftop is currently closed for renovations and is slated to reopen in Summer/Fall 2026. The 2nd rooftop remains open and available to use, including the pool which typically opens around Memorial Day]. Beautiful 1,400+ square foot penthouse apartment on the top floor with 13 foot tall ceilings, oversize windows, and panoramic city views. This bright and airy three bedroom, two bathroom space is perfect for travelers looking for a luxurious escape in the sky in the heart of down

Fulton House #1 (2bd/ 1ba)

Unique & stylishly designed by Chicago's own Outline Interiors, this highly sought after location is for those that want to stay on a calm side street around the corner from city's best, award-winning restaurants and trendiest shopping. The fully-serviced apartment has the business-travel amenities you want: ultra speed wifi, work stations, top tier dining options within steps of the front door, Nespresso coffee, bottled water, washer/dryer. First-come parking next door: $20/nt or $200/mo.

River North | Private Balcony With In&Out Parking

Enjoy a stylish experience at this centrally-located place ✨. Stunning 1,000 square foot modern two-bedroom, one-bathroom unit is perfect for corporate travelers and/or families looking for a stylish escape in downtown Chicago 🌆. 🌇 Rooftop Patio W/ BBQ 🍖 🚗 Free In/Out Parking - 5 Mins Walk To Garage 🌅 Private Balcony W/ Breathtaking Views 🛏️ 2 Bedroom | 1 Bathroom 👑 2 Queen Beds 🛏️ 1 Inflatable Airbed 👶 Portable Crib 📺 Netflix, Hulu, Disney Plus, and Prime subscription Included

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.

Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D

Private 2BR apt. in vintage 3-flat in the heart of Chicago's Michigan Ave/Gold Coast neighborhood. Fantastic locations steps from world-class shopping and restaurants, Oak St. beach, and public transportation (L trains, express bus). Includes A/C, washer-dryer, super-fast wi-fi, smart TV, and workspace. Hourly rate garage parking next door. Note: Guests must walk up one flight of stairs. Light sleepers should bring earplugs as there are noises typical of a big city.

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).

Urban Chic Apartment by the Magnificent Mile

Ideally located just half a block from Michigan Avenue, this bright and open 3rd floor apartment boasts thoughtfully appointed rooms for your comfort so will have everything you need to enjoy your stay in style! PLEASE NOTE: 3rd floor walk up (NO ELEVATOR) There is a small neighborhood bar on the second floor of the building. They are respectful of our neighbors, however they do play music which can be heard in the living room but rarely in the bedrooms.

Bright 2BR-2BA steps from The Bean & Michigan Ave

Come enjoy this comfy and spacious 2BR-2BA apartment just steps away from Michigan Ave and ‘The Bean’, and within a short walking distance to most of Chicago’s most popular landmarks. Within just two blocks, you will find access to all CTA train lines. With a fully stocked kitchen, smart TVs in all rooms and views to the lake, this is the perfect Airbnb for couples, families and business travelers during their time in the city of Chicago.

Loop Loft-Subway & Art Institute

Urban Elegance Meets Prime Location! Welcome to our chic hard loft in the heart of the Chicago Loop. Experience city living at its finest, where industrial charm marries modern luxury. Features: - Authentic loft with polished concrete floors - Soaring high ceilings - Elegantly furnished Location: - Right in Chicago's vibrant Loop district - Walk to Millennium Park, Art Institute of Chicago, Mag Mile, Riverwalk, and more

Chic 2BR Gem with Fireplace

Discover urban luxury in our 2BR, 2BA Gold Coast haven. This stylish apartment boasts a warm fireplace, sleek granite countertops, and a cozy layout. Immerse yourself in city living at its finest, right in the heart of Chicago's prestigious Gold Coast neighborhood. Perfect for both business and leisure travelers, our space combines modern comfort with the vibrant energy of one of the city's most coveted neighborhoods.

50th Floor Mag Mile Views, Balcony, Pool, Gym

The Penthouses at Grand Plaza PH#12: Towering 50 stories above Downtown Chicago, this luxury unit features floor-to-ceiling windows and breathtaking skyline views. Enjoy sunsets, unmatched location, and true urban living. Walk Score of 100 with a grocery store in the building. Amenities include a fitness center, outdoor pool, kitchens, and business center. The city is at your feet—experience Chicago in style.

Coach House in Historic Old Town Chicago

Our coach house is the perfect place for your stay in Chicago. Located walking distance from restaurants, Lake Michigan, the beach and public transportation, it will make your stay in Chicago easy and eventful. We can tell you everything you need to know about the best places in the city. You'll feel right at home here on your Chicago adventure.