House holiday rentals in Chicago

Cool Quiet Coach House, Private Access + Patio

Retreat to the brick patio of this lovingly renovated home after a long day traversing the neighborhood. The interior is an expression of creativity, greyscale walls, rustic accents, and a varied selection of art and wall hangings tie in the decor. Split Level Floor plan. 1st floor = Living, Eat in Kitchen, bedroom 1 and bathroom. 2nd Floor = 2nd bedroom , bath and an additional sleeping area and desk area. Also features a gorgeous shared yard. The entire coach house is yours!! The coach house is set back behind a 2 unit building and the yard is shared between both. We are available via text or airbnb messaging and try to respond quickly. Please reach out anytime if you need anything at all. Extra supplies, neighborhood recommendations or tips in the neighborhood. The home is located on the border of Wicker Park and Bucktown which is Chicago's original hub of cool. It is a vibrant enclave of culture and commerce, explore vintage finds, record stores, and plenty of indie shopping in this trendy part of town The 24 hour Blue Line EL train is just a 5 minute walk. Door to Door it's only 25 minutes to Millennium park. (5 min walk to the blue line, 10 min ride on the train, 10 minute walk to the Park). The neighborhood is pedestrian and bike friendly , the 606 trail is just a few blocks away also.

Large Home | Free Parking | Near Downtown

• HUGE Single Family Home | 3 Floors • Parking Garage | 2 Cars! • Chef's Kitchen | Cookware | Utensils • Basement | Two Living Rooms • 4 Bedrooms | 5 Beds | Sleeps 10 • Downtown | McCormick Place: 10min(drive) • Soldier Field | Sox Stadium: 10min(drive) • Chinatown | Pilsen Nightlife: 5min(drive) • Lakefront | Beach | Museums: 10min(drive) • Outdoor Surveillance | Noise Monitoring • Washer | Dryer | Dishwasher in unit (free) • Rideshare(Uber/Lyft) | Bikeshares(Divvy) • Working Class Neighborhood

Private Downtown Retreat with Rooftop Oasis

Welcome to your exclusive retreat in the heart of the city, where urban sophistication meets unparalleled comfort. Nestled in between Magnificent Mile and Gold Coast, this luxurious Airbnb offers a haven of style and tranquility amidst the hustle and bustle. The rooftop patio offers incredible views of the city skyline, with touches of lush greenery. The spacious living areas boast oversized windows that flood the space with natural light. Each bedroom is a sanctuary where luxury meets comfort.

Luxury SOHO Styled Two-Level Townhouse - Old Town

NEWLY CONSTRUCTED TOWNHOUSE IN THE HEART OF OLD TOWN! This private luxury townhouse (duplex) is perfectly located in vibrant Old Town-surrounded by nightlife, restaurants, cultural attractions, and is only a 5 min walk to the beach, steps from Lincoln Park, and next to Second City. This 2,800 square foot townhouse features 13 foot ceilings, open floorplan, private patio, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between.

Charming 3-BED in Lincoln Park/ Old Town & Parking

Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.

The Chicago River House – GIANT wall projector!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

The Full House

A tranquil space surrounded by natural light and embraced by lush greenery. This entire house, with a backyard and parking garage, is in a peaceful neighborhood with tree-lined streets. Just 3 miles from downtown Chicago. A 2-minute walk from public transportation. For local delights, Wicker Park/Humboldt Park beckon with excellent dining/cultural experiences at your doorstep. "When you're lost out there and you're all alone, a light is waiting to carry you home..." Welcome to the Full House!

UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)

Escape into this Wicker Park Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Division St. - Close to every popular attraction that makes Chicago so great - Luxurious interior filled with natural light - Open-floor plan for entertaining! - City skyline views from top floor! - Fast WiFi (1,000 mbps) - Large attached garage! - Beautiful custom built-ins - Next to modern park and playground! - 10 minute walk from blue line (CTA L)

The Ashlin House.

Stay at our family-friendly home on a quiet, cobblestone street on vacation or business. We've recently repainted the exterior and painted the master BR. Walking distance to quaint Downtown Whiting , Lake Michigan, Whihala Beach & Lakefront trails. The Horseshoe Casino, Wolf Lake & Pavilion, Hammond Sportsplex, Calumet College, PNW, IUN, U of Chicago, BP, & golf courses are a short drive. See Chicago's Skyline at Lakefront Park. Chicago's attractions & Hard Rock Casino are < 30 mins away.

Modern Gazebo Sleeps 17 Birthday Anniversary

Treat yourself to this Chicago getaway with 16 of your friends & family. Be inspired to create culinary delights in our celebrated 5 stars outdoor kitchen. Reboot & relax in each of our thoughtfully designed powered by SOLAR ENERGY throughout. After a memorable night in OR an adventurous night out you will ask yourselves, 'Why don't we do this more often?' 15 mins to Downtown, O’Hare airport, West Loop. 20 mins to Lakeview, Wrigleyville, Boystown, Logan Square, Bucktown & Wicker Park.

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

*Due to AirBnB new changes in fee disclosure, 18% of the daily rate you see goes to Airbnb* 1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (2 Queens) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard. A parking space in the rear allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! Please reach out with any questions. NO CHORES!

Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!

No cleaning fees! Gorgeous gem 10 miles from Downtown, Airport, Lake Michigan, and United Center! 15 miles from Wrigley Field and the Zoo. Next to CTA! 6 bedrooms 2 bathrooms, 10 beds. Sleeps 18 comfortably. Perfect for large groups! Modern smart home with air hockey, pool table, video games, 2 ping pong tables, foosball, 9 big screen TVs including 85" Samsung QLED with surround sound, outdoor dining, charcoal grill, cornhole, dining room, game room, 2 living rooms, and full kitchen.