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.

NEW! 3BR/2.5B Duplex in Noble Sq

Welcome to our stunning 3 bedroom, 2.5 bath duplexed condo with free parking and ample outdoor space in the heart of the vibrant Noble Square neighborhood. This open, bright and spacious unit is a true urban oasis that will make you feel right at home in the epicenter of Chicago. Our condo is close to some of the city's best restaurants, cafes, and bars, as well as several beautiful parks. With its unbeatable location, modern design, luxurious amenities, and SuperHost service - look no further!

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

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.

BoHo House | Chic, 1903 Chicago Workers Cottage

Welcome to BoHo House – a charming, airy bohemian gem built in 1903. This beautifully designed 3BR home is just a short walk from Chicago's popular bars, restaurants, and coffee shops. Enjoy the peaceful private fenced backyard, perfect for your pup to roam, complete with an adorable outdoor space. Host a cozy patio dinner by the fire or unwind indoors with a movie. Just 20 minutes from ORD, 10 minutes to downtown, with 800+ Mbps WiFi, free coffee, and secure 2-car garage parking!

Sophisticated Twnhm in Prestigious Lincoln Park

Welcome to our awesome townhome, nestled in a peaceful residential neighborhood, offering both convenience and serenity. Located with easy access to public transportation, you can explore all that Chicago has to offer. There are multiple levels to this townhome with stairs. A bedroom and bathroom on the ground floor, kitchen and living/dinning room on the middle floor, and the master bedroom with master bathroom on the top floor. A mini roof top to enjoy Chicago nights as well.

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).

Kid friendly 2 bedroom w/ private office

Private first-floor 2-bed apartment in hip Logan Square. Full bath, kitchen, WFH space and separate entrance. Walk to restaurants, cafes, parks, Blue Line/bus, 5 mins from bike rental/606 trail. We are kid/family friendly! We live upstairs with two young kids. Our ideal guest is comfortable with some family noise and apartment living. Cozy, convenient, and perfect for travelers seeking an authentic neighborhood stay! Please read other notes for more info!

3 bed/2 bath by United Center w/ private parking

Welcome to the Windy City White House – a spacious, historic 150-year old home 3 blocks from the United Center & mins from downtown. 3 bedrooms feature luxury bedding. 2 bathrooms – 1 newly redone w/ a large rainfall shower head. Private deck w/ seating. Spacious living room w/ work space. Fully equipped kitchen. Private parking. It's the perfect place for friends, families, & business travelers to relax in ultimate comfort after a day exploring the city.

Whole apartment! 2 Bed/2 bath steps from Wrigley!!

Newly rehabbed urban nest among the tree-lined streets of beautiful East Lakeview. Literally 60 seconds to Wrigley Field, close to bars, restaurants, El train/busses, and lakefront. You’ll have loads of space in this 2 bed, 2 bath, plus office and large laundry room with FREE full size W/D. Free parking passes! Owner lives near by and is happy to help with anything you need to make your trip the best it can be. Flexible check in/out times upon request.

Victorian House in Heart of Rogers Park

Newly restored Victorian house giving you a touch of Chicago's history with modern comfort. Feel at home away from home with fully equipped kitchen, entire house, and outdoor spaces with beautifully landscaped garden for lounging, grilling, and chilling. Large screen TV in living room and TVs in each bedroom. Fast Wi-Fi throughout the house. Walking distance to public transit, restaurants, bars, beach and shopping. Designated parking. #TheCatalpa

Cozy Home in Brookfield

Discover tranquility just minutes from the busy city life! Nestled in the heart of Brookfield, IL, our charming home offers the perfect blend of suburban serenity and urban convenience. Just an 8-minute walk from the train station, you'll find easy access to downtown Chicago while enjoying the peaceful atmosphere of our neighborhood. Max 4 overnight guests. No parties or events. Pets allowed (no exotic pets or animals with a bite history).