Holiday rentals with a patio in Chicago

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE with garage parking! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

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

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Explore Chicago's charm just moments from downtown! This Airbnb boasts a spa bath with a luxurious rain shower and jetted tub, a fully equipped kitchen for culinary adventures, comfortable reclining sofas for relaxation, and ample space to unwind. Sleep like royalty in the master bedroom's king bed, and a queen murphy bed in the living area ensures a comfortable stay for up to four guests. Step outside to the patio with a fire pit for cozy evenings. Your Windy City getaway begins here!

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

Comfy Studio, NearTrain w/ Parking, Sleeps 4

Escape to an enchanting garden studio nestled in Oak Park's famous historic district. Discover our private urban farm with full gardens and 6 cheerful hens. Stroll to charming stores, cafes, and restaurants, or hop the nearby "L" for effortless Chicago adventures. Free parking, easy airport access. This serene, non-smoking studio with a kitchenette requires no check-out chores. No parties, 4 guests max. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

Large 2BR, 2BA, patio, sunroom, W/D, L-kitchen

Welcome to our charming home in the peaceful yet centrally located Buena Park neighborhood, housed in an updated antique building. This prime location offers easy access to the Red and Purple train lines, as well as multiple bus routes, making it easy to explore Chicago. You’ll be within walking distance of Wrigley Field, Clark St. bars, Montrose Beach, Lakeview, Boystown, and the iconic Green Mill. A perfect blend of quiet comfort and proximity to Chicago’s best attractions.

Old Irving Park- Sweet Garden Suite with Spa

Enjoy our unique, recently renovated, garden suite (basement). Every corner, a pleasant surprise in Old Irving, you will be surrounded by cafes, breweries, and restaurants. You'll have the best of both worlds - the conveniences of the city combined with the charm of a tucked-away garden oasis. Steps away from the train, there is direct train transit to ORD) + downtown. If you do decide to drive, the drive is 15 minutes downtown. Oh did we mention we have a hot tub...

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).