Holiday rentals with a patio in South Side

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Pet Fndly

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 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 with exceptional landscaping. The property has a car port in back which 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! NO CHORES! Please reach out with any questions you may have before booking Hot tub 5-6 Person Spa

Blue Brick Apartment in Bridgeport - Park for Free

-600 sq.ft apartment / 2nd floor / Patio Deck -Free parking pad in rear / free street parking -Commute to Downtown: 15min (drive) / 28min (transit/train) / 22min(bike) -Walk score 93! Bike Score 92! Near Trains to Downtown!! -Gated access w/ Building video and security alarm system and noise monitoring equipment. -Kitchen is stocked w/ cookware, utensils, etc. -Washer and Dryer and Dishwasher in unit (free) -Rideshare(Uber/Lyft) / Bikeshares(Divvy) are bountiful -Safe, working class neighborhood

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.

Fun & cozy getaway w/POOL/game room/FREE parking

Enjoy our Pool & Play Getaway in hot Logan Square! Thoughtful upscale touches throughout. Conveniently located on a tree-lined Chicago Cul-de-Sac, just a 5 min walk to the L Blue Line. Relax in our extended outdoor living space, spend an afternoon lounging in the pool, al fresco grilling & dining on the deck or toast smores over the firepit in the yard. We're steps from all the hot restaurants and nightlife, including Chicago's #1 farmer's market. Free permit street parking for our guests.

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Millennium park 10 min Free P-Spot&Balcony Sleep 8

FREE & SECURE ONE IN-DOOR PARKING SPOT!!! You would enjoy staying in the spacious 1800 sq ft with 10 ft high ceilings. 2 bedroom/2 bathroom apartment with ZERO STAIRS to get inside! It is an excellent solution for elder people and families with kids or maybe just a group of friends coming to have fun at the UNITED CENTER sports event or tourists as well as business folks or doctors to attend McCormick Place conferences. Bring the whole family to this great place with lots of room for fun.

Spacious 1BR Garden Apt & Parking

Welcome to our tranquil garden apartment on a quiet residential street near the university and all Hyde Park attractions. Enjoy morning light through picture windows in the spacious living room and adjacent kitchenette. Breakfast on the patio or garden bench on a sunny morning. Stroll to one of 20+ eateries within four blocks. We are on-premises hosts and owners, available for whatever may arise. Access is private via back gate just off the parking lot with reserved parking space.

South Loop 2BR Near McCormick & Lakefront w/ Patio

Welcome to your modern escape in Chicago’s vibrant South Loop, just steps from the iconic McCormick Place! This luxurious 2-bedroom, 2-bathroom suite is thoughtfully designed to provide comfort, functionality, and style—perfect for families, business travelers, event-goers, and leisure seekers alike. 🌆 📩 Message us for SPECIAL RATES & long-term discounts! Whether you’re attending a conference, visiting a museum, or exploring the lakefront, you’re just minutes from it all.

1 bed apartment + futon room bridgeport

Located at the geographic center of Chicago! Plenty of free street parking. Very safe and ~10 min walk to the 35th Orange line and 3 blocks from the Archer bus, both go directly downtown within minutes. Brand new lower level construction unit. Comfortable spacious rooms to relax in. Closet in both rooms for your use while here. The apartment has a separate entrance, bathroom, kitchen, dining space. Enjoy your own private space in Chicago with a back patio, grill, and laundry.