Pet-friendly holiday rentals in Bridgeport

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

Ukrainian Village Garden Retreat

A newly updated 1 bedroom, 1 bathroom apartment in Chicago's historic Ukrainian Village. Located a few blocks from Wicker Park, Ukrainian Village is a small historic district of Chicago filled with historic architecture. Access the apartment via a smart lock, the apartment includes everything you need for a comfortable stay, including a queen-sized bed, full kitchen, fiber high-speed internet (100+ Gbps up and down), smart TV, modern bathroom, in-unit washer & dryer, and free garage parking.

Retro Modern Bungalow | free parking | fire pit

Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Vintage Suite Home Chicago by Sox/Park/Transit

Walkout basement studio in a ca.1890 home built for laborers in the Chicago Stockyards - Please read entire listing before booking. This quiet, tree-lined neighborhood is a respite from city buzz. Get downtown in 4 stops by train or any of 5 nearby buses. Your space has great natural light, 2 comfy beds (1 folds to couch), private bath, flexible work/dining area, super-fast WiFi, and kitchen with all the essentials. Private entry via back door Free street parking Se habla español

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.

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...

Eddy Street Upstairs Apartment

Make yourself at home in our comfy, cozy upstairs apartment! Located in the Portage Park neighborhood of Chicago, we are close to great food, parks, and fun outings! You can get to O'Hare Airport in less than 20 minutes, depending on traffic. And we're about a 25 minute drive to downtown, or about 45 minutes via public transit. We have free street parking on our block!

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Garden on Warren

Near West Side / West Loop location, less than 10 minute walk to United Center for Chicago Blackhawks, Chicago Bulls, music, concerts, shows, and events. Close proximity to CTA Pink & Green lines, Union Park, Randolph & Fulton Street dining districts, University of Illinois at Chicago and Rush Medical District. Private entry, very secure and quiet apartment.