Condo vacation rentals in Woodlawn, Chicago

Convenient & Spacious 3BR Condo w/Free Parking

Get cozy in this spacious 3-bedroom condo, conveniently located 3 blocks from the Halsted Orange Line overlooking Palmisano Park and only 5 minutes' drive to McCormick Place. Clean, neat, modern and comfortable, the condo offers spacious living space with an open kitchen, washer/dryer, and an outdoor balcony perfect for families and groups. Hungry? Our complex offers a few delicious high rated yelp restaurant options to fulfill your appetite. We look forward to hosting you and your guests!

Stunning, Spacious, & Sunny 2bed Uptown Condo

Welcome to your home away from home in Uptown! My bright and inviting condo offers a perfect blend of comfort and convenience, with your own sunny living room to relax, fully-equipped kitchen and separate dining room, spacious private bedroom, serene sunroom with full bed for extra guests, and a workspace for business travelers. Just steps from the lakefront and Montrose Beach, and a 6-minute walk to the Wilson Red Line, this location is excellent for exploring all that Chicago has to offer.

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

This bright and airy 2 bedroom/2 bath condo has been completely renovated with a designer’s eye and creative touch. The condo comes with 2 parking spaces in the adjacent private gated parking lot. The covered patio space on the back deck offers spectacular views of the Chicago skyline – enjoy your morning coffee or evening cocktail overlooking the city. L Train Stops & tons of restaurants, bars and entertainment within walking distance. Please contact me for discounts on monthly stays!

Luxurious River North 3BR/2BA- Free Onsite Parking

Experience an urban oasis unlike any other: - Complimentary parking for one vehicle in our attached lot - Spacious, recently renovated kitchen - Immersive entertainment with large-screen TVs - Unwind with a game of poker or foosball at our dedicated tables - Conveniently located within walking distance of the Magnificent Mile - Surrounded by an array of vibrant bars, restaurants, and nightlife - Embrace our inviting patio Indulge in a memorable stay at our 3rd-floor condo!

Brilliant Downtown Chicago 3-Bedroom Condominium

Situated in downtown Chicago, right next to the Godfrey Hotel, this spacious and bright 3-bedroom, 2-bathroom condominium is perfectly suited to deliver the best adventures the Windy City has to offer. Our vacation home includes four sleeping areas with 1 King & 3 Queen sized memory foam mattresses and features everything from a fully-stocked kitchen to smart gadgets like Alexa. PARKING: We offer a $30 per day parking credit. This credit pays for most or all parking costs.

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Lively Wicker Park 2br, Steps to Damen Blue Line

Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of amenities. Just a block from everything this neighborhood has to offer and 2 blocks from the 'L' to take you downtown or to O'hare Airport. Premium location to effortlessly walk from our quiet side street and be in the heart of all the entertainment! I provide all the essentials to make your stay easy and comfortable!

Steps from the Lake, Lovely 3-Bedroom Condo

Enjoy all that Chicago has to offer in this beautiful Edgewater home. Lakefront beaches are steps away, as is the red-line Granville stop. This condo is walking distance to the Loyola campus, many restaurants, grocery stores, gyms, antique stores, and more! There is ample street parking on Lakewood, often there is a space right outside the house. We provide daily parking passes for you to use during your stay.

City Center Oasis: 3BR/2BA✔︎ Patio✔︎ Parking(2x) ✔︎

Perfectly in the heart of Chicago in the River North neighborhood. You will experience Chicago easily from here! • Free parking (2) in our attached lot! • Surrounded by world class shopping on the Magnificent Mile • In the heart of the city's best dining and walking to big-city nightlife • Walk to Lake Michigan and Navy Pier • Steps from the local trains and buses to reach the outer parts of the city