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Skyscrapers dot the shore of Lake Michigan in the famous Windy City. Stroll through the Millenium Park, browse multi-million dollar artwork at the Art Institute of Chicago, or admire the view from the top of the 360 Chicago Tower. Chicago is pedestrian and cyclist friendly, and with a fantastic subway system, you can effortlessly venture into every corner of the city. Staying at a vacation rental is the next best thing to living in the Windy City, and these self-catering stays will make you feel right at home.
A hugely sought-after spot in bustling Wrigleyville, this 1894 red-brick coach house is full of surprises. Set back from the street, it’s a little rustic oasis, and has recently been renovated with plenty of contemporary features. This place is ideal for families, with four bedrooms and room for eight, there are plenty of neat details the kids will love, including a secret play space and a walk-in toy closet. With its prime location near Wrigley Field, the park, zoo and beaches, this Airbnb is a solid family vacation option.
This River West spot is more than just a loft space. It’s the pad for you if you’re looking for a place to unwind, hang out and enjoy some quality time with friends or family. A surround-sound cinema room, jacuzzi and pool table add to its appeal, along with cool hanging chairs and an inviting industrial-retro aesthetic. Sleeping up to eight guests split across four bedrooms, and with three bathrooms, this is luxury lofting at its finest. And while it is tempting to just stay in the space and chill, there are plenty of attractions within walking distance in the nearby Wicker Park and Bucktown neighborhoods.