There are tons of great romantic weekend getaways near Chicago, but choosing the right one takes a bit of research. These different road trip-ready weekend vacation spots offer something for every kind of couple, and they all have vacation homes waiting for you to rent.

Cedarburg, Wisconsin

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Though it’s quaint all year round, Cedarburg is a particularly great spot for couples to hit up in fall and winter, when they can pick pumpkins or get a fresh-cut Christmas tree. There are plenty of opportunities for scenic proposals in this part of Wisconsin, and the historic architecture in the downtown area can make you feel like you’re worlds away from the big city.

Carbondale, Illinois

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Carbondale provides easy access to the Shawnee National Forest, which is the perfect place for outdoorsy couples to make some incredible memories against the beautiful backdrop of natural rock formations at the Garden of the Gods or Little Grand Canyon. Though Carbondale itself is more of a quaint college town, that may be just right for the kinds of couples who see the romance in nature.

Saugatuck, Michigan


Known as an LGBT haven in the Midwest, Saugatuck is home to Oval Beach, a sandy shoreline that’ll make you feel like you’re at the ocean rather than on a lake. Gay-friendly hotels provide respite for couples looking to relax and be themselves without worrying about potential disapproval in a small-town atmosphere. Of course, all couples can also find plenty of romantic appeal in this small town. The beach is for everyone, and if you can’t exactly afford a trip to Hawaii, Saugatuck might be the next best thing.

Kalamazoo, Michigan


Want to feel like a king or queen for your weekend away? It doesn’t get more romantic than Kalamazoo’s Henderson Castle, a gorgeous 19th-century estate that really does look like a castle. The castle now operates as an inn and wedding venue, making this a perfect getaway for couples who are auditioning unique places to tie the knot. Beyond the castle, Kalamazoo is an apple-picker’s dream, and there’s a lot of fresh fruit and cider to go around during the harvest season.

Louisville, Kentucky

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Believe it or not, Louisville isn’t that far from Chicago, though its Deep South charm can make you feel like you’re on a different planet. Louisville is a great place to take in two of Kentucky’s great passions: horse racing and whiskey drinking. If watching horses race around a track isn’t your idea of a great date, a distillery tour may be right up your alley, particularly because many of the distilleries in Louisville are still housed in historic buildings on beautiful rolling properties. Couples who like to live on the goth side of life may appreciate Louisville’s massive Cave Hill Cemetery, a historic graveyard with beautiful grounds that are just right for a picnic.