When the summer season begins, even lovers of the Windy City look for romantic getaways near Chicago. Waiting out that winter weather gets couples in the mood for sunshine and fun time. Pick out a rental home in one of these romantic Chicago weekend getaway locations for couples and appreciate the local life.

  1. Lake Geneva, Wisconsin

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    Celebrate the summer months with a weekend getaway to the cool blue waters of Lake Geneva, WI. Located just under two hours from Chicago, this pretty lakeside town invites romance with spectacular sunsets and quaint restaurants. World-class resorts featuring golf courses that bring in the pros and rows of Gilded Age mansions make heading to this lake town a trip worth taking. Lake Geneva offers lovely rental homes and cabins within walking distance of the freshwater beaches.

  2. Galena, Illinois

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    A main street filled with cute antique shops and cozy restaurants makes Galena, IL a favorite for that romantic getaway near Chicago. Located about three hours from the Windy City, Galena is the home of the historic Belvedere Mansion built in 1857. Wander the halls of this pre-Civil War Era Italianate home, and enjoy guided tours during the spring, summer and fall months. Galena’s parks include Thunderbay Falls, a series of waterfalls that makes a lovely backdrop for those romantic photos. Snow skiing at popular resorts in the winter months provides Windy City couples with a little excitement followed by hot cocoa and a crackling fire.

  3. Mackinac Island, Michigan

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    Hop in the car and head just over six hours outside of Chicago to take a huge step back in time. Historic Mackinac Island is one of the few places in the world where horse-drawn carriages are still the primary mode of transportation. Slow down, sit back and enjoy the views of gorgeous mansions and miles of white beaches. Rent your own carriage and horse or choose a bicycle to explore the island. Shops, restaurants and exciting nightlife draw visitors to Mackinac Island throughout the year.

  4. Grand Rapids, Michigan

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    Bright and bustling, Grand Rapids shares an eclectic mix of beer breweries, art galleries, shopping districts and river views. This Michigan city is the home of the Gerald L. Ford Presidential Museum and hosts an annual Festival of the Arts that attracts visitors from all over the world. Romantic couples appreciate the pretty river walks along the Grand River and have the opportunity to explore local theater as well as see a complete opera series. Summertime in Grand Rapids begins with beer festivals featuring Brewers Vivant and Founders. Rental homes and apartments abound in this city, making mingling with the locals a breeze.

  5. Ottawa, Illinios

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    Romance is alive and well with a weekend in exciting Ottawa, IL. This pretty park-filled town is located just 90 minutes from the heart of Chicago but feels like a world away. Wandering the trails at Washington Square Park gives couples a chance to view historic memorials and fountains. Check out the art sculptures at Peck Park, or head inside for a delicious dinner at one of the many fine dining restaurants in the business district. Ottawa offers plenty of outdoor activities and a bustling nightlife that includes craft breweries and wineries.

  6. 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.

  7. 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.

  8. 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.

  9. 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.

  10. 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.