Once the cold weather ends and the summer season begins, local Chicago couples may find themselves looking for a romantic getaway full of sunshine in the neighboring areas. Taking a nice break from the city with your significant other is sometimes essential. 

Whether it’s a long holiday weekend to Lake Geneva or a quick 1 hour 35 min trip to St. Joseph, Michigan, your romantic weekend getaway is well needed and deserved after a long cold winter in Chicago. If you can’t wait till summer and need to take a break from the cold city, we must include, many of these recommendations are also great winter destinations.

Read on for 10 picks on our favorite romantic weekend getaways near the Windy City!

Galena, Illinois

Our first pick is the small town of Galena. With a main street filled with cute antique shops and cozy restaurants makes Galena, IL a favorite for that romantic getaway near Chicago.  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.

Things to do in Galena:

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. 

Get a taste of Galena’s art scene at the Artist’s Annex. Take a pottery class, shop the gallery, and support local arts! 

Driving time from Chicago: 3 hours 

Lake Geneva, Wisconsin

Celebrate the summer months with a weekend getaway to the cool blue waters of Lake Geneva, WILocated 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.

Things to do in Lake Geneva:

The 26 mile shore path is a beautiful trail that displays the rich views of Lake Geneva. Stroll at your own pace and meet friendly locals while taking in gorgeous scenery. 

Located in the heart of Lake Geneva, make sure to check out the Geneva Lake Arts Foundation-Gallery 223. Gain a perspective of the local scene through the unique local artists of this delightful town.

This historic amphitheater is located just 20 minutes away from Lake Geneva. Check the venues calendar and see if your favorite artist is going to be in town during your stay.

Driving time from Chicago:1 hour and 45 minutes

Mackinac Island, Michigan

This destination may require a long weekend due to this distance from Chicago and the fact that it is only accessible by boat!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 sand beaches. Shops, restaurants and exciting nightlife draw visitors to Mackinac Island throughout the year.

Things to do in Mackinac Island:

What is more romantic than riding around in a horse & buggy? 

Take in the vibe of minimal cars and explore this beautiful island with your loved one in this lovely method of transportation. 

  • Rent Bikes

Explore the island at your own pace by renting a couple of bikes! Enjoy the views, and grab a bite to eat at one of the many local restaurants this charming island has to offer.

Driving time from Chicago: 6 hours and 30 minutes + a 20-minute ferry ride.

  1. Grand Rapids, Illinois

Bright and bustling, Grand Rapids shares an eclectic mix of beer breweries, art galleries, shopping districts and river views. 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. 

Rental homes and apartments abound in this city, making mingling with the locals a breeze.

Things to do in Grand Rapids:

This Michigan city is the home of Gerald R. Ford Presidential Museum and hosts an annual Festival of the Arts that attracts visitors from all over the world. 

  • Beer Festivals

Summertime in Grand Rapids begins with beer festivals featuring Brewers Vivant and Founders.

The near 200- acre viewing grounds features an exciting and comprehensive outdoor sculpture collection and the state’s largest tropical garden.

Driving time from Chicago: 3 hours

Ottawa, Illinois

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. 

Things to do in Ottawa:

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. 

  • Enjoy the Nightlife Scene

Ottawa offers plenty of outdoor activities and a bustling nightlife that includes craft breweries and wineries.

Driving time from Chicago: 90 minutes

Cedarburg, Wisconsin

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.

Things to do in Cedarburg:

Check out the awesome history of the bridges in Cedarburg, Wisconsin. Enjoy a nice picnic by the water by visiting this beautiful and historic location.

Enjoy a glass (or a tasting) of delightful fermented grape juice from Cedarburg’s premier winery! This historic establishment opened its doors in 1972. Take a bottle home to remember your trip.

Driving time from Chicago: 2 hours

Carbondale, Illinois

Another recommendation that is probably best for a long weekend trip is Carbondale, Illinois.Lakes, rivers, lush forests, makes for an epic nature setting.

Though Carbondale itself is more of a quaint college town, that may be just right for the kinds of couples who see romance in nature.

Things to do in Carbondale:

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. 

Gain perspective of African American history at this midwest museum. This nonprofit organization is run by volunteers and has been open since 1997.

Driving time from Chicago: 5 hours and 30 minutes

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.

Things to do in Saugatuck:

After climbing just 282 stairs you’ll have an epic view of Oval Beach. Enjoy the world class taste of nature with this one mile hike.

Grab a sip of premium wine and take an in person tour of this exciting facility.

Driving time from Chicago: 2 hours and 30 minutes

  1. 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.

Things to do in Kalamazoo:

Enjoy a fine collection of 20th-century art and check out authentic work by ​Dale Chihuly, Andy Warhol, and Deborah Butterfield among many other prestigious artists.

Check out the thrilling collection of classic automobiles at this top 5 auto museum. Find your favorite out of over 325 unique models.

Driving time from Chicago: 2 hours and 30 minutes

Stay Local!

Who doesn’t love playing tourist and going on vacation in their own city? Get a nice hotel, enjoy a pro sports game, eat awesome food, without having to travel far!

Things to do in Chicago:

Enjoy and savor the culinary experience at this world class, Michelin rated restaurant. 

Experience the thrill of the aesthetic floral gardens that the Windy City has to offer. This establishment features many events year long. 

Find what turns your eyes and head on over.

Let’s get this weekend getaway started! 

Your romantic getaway that you have been looking forward to for a long time starts now! Pack up the car, and start the journey to the destination that you and your loved one will remember forever.