13 Charmingly Romantic Getaways in the Midwest

Are you planning a Valentine’s Day surprise, anniversary trip, honeymoon, or romantic weekend in the Midwest with your significant other?

Offering both small-town charm and big-city glamour, the American Midwest shouldn’t be overlooked when planning your next romantic weekend getaway.

Hilltop wineries with panoramic vineyard views, idyllic lakeside towns, and lively cities set the mood for romance at the following destinations for romantic getaways in the Midwest.

Disclosure: This guide to romantic getaways in the Midwest contains affiliate links. I may earn a commission when you click on one of these partner links and book your hotel or activities.

Ann Arbor, Michigan

On a romantic weekend getaway in Ann Arbor, Michigan, twosomes in love can stroll hand-in-hand through beautiful parks and gardens, the sprawling University of Michigan campus, and a downtown full of date-night restaurants, cocktail bars, and live music and performance venues.

Begin your romantic walk through this Southeast Michigan college town at Nichols Arboretum, meandering through over 100 blooming peonies in late spring or under a canopy of colorful leaves in fall.

Then, stroll to the University of Michigan Law Quad, where the grand neo-Gothic architecture is a popular backdrop for couples’ engagement and wedding photos.

As you walk through the charming downtown, browse independent bookstores for literature’s epic love stories, and then settle into a cozy nook at one of the unique coffee shops in Ann Arbor.

Once daytime turns into date night, tantalize your taste buds with Spanish tapas at Aventura, or see if oysters are an aphrodisiac at Black Pearl. Alternatively,  reserve a table for two at the Blue Llama Jazz Club for dinner and live jazz music.

Then, end your evening sipping Thai basil daiquiris and chocolate espresso martinis at Nightcap or tasting whiskeys at the Ravens Club.

By staying at Graduate Ann Arbor, you can peddle through campus on maize-and-blue bicycles or start your downtown Ann Arbor date night with a pre-dinner drink in the hotel’s old-school cocktail lounge.

Weber’s Boutique Hotel & Restaurant offers couples an all-in-one romantic getaway. Without setting foot outside the hotel, you and your sweetheart can relax in an indoor saltwater pool, share a romantic dinner of “famous” prime rib, and dance to live jazz music at the Habitat Bar.

RELATED: Romantic Ann Arbor Date Ideas for Foodie Couples

Chicago

When you’re ready for romance, the Windy City is the place to be.

There are so many romantic things to do in Chicago, it’s the perfect place to celebrate your love, no matter what your interests are.

In the winter, ice skating in Millennium Park is Hallmark movie-worthy. In the summer, the same park not only offers free concerts under the stars, but it is also lovely for a garden stroll.

You can’t help but fall in love, both with each other and with the city, when you take one of the many dining cruises available. There is no better view of Chicago than from a boat on Lake Michigan.

Unless, of course, you’re in one of the city’s sky-high observatories. In the Willis Tower, your love is sky-high at the tallest observation deck in the US, and at The Signature Lounge, located two floors above 360 Chicago, share a toast to your love with a breathtaking sunset view.

The Palmer House Hilton is the perfect place to stay during your romantic getaway. Not only is the lobby one of the most beautiful you’ll ever see, but Potter Palmer also built the hotel as a gift for his wife. Open continuously since 1873, it’s also the oldest hotel in Chicago.

Recommended by Theresa Goodrich, The Local Tourist

RELATED: Where to Eat in Chicago

French Lick Resort, Indiana

If you are looking for luxury and old-world romance, French Lick is the place to find it in Indiana. 

The historic French Lick Resort is as “all-inclusive” as you’ll find in the Midwest. Away from the big cities and the stress of life, the resort offers gorgeous views, quality dining experiences, and extremely comfortable beds.

Tucked away in the rolling hills of southern Indiana, it is one of the state’s most magical places. The resort is also a historic Indiana landmark and is famous for its mineral springs.

When I read about the resort’s history and saw it in person, I was in awe. The French Lick Resort consists of three hotels (the West Baden Springs, French Lick Springs, and Valley Tower), a casino, and golf courses. 

Resort activities include horse-drawn carriage rides, spa services, nightly live music, walking trails, horseback riding, history tours, afternoon tea, biking, and more. 

My husband and I had a romantic getaway at the French Lick Resort, and it’s truly an experience I’ll never forget!

Recommended by Jamie Ward, Cornfields & High Heels 

Kansas City, Missouri

Every list of romantic getaways in the Midwest should include Kansas City, Missouri. Known for its barbeque and jazz heritage, Kansas City is a big city with a charming small-town feel.

Perfect for couples wanting to spend time together, Kansas City offers a variety of attractions. Pairs in love can explore the American Jazz Museum and browse the Nelson-Atkins Museum of Art together by day.

Couples on a budget may also appreciate that many Kansas City attractions are free. Together, couples can see interactive exhibits highlighting the history of greeting card company Hallmark at its visitor center and admire Union Station’s beautiful beaux-arts architecture.

Another romantic thing to do in Kansas City is to walk along the river at Country Club Plaza. In addition to the riverfront walking paths and bridges for your romantic stroll, there are gondola rides on the river from April through October.

From breakfast through dessert, there are plenty of unique places to eat in Kansas City.

Couples should start their mornings at Messenger Coffee Company. This multi-floor space serves quality coffee and pastries made in front of the customers!

Of course, you have to eat traditional Kansas City barbecue while in town. One of the most popular barbecue restaurants is Q39, known for its brisket and burnt ends.

The Ambassador Hotel Kansas City, Autograph Collection is among the most romantic hotels in Kansas City. Its 113 romantic deep-purple-and-gray rooms feature cozy beds with pillowtop mattresses and premium bedding.

Recommended by Vicky, Buddy the Traveling Monkey

Mackinac Island, Michigan

There is something completely enchanting about being picked up by a horse-drawn carriage and whisked away into the woods. A 20-minute, fairytale ride with your love is sure to set a romantic mood on Mackinac Island in Northern Michigan.

Along Cudahy Circle, high atop the island’s West Bluff, you will find two classic Tudor mansions. The largest is The Inn at Stonecliffe, a summer staple for weddings and sweet romantic getaways. Next door, you will find Woods Restaurant with its opulent exterior and colorful Bavarian charm. 

With its unbeatable character and ambiance, Woods Restaurant offers the perfect recipe for a romantic dining experience. Serving fine German cuisine with service that is second to none, each beautiful dish is seamlessly presented and sure to satisfy any palate.

But dinner at Woods Restaurant is more than just a meal; it allows you to experience all five senses.

Arrive a little earlier than your reservation time to enjoy a drink and fresh popcorn at Bobby’s Bar and try your luck at America’s oldest operational DuckPin Bowling Alley.

Then, sit in the Gingham-adorned main dining room, which features a cozy fireplace and nightly piano performances. For an all-natural setting, choose the outdoor patio to enjoy the island breeze among the flower blossoms.

Recommended by Cassondra Scott, Cassondra Wanders The World 

New Ulm, Minnesota

If you have dreamed of taking a couple’s trip in Germany’s scenic Rhine Valley but are looking for a romantic destination closer to home, consider New Ulm, Minnesota.

This small Midwest city with German roots is a lovely place to celebrate your Liebe, and long-haul flights are unnecessary for couples visiting from the continental US and Canada. 

First, check into Bingham Hall Bed & Breakfast, where the Elijah Room’s gas fireplace and two-person Jacuzzi tub set the mood for romance.

Then, you and your Schatz will find romantic things to do throughout your weekend getaway in New Ulm.

On Friday night, go dancing and listen to live music at The Grand Kabaret. 

The following morning, split a strudel at the Backerei & Coffee Shop before wandering over to Bookshelves & Coffeecups, where you can sip gourmet coffee while browsing the eclectic collection of used books. 

Then, continue your exploration of New Ulm’s boutique shops, where you’ll find unique souvenirs to fondly remember your trip. Perhaps you’ll return home with handcrafted furnishings, antique wares, cuckoo clocks, or Christmas decorations. 

In the afternoon, head to Lola – An American Bistro for a charming lunch date. On a warm fall day, order to-go sandwiches and picnic near the Hermann Monument, which offers sweeping panoramic views of the river valley’s colorful fall foliage. 

Beer-drinking couples will love touring Schell’s Brewery, the second-oldest family-owned brewery in the United States.

Afterward, head outside to the Biergarten, dotted with picnic tables under blue umbrellas. On a sunny Saturday afternoon, it’s the perfect place to relax with a German-style pilsner or citrusy Sangria-inspired lager as you listen to live music and share a snack from a local food truck. 

For Saturday evening, plan a wine-tasting date at Morgan Creek Vineyards, where you can listen to live jazz music or share a delicious dinner of European-inspired cuisine.

Finally, end your romantic weekend in New Ulm with a delicious, home-cooked breakfast at your cozy B&B.

Put-in-Bay, Ohio

Island life comes to mind when you’re searching for a romantic getaway. But you don’t need to escape to the Caribbean to find that island vibe with a touch of romance. Instead, the Midwest offers everything you’ll need in Put-in-Bay, Ohio, on South Bass Island in Lake Erie. 

The romance starts with watching the sunset on your way over from the upper deck on Miller Boat Line. Another option is to view the sunset over a seafood dinner at The Boardwalk, starting with an oyster shooter. The deck features stunning views of Put-in-Bay Harbor.

Ashley’s Island House, located just one block from downtown, is an 1860s Victorian Bed and Breakfast. The largest and oldest B&B on the island offers a deluxe continental breakfast. The front porch with white wicker furniture is the perfect place for you and your sweetie to have your morning coffee.

You’ll find luxury in the romantic, calm respite at The Butterfly House, viewing over 50 species of butterflies. Wine tastings are another just-the-two-of-you activity. Put-in-Bay Winery offers the harbor’s panoramic view from the front lawn making it the perfect place to watch boats and relax with a glass of wine. 

Recommended by Amy Piper, Follow the Piper

Saugatuck, Michigan

As a coastal destination along the shores of Lake Michigan, Saugatuck oozes small-town charm with an idyllic waterfront setting, cozy bed & breakfast lodging, and an artsy downtown for your next romantic getaway.

With more than 100 LGBTQ-friendly businesses, Saugatuck is also a welcoming destination for queer couples seeking a romantic escape.

It doesn’t get more romantic than sharing a gourmet picnic lunch from Farmhouse Deli & Pantry aboard a sailboat on a private sail for two.

Back on land, stroll hand-in-hand through a Saugatuck Center for the Arts or Ox-Bow exhibit or while browsing the boutique shops and galleries downtown.

Adventurous couples can climb the 300+ steps to a scenic overlook at Mt. Baldhead Park, hike to the lakeside dunes at Saugatuck Dunes State Park, or go on a thrilling dune ride.

In the evening, dine al fresco at Bowdie’s Chophouse or Coast 236 Restaurant & Bar before watching the sunset over Lake Michigan at Oval Beach.

If it’s too chilly outside, turn in early at the LGBT-owned Hidden Garden Cottages & Suites to cuddle up by your room’s fireplace

RELATED: Where to Eat in Saugatuck

Saugatuck Day Trip: Things to Do with One Day in Saugatuck

St. Joseph, Michigan

With a budding art scene, panoramic views of Lake Michigan, and several wineries to visit, St. Joseph, Michigan, is perfect for a romantic getaway.

This lakefront destination in Southwest Michigan was even named Michigan’s Most Romantic City by the Detroit Free Press and the Riviera of the Midwest by the Fine Living Channel. 

There are a variety of activities that are appealing to all types of couples. If you’re into the arts, consider visiting the Box Factory and Krasl Art Center. For the athletic couple, book a tee time at the Jack Nicklaus-designed Harbor Shores Golf Club. If you want to relax and indulge, visit the wineries along the Lake Michigan Shore Wine Trail.

Throughout your getaway, you can dine at several restaurants with waterfront views. Start your day with a latte along the Paw Paw River at Clifford’s Coffee Canal. Then grab lunch at Schu’s Grill, overlooking Lake Michigan in downtown St. Joseph. Finally, wind down your day at Plank’s Tavern on the Water, an upscale American restaurant right on the St. Joseph River.

The Inn at Harbor Shores is a great hotel for couples to stay at overnight. With a spa, indoor and outdoor pools, hot tubs, and modern rooms, this hotel provides luxury accommodations at an affordable rate. 

Recommended by Jackie Kanyolo, From Michigan With Love Blog

St. Louis, Missouri

St. Louis is a centrally-located first-rate destination for a Midwest romantic getaway at the center of a circle connecting Chicago, Indianapolis, Nashville, and Kansas City.

Whether your better half is an art, animal, food, culture, or history lover, St. Louis delivers brand-name recognition and a world-class experience without the crowds. You and your significant other will find plenty of things to do in St. Louis.

Watch the sunrise over the Mighty Mississippi from behind the Gateway Arch before ascending the tallest man-made monument in the nation for the best views in town.

Explore the Saint Louis Art Museum, Missouri History Museum, or St. Louis Zoo, all of which are admission-free attractions at Forest Park.

Also, instead of a romantic bouquet of cut flowers, stroll through the Missouri Botanical Garden, which is consistently recognized as one of the top public gardens in the world.

Then, take your honey’s taste buds on a trip around the world without leaving The Lou at City Foundry, where the Food Hall offers cuisine from every corner of the earth. Afterward, head to Clementine’s Naughty and Nice, a local ice cream parlor with boozy “naughty” scoops and G-rated (alcohol-free) “nice” scoops.

If your romantic getaway includes a Cardinals game, stay at the Hilton St. Louis, which provides great stadium views. Alternatively, book yourselves a suburban accommodation away from the hustle and bustle downtown at Le Meridien St. Louis Clayton.

It’s amazing what a few days away from work, homeownership, parenting, and pets can do to focus on and reconnect with your significant other, and St. Louis is the perfect place to rekindle that spark!

Recommended by Sage Scott, Everyday Wanderer

Stillwater, Minnesota

Nestled along the St. Croix River in the Minneapolis-St. Paul area, Stillwater, Minnesota, is a charming riverfront destination for a Midwest romantic getaway any time of the year.

In winter, glide together around an outdoor ice rink or get your hearts pumping by cross-country skiing or snowshoeing the local trails. Then, warm up with a private sauna session, a dip in the Hotel Crosby rooftop hot tub, or a snuggle before a flickering fireplace at one of the romantic bed and breakfasts. 

During the warmer months, cruise along the river on a romantic gondola ride, stroll through the mural-lined Union Art Alley, or bicycle across the historic lift bridge on a 4.7-mile loop trail connecting Stillwater to St. Croix County in Wisconsin. Then, lick one of Nelson’s Ice Cream’s heaping cones or another sweet frozen treat along the Stillwater Treats Trail to cool down.

When fall rolls around, pick apples and taste wines and ciders at Aamodt’s Apple Farm, see the colorful foliage from a hot air balloon, and throw axes (while sporting matching flannels) at the Lumberjack Axe Throwing Bar.

With over 100 locally owned boutique shops and restaurants, Stillwater’s historic downtown is a date-worthy destination in any season, making staying at the Hotel Crosby or the Lora Hotel particularly convenient. 

For a truly unique experience near downtown, book your romantic getaway at the Commander-South Bin, a grain elevator that has been renovated into a vacation rental. Though you’ll have to ascend 70 steps to the contemporary apartment, you’ll be rewarded with sweeping views of the historic downtown and the St. Croix River.

Traverse City, Michigan

Nothing says romance like a waterfront view, right? Grand Traverse Bay sets a scenic backdrop on a romantic getaway in Traverse City as you and your partner taste wines, dine, and stay overnight at Delamar Traverse City.

At this bayfront Traverse City hotel, take in the view from the floor-to-ceiling window in your room, a colorful Adirondack chair near the dock, or your dinner table while dining at Artisan Waterfront Restaurant & Tavern.

After a dinner of Lake Michigan-inspired cuisine paired with handcrafted cocktails or wine, unwind with a dip into the heated outdoor pool or indoor hot tub.

Beyond your stylish hotel, you’ll see panoramic bay views over the vineyards on Old Mission Peninsula. At Brys Estate Vineyard & Winery and Mari Vineyards, the scenic view is best enjoyed with a glass of chilled Riesling and a charcuterie spread. When the weather makes you want to head indoors, go wine tasting inside 2 Lads Winery’s tasting room.

Of course, the views are best from the water itself. Try stand-up paddleboarding, kayaking to breweries, or holding on tight to your partner as you ride across the waves on a jet ski! Most romantic of all? Watch the sun go down during a sunset sail on Grand Traverse Bay!

Wisconsin Dells, Wisconsin

The Wisconsin Dells is a great romantic destination in the Midwest for adventurous couples. In fact, there are lots of fun things to do in the Wisconsin Dells for adults. 

The best Wisconsin Dells resorts for adults — Kalahari, Wilderness, and Chula Vista — include water-park admission as part of the room rate. At these Wisconsin Dells water parks, take thrilling rides on waterslides designed for two people to ride together and sip cocktails together in one of the hot tub swim-up bars. 

Then, for some friendly competition, play mini golf, race each other at go-kart tracks, or even try axe throwing. Rather be on the same team? Build your communication and teamwork skills at an escape room or the interactive scavenger hunt Wizard Quest! 

Another interactive date idea is pottery painting at Polka Dot Pots. If you are staying at the Wilderness Resort, this is a great creative activity for couples! 

When it’s time to eat, the Wisconsin Dells has many unique restaurants and eateries for a fun date. You can share a family-style breakfast together at Paul Bunyan’s Cook Shanty or a meal from a food truck, sitting in the back of a converted Volkswagen camper at the Grateful Shed Truckyard.

Recommended by Kylie, Between England and Iowa

Ready to plan your next romantic getaway in the Midwest?

Are you and your partner passionate about wine? Then Traverse City is the perfect place to cozy up with a glass and take in the waterfront view.

Maybe you prefer a small-town vibe. If so, Saugatuck offers on-and off-the-water activities for two in a slower-paced locale.

Or, perhaps it’s the glitz of the Windy City at night that sparks romance on a weekend in Chicago.

Whether it’s a quiet escape or an exciting weekend for two, the romantic getaway you seek can be found in America’s heartland.

In this post, my fellow travel bloggers and I have recommended 13 destinations for romantic Midwest getaways.

For more ideas about where to go for your next romantic getaway in the Midwest, I encourage you to read my posts about Illinois, Indiana, Michigan, Minnesota, Missouri, and Wisconsin.

Read Related Articles

• 10 Magical Midwest Christmas Getaways
• Ann Arbor, Michigan Date Ideas
• Romantic Restaurants in Grand Rapids, Michigan
• How to Plan Your Dream Costa Rica Honeymoon (or Romantic Getaway)

Save this post to Pinterest on your romantic getaways, couples travel, or Midwest travel board!