The most romantic getaways from Chicago for couples

Driving time from Chicago: Two and a half hours

Just west of Sheboygan, Wisconsin sits the small village of Kohler, headquarters of the company of the same name best known for its plumbing products. That might not sound like the perfect romantic escape, but it’s also home to the American Club, a century-old, five-diamond resort luxury hotel that’s brimming with both historic charm and modern amenities. Start your morning with Yoga on the Lake before embarking on an adventure around a 500-acre wilderness preserve. Food and beverage options are plentiful, from a five-course tasting menu at The Immigrant Restaurant to the casual Horse & Plow pub to a quaint greenhouse-turned-cafe. Of course, no getaway would be complete without a visit to Kohler Waters Spa, where you can pamper yourself with rejuvenating massages, hydrotherapy treatments and dips in a relaxation pool.

Driving time from Chicago: Six and a half hours

The abundance of natural beauty and car-free streets make Mackinac Island a popular destination for weddings. See why by booking a romance package at Cloghaun Bed and Breakfast, which includes flowers and a private carriage ride. Bring your sweetheart to Original Murdick’s Fudge to enjoy recipes dating back to 1887. Walk or bike the eight miles around the island to take in the views, heading to the west side in time to see the sunset. You can get an even better view from the water during a sunset cruise with Great Turtle Kayak Tours.

Driving time from Chicago: Four hours

Spanning 300 miles of shoreline, the peninsula between Green Bay and Lake Michigan boasts numerous hiking trails and perfect spots to watch both the sunrise and sunset, plus spectacular stargazing at Newport State Park. Visit Door Peninsula Winery, where you can try some of their 60 varieties of wines and ciders, and pick up a bottle of your favorite to enjoy at one of the area’s many cozy bed and breakfasts like Eagle Harbor Inn, where the suites are outfitted with a fireplace and giant whirlpool tub.

Driving time from Chicago: Three hours

Book a romantic getaway package at Goldmoor Inn and they’ll have a dozen roses waiting for you in your room. Rent a tandem kayak from Nuts Outdoors and spend two hours paddling on the Galena River, starting against the current so you can relax and float on your way back to the dock. Head back to the hotel for a bath in your two-person whirlpool tub, then grab dinner on Galena’s historic Main Street at Fritz and Frites, which blends German and French fare. You can also relax with a couples massage at the Galena Day Spa, which ends with chocolates and a drink in your private relaxation room.

Driving time from Chicago: One and a half hours

Chicagoans have been escaping to Lake Geneva since the late 19th century and the city is home to numerous resorts and vacation rentals. Get a sense of that history at Maxwell Mansion, which was built as a summer home in 1855 and boasts a cocktail bar with outdoor bocce ball courts and fireplaces. For a luxurious retreat, book a room at the Grand Geneva Resort & Spa, a popular wedding venue that features skiing, golf, indoor and outdoor pools, and a spa. Stop by Geneva Lake Distilling + Winery for a tasting during the afternoon or live music on weekends.

Driving time from Chicago: One and a half hours

Milwaukee is best known for beer, and hop lovers can share their passion with brewery tours or pints paired with cheese curds and sausages. There are plenty more conventionally romantic attractions depending on the season like pedaling a swan boat through the Veterans Park lagoon, ice skating at Red Arrow Park or taking in the views of the Milwaukee River while slurping oysters at Vault. Head to At Random Cocktail Lounge to share a Love Bowl and see why the place has been a date night staple since 1964. Book a couples getaway at The Pfister Hotel downtown and they’ll have macarons and a chilled bottle of Champagne waiting in your room.

Driving time from Chicago: Two and a half hours

Madison has a fantastic food scene, including plenty of romantic destinations like French farm-to-table spot L’Etoile and the lakeside bistro Sardine. You can also enjoy the city’s five lakes by visiting one of Madison Boats’ four locations and renting a tandem kayak or canoe. After sharing some time on the water, retire to your suite at Mansion Hill Inn, where you can warm up in front of the fireplace. Sweeten your time together with a visit to Gail Ambrosius Chocolatier, which offers pairing suggestions for beers to accompany truffles with varieties including lemongrass with ginger and shiitake mushroom.

Driving time from Chicago: Five hours

Spend the day walking along the beach and taking in spectacular views of Lake Michigan from the bluffs at Sleeping Bear Dunes. Then visit the Traverse Wine Coast to chat with the winemakers at more than 50 wineries and taste their products. Pick up a bottle and head back to the Glen Arbor Bed & Breakfast, where you can book a romantic package and have a bouquet of flowers and a box of organic truffles from Grocer’s Daughter Chocolate waiting for you.

Driving time from Chicago: Three hours

Created in 1970, Robert Indiana’s steel “LOVE” sculpture is one of the most iconic pieces at the Indianapolis Museum of Art at Newfields, which also hosts works by Rembrandt and ancient sculptures from around the world. While you’re there, stroll through The Garden to explore 52 acres of winding paths, fountains and plants. Imagine you’ve been transported to Venice when you book a gondola ride on the city’s Central Canal, a popular option for proposals and anniversaries. Share some farm-to-table fare and cocktails at Bluebeard—a hotspot during patio season.

Driving time from Chicago: Three hours

Wisconsin Dells is best known for family-friendly fun, but the city also can provide a fun getaway without the kids. Skip the waterpark resorts and head to Sundara Inn & Spa to soak in one of their many heated pools. It goes beyond the usual couples massages to offer a full menu of services, including baths and facials in a spa suite for two warmed by a fireplace. Put together a picnic and spend the day at Devil’s Lake State Park, which offers nearly 30 miles of hiking trails through a landscape shaped by a glacier.

Driving time from Chicago: Three hours

Grand Rapids is a haven for beer fans, offering plenty of tours and tastings for couples who share a love of hops plus an opportunity to walk through town with a drink thanks to its numerous refreshment areas. Even if that’s not your idea of romance, the city has plenty else to do. Take a stroll through the Frederik Meijer Gardens & Sculpture Park, enjoying the tranquility of the Japanese garden and the vibrant birds and orchids in the tropical conservatory. Book a sightseeing cruise on The Grand Lady riverboat or get a couples massage at Celeste Salon & Spa at the Amway Grand Plaza and soak in the views of the river from your room.

Driving time from Chicago: Three and a half hours

The home of Indiana University isn’t just for sports fans. Oliver Winery, the largest winery in Indiana, offers a taste of romance with picnic packages from April to October and igloos you can book during the winter. Pick out a favorite bottle to take back to Century Suites, where you can book a room with a fireplace and whirlpool tub. For some outdoor fun, head to Monroe Lake, which offers hiking trails and docks where you can rent a kayak for two.

Driving time from Chicago: One hour

Share your love of the outdoors by taking a dip at West Beach and then strolling along the lakefront at Indiana Dunes National Park. Equally impressive is the Indiana Dunes State Park, where you can take the 3 Dune Challenge and trek 1.5 miles up a series of hills to see some spectacular views. You can grab dinner right on the beach at The Pavilion, a popular wedding destination, then head back to your room at the Songbird Prairie Inn and Spa to soak your tired muscles together in a whirlpool bath.

Driving time from Chicago: Five hours

Spend a day strolling through the 79-acre Missouri Botanical Garden to see one of the largest Japanese gardens in North America plus an impressive sculpture collection. Take in the city’s skyline at sunset with a ride on The St. Louis Wheel, where you’ll go 200 feet up in a fully enclosed gondola. Then share a romantic meal at Annie Gunn’s—you can order steak and seafood a la carte or let the chef pick a four-course dinner with wine pairings. Spend the night at the Royal Sonesta Chase Park Plaza St. Louis, which has its own movie theater and an outdoor fireplace.

Driving time from Chicago: Two hours

Outdoorsy couples should head to Starved Rock State Park to take in dramatic waterfalls along the 13 miles of hiking trails. Those looking for a bit more relaxing sightseeing can book a trolley tour, which depending on the time of year can provide opportunities to spot bald eagles, take in the fall colors or jaunt between the waterfalls. Book a stay in one of the new treehouses right on the edge of the park; they're equipped with fireplaces and gorgeous views. After a day out, share a farm-to-table dinner and some beer at The Lone Buffalo. 

Driving time from Chicago: One and a half hours

Best known as the filming location for Groundhog Day, the historic town is filled with nostalgic charm. Take a walking tour of spots featured in the movie including the Woodstock Opera House, which hosts concerts, dance performances and art exhibits. Enjoy some natural beauty with a walk through the Pleasant Valley or Dufield Pond conservation areas. The town is also full of farms, so depending on the season you can pick your own strawberries and raspberries from Heider’s Berry Farm or blueberries at McCann Berry Farm. Stay the night at the Cherry Tree Inn B&B, which can have flowers, chocolates, wine and cheese ready for you and arrange a private dinner for two.

Driving time from Chicago: One hour

Travel back in time to this picturesque town known for the numerous festivals hosted in its historic downtown area, which you can explore by walking down cobblestone pathways lined with flowers. Highlights include the Chocolate Fest in May and Strawberry Fest in June, but it’s worth a visit any time to check out its quaint shops and enjoy some wine, cheese and charcuterie at Broken Earth Winery. For a real taste of history, share dinner at The Village Tavern: Established in 1847, it’s the oldest restaurant in continuous operation in Illinois.

Driving time from Chicago: Two and a half hours

Stay right on the shore of Lake Michigan at Blue Harbor Resort & Conference Center, a popular wedding destination that offers large suites with a whirlpool tub, fireplace and a balcony or patio plus a spa where you can get an hour-long couples massage. Walk along the beach or hike along the sand dunes at Kohler-Andrae State Park, then share a romantic dinner at Lino Ristorante Italiano, which uses local organic products in decadent dishes like pappardelle with slow-roasted lamb ragu and lasagna made with Italian sausage. 

Driving time from Chicago: Two and a half hours

Located between Syracuse Lake and Lake Wawasee, Syracuse offers plenty of opportunities for waterfront fun. Walk or bike through trails that will take you through wetlands and into the downtown area while providing some stunning views, and then grab a hand-breaded cod sandwich and a hurricane on the water at Channel Marker. Book the romantic getaway package at Brook Pointe Resort and your room will be decorated with candles and rose petals, and there will be a chilled bottle of bubbly waiting. If you prefer to be closer to the water, stay at the Oakwood Resort, which also offers hiking routes and biking paths around the 27-acre property.

Driving time from Chicago: One hour

The city on Lake Michigan is a haven for outdoor enthusiasts year-round thanks to its many beaches, parks and hiking trails. Get a private sailing lesson from Sail Away Charters, whose two-hour outings are regularly used for anniversaries or marriage proposals. Couples who like to share thrills can navigate the bridges and ziplines at Boundless Adventures during the summer or hit the slopes at Wilmot Mountain in the wintertime. Get dressed up for a day of jousting, music and wild costumes at the Bristol Renaissance Faire, then share an intimate meal at old school Wisconsin supper club Hobnob.