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. It’s home to Destination Kohler, a five-diamond resort operated by the Kohler Company (yes, the brand best known for its plumbing products), and a perfect romantic escape for couples. You’ll want to book a stay at the American Club, a century-old 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 aplenty, from the aptly-named Lodge Restaurant set inside a cabin and 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 relaxation pools.

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 half a dozen roses and a private carriage ride. Bring your sweetheart to Original Murdick’s Fudge, which uses a recipe dating back to 1887. Walk 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 from 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 on display 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 combines German and French fare. You can also relax with a couples massage at the Galena Day Spa, which ends with chocolates and Champagne 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 hosts a cocktails 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 + Studio Winery for a tasting during the afternoon or live music on the 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 like pedaling a swan boat through the Veterans Park lagoon or taking in the views of the Milwaukee River while slurping oysters at Vault. Head to At Random Cocktail Lounge to share their Love Bowl and see why the place has been a date night staple since 1964. Stay downtown at Kimpton Journeyman Hotel for a package including a bottle of bubbly, chocolates and late checkout.

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’ three 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, a group of 26 wineries providing an opportunity to chat with the winemakers and taste their works. 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 which features 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. Toast to a great trip with a glass of bubbly and dessert at Gallery Bistro & Bar.

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

Reserve one of the five rooms at the Fleur-De-Lys Mansion, a 19th-century manor popular with honeymooners, and they’ll throw in free tickets to the nearby Missouri Botanical Garden. The 79-acre space features 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, where you can order steak and seafood a la carte or let the chef pick a four-course dinner with wine pairings.

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 stroll through the Pleasant Valley or Dufield Pond conservation areas. The area is full of farms, so depending on the season you can pick your own strawberries and raspberries from Heider’s Berry Farm or take a hayride to apple picking at All Seasons Orchard. 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 which offers large suites with a whirlpool tub, fireplace, balcony and 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 area 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 for you. If you prefer to be closer to the water, stay at the Oakwood Resort and explore the lake in a pontoon boat.

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 during the winter. 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.