The 10 most romantic getaways from Chicago

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: 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. You don’t need any experience paddling to rent a tandem kayak from Galena River Outfitters and spend a few hours on the Galena River taking in the scenery and wildlife. 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: 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 more than half a million blooms. 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 Pastry Bar.

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

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: 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: 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 a rainforest-themed conservatory. 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 Vin de Set Rooftop Bar & Bistro, which serves French fare made with ingredients grown in their own hydroponic greenhouse.

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 you’ll also get a free ride on their tour boat.

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 40 wineries where you’ll get 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.