If you’re looking to celebrate Valentine’s Day outside of Chicago but don’t want to deal with the hassle of planning a trip, we’ve got you covered. The Midwest is filled with charming towns that feel just like scenes from a Hallmark movie, and we know a couple of places that will meet your needs.
From a cozy bed and breakfast located at a winery to a modern treehouse near one of Illinois’ most popular state parks, we have gathered three idyllic destinations within a three-hour drive of Chicago—perfect for a Valentine’s Day getaway.
Romance Close to Home in Roselle — 1-Hour Drive from Chicago
For those who prefer a Valentine’s Day getaway closer to home, the suburbs offer escapes filled with charming adventures—specifically, Roselle.
Where to stay:
Experience a luxurious stay at Lynfred Winery B&B in Roselle, where you can choose from four beautiful guest suites that set the mood for a cozy Valentine’s Day.
Where to dine:
One of Illinois’s oldest and largest continuously operating wineries, Lynfred Winery, is also an ideal place for dinner. They offer personalized wine and cheese tastings, and for an upscale dining experience, savor fresh, seasonal cuisine paired with an extensive wine list at 1913 Restaurant and Wine Bar.
Escape to Starved Rock Country — 2-Hour Drive from Chicago
With the scenic backdrop of Starved Rock State Park, the Illinois River Valley is ideal for couples seeking an adventurous Valentine’s Day getaway. Here, you will find serene hiking trails, canyons, and waterfalls just a short drive from the city.
Where to stay:
Stay at the newly opened Treehouses at Starved Rock. These spacious three-bedroom accommodations, nestled on the edge of Starved Rock State Park, offer the perfect retreat for couples looking for a secluded getaway.
Where to dine:
Head to Millstone Bakery in La Salle for freshly baked goods in the morning, or spoil yourself with a farm-to-table meal at the Lone Buffalo in Ottawa. After your hike, unwind with a glass of sparkling wine at the August Hill Winery Tasting Room in nearby Utica.
Galena’s Romantic Charm — 3-Hour Drive from Chicago
Visit Galena for a picturesque weekend full of small-town charm. Stroll along Historic Main Street, which is filled with boutiques, art galleries, and locally owned restaurants. Enjoy a playful evening goat trek at Hoof It Goat Treks, complete with baby goats and a cozy bonfire under the stars.
Where to stay:
Relax at Ulysses Suites for a cozy stay in the heart of downtown Galena. Housed in the beautifully renovated J.G. Schmohl building—once home to the historic Grant Hotel from 1895 to 1932—this luxury vacation rental combines modern comfort with historic elegance.
Where to dine:
Start your day at Galena Bakehouse, a charming grab-and-go bakery on Historic Main Street, where owners Geoff and Alex craft gourmet pastries, empanadas, and lunch options using locally sourced, made-from-scratch ingredients. We recommend Fried Green Tomatoes, known for its rustic Italian dishes, award-winning wine list, and signature fried green tomatoes for dinner.
Visit Galena Cellars Vineyard, one of Illinois’ oldest family-operated wineries, to sip on award-winning wines while taking in spectacular vineyard views and learning about the winemaking process.