4 Romantic Weekend Getaways Near Chicago

Baker House, Lake Geneva

It’s winter in Chicago, which means if you’re like us — and everyone else in this city — you’re ready to get away. This Valentine’s Day, why not hit the road with that special someone for a cozy and romantic weekend escape?

Here are four hideaways where you can retreat and recharge, all far enough from Chicago that you feel sufficiently “away” from home without facing too long of a drive.

The Steamboat House: Galena, Illinois

605 S. Prospect, Galena, Illinois, 815-777-2317

romantic weekend getaways: The Steamboat House
Photo courtesy of The Steamboat House.

Ulysses S. Grant once lived in Galena, along the banks of the Mississippi, when river boats rolled up and down, lending a lively air to this relatively small town. Galena still relies heavily upon visitors, though few now arrive by water.

All along the river are many historic homes, updated to be comfortable B&Bs, many accoutered handsomely with antique furnishings that bring you back to the nineteenth century, all cushioned by twentieth-century comforts.

The Steamboat House was built in 1855 by Daniel Smith Harris, who launched the first riverboat from Galena. Receptions were held at his house for nineteenth-century notables including Grant and Susan B. Anthony. Now, it’s a wonderfully restored old residence with nine comfortable bedrooms, seven fireplaces, a billiard parlor, and a big dining room where you can take breakfast and, to whatever extent you want, get to know other guests. Peek into the backyard and you’ll spot the entrance to the rough-hewn root cellar that was once packed with ice in the winter to keep vegetables fresh until the next growing season.

romantic weekend getaways: Steamboat House (billiard)
Photo courtesy of The Steamboat House.

Eighty-five percent of Galena’s downtown buildings are on the National Register of Historic Places. Downtown Galena is zoned to prohibit franchises, so there are many small shops offering sometimes quirky wares; we especially like Root Beer Revelry, a store specializing in vintage soda, and For Bare Feet, offering unusual socks. For fine dining, One Eleven Main is an excellent place to taste local food and drink (yes, they do produce beer and wine in this part of Illinois).

The Dearborn Inn: Dearborn, Michigan

20301 Oakwood Blvd., Dearborn, Michigan, 313-271-2700

romantic weekend getaways: The Dearborn Inn
Photo courtesy of Marriott.

The Dearborn Inn was designed by Albert Kahn, “the architect of Detroit,” and commissioned by Henry Ford. The Inn originally accommodated visitors flying into nearby Dearborn Airport, and it’s also on the National Register of Historic Places. In 2009, AAA recognized it as one of the top 10 historic hotels in the country.

The Dearborn Inn has many rooms, but for a more romantic experience, there are five colonial-style guest houses named after some of Ford’s favorite Americans, including Patrick Henry and Edgar Allen Poe.

romantic weekend getaways: Dearborn Inn dining room
Dining room at The Dearborn Inn (Photo by David Hammond.)

Dearborn was once the thriving automotive capital of the world, the driving force behind the “Arsenal of Democracy” that boomed during World War II. Like all of Detroit’s metro area, Dearborn has fallen on hard times, but this is not the apocalyptic, post-rapture no-man’s-land sometimes portrayed on television. Detroit is a city on the remake, and it’s one of the richest Middle Eastern dining zones in the country. With the highest concentration of Arab Americans in the United States, it offers a truly spectacular selection of foods from the Arab World, with restaurants like Al Ameer, which in 2016 was Michigan’s first recipient of the James Beard American Classics award. Dearborn’s Arab American National Museum hosts a series of walking food tours that provide an excellent introduction to the city’s culinary offerings.

Baker House: Lake Geneva, Wisconsin

327 Wrigley Drive, Lake Geneva, Wisconsin, 262-248-4700

romantic weekend getaways: Baker House
Photo by Peter Harasty Studio.

In a town of romantic B&Bs, Baker House stands alone. Built on the shoreline in 1885, affording expansive views of Lake Geneva, Baker House is a Victorian gem, with a spacious and comfortable bar, dining areas that pull through the antique theme, and sitting rooms where guests and other visitors can relax in wing-back chairs and plush settees. There is nothing hip and happening about Baker House, and guests like it that way: It’s elegant and unapologetically old-timey.

Baker House is also, let us say, idiosyncratic. There’s a hat rack near the entryway where you should pick up a vintage hat to wear throughout the evening in a kind of casual masquerade.

The Ringmaster’s Roost is a bar, with big-top accoutrements, staffed by mixologists who know what they’re doing, serving classic cocktails but also innovative signature drinks.

The dining room, wood-paneled and plush, serves from a large menu throughout the day. Romantic dinners-for-two are available, with what are described as “a selection of seduction menu items.” For the Sunday morning-after, brunch features unlimited champagne.

For a special dinner offsite, head to Hunt Club Steakhouse for killer steaks and a world-class wine list; Sopra Bistro, for farm-to-table food in a more urban setting; or Oakfire, for authentic Neapolitan wood-fired pizzas in a lively, festive atmosphere. For healthy, seasonal breakfasts and lunches, Simple Café is a favorite.

Eagle Harbor Inn: Door County, Wisconsin

9914 Water St. S, Ephraim, Wisconsin, 920-854-2121

romantic weekend getaways: Eagle Harbor Inn
Photo courtesy of Eagle Harbor Inn.

Accommodations in Door County villages like Sister Bay and Ephraim are picture-perfect embodiments of “cozy.” We stayed at Eagle Harbor Inn, where innkeeper Natalie Neddersen told us, “We never buy furniture from institutional supply houses. All our furniture is residential. We want you to feel like you’re in someone’s home. Cozy.”

Of course, the coziness factor is multiplied when you bring that special someone, but you probably already knew that. Few people go to Door County solo.

There’s quite a lot to do in Door County, even in the winter. You can visit a distillery and several breweries. Local restaurants tend toward the Nordic, none more so than Al Johnson’s Swedish Restaurant, famous for goats grazing on the roof and colorfully costumed Swedish maidens serving local faves like pytt i panna, roast beef hash, and Swedish pancakes and meatballs (of course!).

If you’re feeling in a wintry mood, consider taking an ice breaker through Death’s Door and over to Washington Island. After experiencing that kind of cold, getting back to cozy will never feel better.

romantic weekend getaways: Door County ice breaker
Ice breaker en route to Washington Island (Photo by David Hammond.)


David Hammond is Dining and Drinking Editor at Newcity and contributes to the Chicago Tribune and other publications. In 2004, he co-founded LTHForum.com, the 15,000 member food chat site; for several years he wrote weekly “Food Detective” columns in the Chicago Sun-Times; he writes weekly food columns for Wednesday Journal. He has written extensively about the culinary traditions of Mexico and Southeast Asia and contributed several chapters to “Street Food Around the World.”

David is a supporter of S.A.C.R.E.D., Saving Agave for Culture, Recreation, Education and Development, an organization founded by Chicagoan Lou Bankand dedicated to increasing awareness of agave distillates and ensuring that the benefits of that awareness flow to the villages of Oaxaca, Mexico. Currently, S.A.C.R.E.D is funding the development of agave farms, a library and water preservation systems for the community of Santa Catarina Minas, Oaxaca. 


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