Starting your romantic weekend in Millennium Park might seem surprising, but its variety captures what makes Chicago tick. The amazing architecture, gardens and art throughout the park create the perfect setting for a hand-in-hand stroll. Couples from around the word squeeze close to the shiny Bean (Cloud Gate) to get pictures with the reflection of Chicago’s outstanding skyline.
Couples who like to stay on the go conquer sightseeing and hunger during Bobby’s Bike Hike. The Bikes, Bites & Brews Tour is a four-hour jaunt with stops for deep-dish pizza, locally crafted beer, Chicago-style hot dogs and cupcakes. For couples that crave a hands-on experience, The Chopping Block offers cooking classes at their Merchandise Mart and Lincoln Square kitchens. Sign up for the Date Night: Two to Tango class and learn how to prepare the perfect empanada.
If you prefer to leave the cooking to the pros, linger over multiple courses at GT Fish & Oyster, a stylish River North eatery. Start with the caviar service for two followed by a selection from the raw bar, then share seasonal small plates. For a nightcap, a 42-page wine list spans the globe at City Winery, where artists from every genre reveal their talents to an appreciative room.
A cheery staff welcomes you to the River Hotel, which stands along the Chicago River and offers cozy rooms. For a more sumptuous experience, The Talbott Hotel in the Gold Coast balances Old World decor with polished service. After a luxurious sleep-in, brunch at Yolk on East Ohio Street promises veggie-packed omelets, griddle specialties and juicy pot roast sandwiches.
Shopping along Armitage Avenue and Halsted Street in Lincoln Park winds through boutiques that specialize in high-end handbags and earth-friendly clothes and accessories. Stay in the neighborhood for an early dinner at Cafe Ba-Ba-Reeba!, where tapas makes it fun to order a few dishes to share.
Fall brings a fresh season of performances from the Chicago Symphony Orchestra, where well-coiffed couples soak in the marriage of craftsmanship, musicianship and acoustics. This fall, the first concert will re-create the orchestra’s debut performance from 1891, reminding us all that the best loves are timeless.
Eden Laurin is a managing partner at The Violet Hour in Chicago’s Wicker Park. The stylish bar reinvents Pre-Prohibition cocktails and pays tribute to simpler times—cell phone usage is banned inside the lounge. One of the city’s most buzzed about venues, The Violet Hour won the 2015 James Beard Award for Outstanding Bar Program. Laurin shares these suggestions for a romantic weekend in her favorite city.
1. The Museum of Contemporary Art along the Magnificent Mile always strikes up a conversation.
2. Grab two counter stools at Dove’s Luncheonette in Wicker Park and share some Mexican soul food.
3. Take a Cocktail 101 class at the Violet Hour, which reveals the stories behind many vintage drinks.
4. Join the crowd for dinner at Big Star, a boisterous Wicker Park taqueria known for its tacos and margaritas.
5. Spend an evening at Hubbard Street Dance Chicago, a contemporary dance company in the Loop.
Every autumn, busy couples in need of some serious downtime guide their cars up and down hilly, forested scenic drives that wind in and around Galena, a historic small town in the state’s northwest corner. After checking in at the Jail Hill Inn, meet other travelers at the inn’s wine-and-cheese reception to compare notes on the activities in store.
Canoe and kayak trips down the Galena River quietly showcase the beauty of the hills’ red and gold foliage. Fever River Outfitters offers easy trips with shuttle service and picnic lunches. Or, if you’d rather dine in town, Otto’s Place is a popular choice for lunch.
Rare books, creative salsas and handmade jewelry are just some of the offerings in the Main Street stores, where it’s easy to spend a few hours shopping. History buffs like to explore the nearby Ulysses S. Grant Home, which stands furnished as it was 150 years ago and includes docent-led tours. For dinner, try One Eleven Main, a popular eatery that keeps it fresh by partnering with regional farmers and food purveyors.
A three-course gourmet breakfast at the inn fuels the next food-filled day ahead. On the must-try list: a seasonal cooking class with the Breakfast Diva, Susan Steffan, who launched her funny, easy lessons after a stint on the Food Network’s Holiday Baking Championship. Tastings of each dish are part of the hands-on class.
Scenic fall drives offer a little quality time before an afternoon at Blaum Bros. Distilling Co. Tours break down how local grains become craft spirits. Also find some time to enjoy a couples’ massage at the Inn at Irish Hollow, one of the area’s most romantic getaways.
For pretty views of the Mississippi River, head to Chestnut Mountain Resort for dinner at the Sunset Grille. The white-tablecloth setting exudes class, and the menu ranges from cracker-thin pizzas to filets and lobster. End the day at Frank O’Dowd’s Irish Pub, where live entertainment plays to a spirited crowd on the weekends.
Matthew Carroll brought a 135-year-old county jail back to life as the Jail Hill Inn, Galena’s newest luxury inn. The property is romantic through and through, from guestrooms appointed with chocolates and champagne to many cozy nooks for some quiet time. Overlooking downtown, the inn is an easy stroll from Galena’s bustling Main Street. Innkeeper Carroll offers these suggestions for couples visiting the area.
1. Share a meal at Fritz & Frites. Their salmon with lingonberry and pommes frites with truffle salt are legendary. And the apple strudel with cinnamon ice cream...OMG!
2. Go to Miss Kitty’s Grape Escape for live music, anything from bluegrass to classic rock. And they have great martinis.
3. See our “driftless region” from above in a hot air balloon. Galena on the Fly offers a once-in-a-lifetime experience.
4. Hang out on the deck at Galena Cellars Vineyard & Winery. Their sparkling Mimosa is a great celebration wine!
5. Browse the art galleries downtown. Carl Johnson is a staple here—his watercolors capture Galena’s amazing architecture.
Just an hour west of Chicago, downtown St. Charles preserves a historic vibe and a sense of genuine hospitality. Arched bridges span the beautiful Fox River and invite couples to unwind for a weekend of outdoor fun and antiquing.
Rare antiques, collectibles and an old-fashioned soda fountain give couples a chance to browse and buy as they walk down memory lane. Seafood lovers craving the freshest catch can’t miss E&S Fish Company. Simple, beautifully plated salmon, sea scallops and jumbo shrimp come served with perfectly cooked veggies and sauces.
The annual Jazz Weekend (September 8–11) fills downtown with a celebratory feel and plenty to see. Musicians and vendors give couples a chance to stroll hand-in-hand and enjoy pretty fall days. Make reservations at Francesca’s by the River for a romantic Italian dinner. Housemade pastas shine here, and a killer crème brûlée tempts.
Plan to stay at the historic Hotel Baker, a 53-room boutique lodging along the Fox River. Built in 1928, this hotel with an Old World feel is listed on the National Register of Historic Places, and its cheerful staff ensures you feel special throughout your stay.
Sunday brunch at Town House Books & Cafe feels just right for book lovers and, really, anyone who appreciates good food. Raspberries, cream cheese and bananas stuff the Tequila Sunrise French Toast, and a hot avocado tuna melt combines comfort food and healthy freshness.
You’ll find that one person’s trash is another one’s treasure at the monthly Kane County Flea Market, held during the first weekend of each month from March through December. Hard-core flea fiends could easily spend both days here, and use Sunday afternoon to barter with dealers eager to move their wares.
New to the area, the Finery & Blacksmith Bar calls itself “an ode to the American table.” But most couples would agree that the perfectly prepared ahi tuna appetizer and pressed pork belly with acorn squash puree don’t look much like the tables they’re used to. And that’s a good thing. After dinner, catch a show at the Arcada Theatre, an intimate venue known for its VIP treatment and steady lineup of big-name rock and comedy acts.
Rowena Salas is general manager of the historic Hotel Baker, located along the banks of the Fox River in St. Charles. The hotel is a popular wedding destination, with a two-tier ballroom and riverfront gardens. Visitors are able to stroll from the Main Street hotel to popular area attractions. Salas suggests adding these favorites to the itinerary.
1. Rent a pair of bicycles at Sammy’s Bikes and head out on the Fox River Bike Trail.
2. ROX City Grill, the restaurant at Hotel Baker, is known for its great steaks, savvy wine pairings and weekend piano music.
3. Catch a show at Steel Beam Theatre, a (four-rows tiny!) theater known for its excellent community productions.
4. Try something new at Shakou Sushi, popular for its Asian fusion dishes.
5. Check out Rocket Fizz Soda Pop & Candy Shop, a fun new place to get a sugar rush.
There are countless ways to experience the best of Chicago during the winter mon...