Romantic Getaways for Chicago Couples

Take a break without the kids at one of these nearby destinations.

Nothing says “I love you” as much as spending time together. Plus, taking a break from chores and carpooling is a total bonus too. Plan a Midwest weekend getaway with your love.

Enjoy some one-on-one time (like before the children came along). Even if you want to postpone traveling at the moment, remember these relaxing destinations that will slow you down enough to feel your hearts flutter.

Note: We’re updating our website as quickly as we can, but changes may occur due to COVID-19. Please double check before heading out for the most updated information on safety precautions, vaccine requirements, travel advisories and any last-minute closings. Stay safe!

New Buffalo, Michigan

Photo credit: Goldberry Woods
  • Drive from Chicago: 1 hour and 30 minutes

Just hop over the Michigan state line and you’ll be on the Southwest Michigan coast, which Travel + Leisure rated as one of the “50 Best Places to Travel to in 2022.” Winter offers opportunities to fat-tire bike, snowshoe and cross-country ski. You’ll find the Lake Michigan Shore Wine Trail and gobs of tasty restaurants to try. The Stray Dog Bar + Grill is a perennial favorite. The cozy ambiance at Brewster’s Italian Cafe is as delightful as their seasonal pastas, salads, pizzas and desserts.

Stay at Goldberry Woods in nearby Union Pier. This family-run, micro-farm bed and breakfast serves up the love. During Valentine’s week, chocolately farm-to-table scratch breakfasts will be served directly to the rooms, where you’ll also find fresh roses. Soak in the double jacuzzi tub and relax by a gas fireplace. The outdoor pool and hot tub are also enclosed for a warm winter dip. Check their website for 2 Plus Tuesday and 20% off promotion details.

Milwaukee, Wisconsin

Photo credit: Pabst Mansion/Visit Milwaukee
  • Drive from Chicago: 1 hour and 30 minutes

What could be more romantic than a Valentine’s Day vow renewal? Hold your ceremony at the Pabst Mansion in Milwaukee. Elegant services at the historic venue are available on Feb. 13-14.

You can find a host of James Beard-recognized restaurants in Milwaukee. Or if beer, cheese curds and custard are more your thing, seize the opportunity to enjoy those. Lakefront Brewery is known to run some of the most hilarious brewery tours. Afterwards, dine in their German-style beer hall and see if you can hear your cheese curds squeak.

Kopp’s Frozen Custard is a Milwaukee classic. Check the website for a Flavor Preview of the deliciousness to come. Creative souls will adore Saint Kate- The Arts Hotel. Reserve a room designed by a local artist and be immersed in a unique, inspiring environment.

French Lick, Indiana

Photo credit: Visit Indiana
  • Drive from Chicago: 5 hours

Fall in love all over again at the French Lick Resort. Free Experience Designers can help make your visit extra special. Whether it’s for Valentine’s Day, a birthday, anniversary or proposal, the Experience Designers can arrange everything from horseback rides to dinner reservations and spa time.

West Baden Springs Hotel’s Valentine’s Day package includes a multi-course meal and chocolate-covered strawberries. Check the events calendar for mixology courses, and food and beverage tastings.

Lake Geneva, Wisconsin

Photo credit: The Ridge
  • Drive from Chicago: 1 hour and 30 minutes

A quick drive to Lake Geneva can provide a refreshing change of scenery. Take a winter hike at Kishwaketoe Nature Conservancy. Set your hearts aflutter on a winter zipline with Lake Geneva Adventures. Zipping through the snow-covered canopies can be quite exhilarating! If shopping is more your speed, create your own customized candle scent together at The Candle Mercantile. Weekend reservations recommended.

Cook up a gourmet dinner with your sweetheart in a hands-on class with the Lake Geneva School of Cooking  Stay at The French Country Inn on Lake Como and savor a romantic meal at Savoy. The Grand Geneva Resort features ski hills, a spa, and even Valentine’s Day package with a helicopter ride. Talk about sweeping off your feet!

The Geneva National Resort offers an Overnight Igloo Package, where you can dine in your own private, heated, illuminated snow globe. Indulge in appetizers, beverages and smokehouse favorites as you look out into the snowy scenery.

Elkhart Lake, Wisconsin

Photo credit: Osthoff Resort
  • Drive from Chicago: 2 hours and 25 minutes

The Osthoff Resort is a AAA Four Diamond resort located only a few hours away from Chicago. The lovely, all-suite hotel provides plenty of space to lounge around together so you can reconnect your orbit. Relax at the award-winning Aspira Spa featuring healing treatments and SpaSuite Experiences, which offer couples their own private environment to zen out together. Masks are required in public areas for both guests and associates.

Galena, Illinois

Photo credit: Blaum Brothers Distillery/Illinois Office of Tourism
  • Drive from Chicago: 2 hours and 40 minutes

Galena is not that far from Chicago, yet it feels like going back in time. This quaint little town with a historic downtown is perfect for a cozy winter stroll peaking inside shop windows. Snuggle up at Eagle Ridge Resort and Spa. Stay Feb 18-21 to enjoy Winter Carnival Weekend. Watch the Hot Air Balloon Glow from the warmth of a crackling bonfire.  

Warm up with some bourbon, gin, vodka or rye at Blaum Bros. Distilling Co., a hip distillery with fun cocktails and tours. Or clink glasses of vino at Galena Cellars Vineyard. It’s impastable not to love Vinny Vanucchi’s Little Italy, an authentic family bistro with made-from-scratch Italian delights.

St. Joseph, Michigan

Photo credit: Amber Kiel
  • Drive from Chicago: 1 hours and 35 minutes

Experience “Romance on the Boulevard” at The Boulevard Inn & Bistro in St. Joseph, Michigan. Located atop a bluff in downtown St. Joseph, the package includes overnight accommodations in a suite with a chilled bottle of champagne, fruit and cheese basket, Kilwins chocolates and a dozen long-stem red roses waiting for you. Masks are required in public areas.

Spend the afternoon sipping wines on the Lake Michigan Shore Wine Trail. Then dine at The Lakehouse, voted to have one of the best views while you eat in Michigan.

Kohler, Wisconsin

Photo credit: Kohler Co.
  • Drive from Chicago: 2 hours and 14 minutes

Stay at the historic American Club and enjoy the five-star, five-diamond service. Be greeted by smiling doormen tipping their top hats and savor a delicious dinner in an elegant setting at The Wisconsin Room. Chocolate lovers will be enamored with the artistic decadence of Kohler Chocolates.

Yoga on the Lake is a great way to stretch and get the stress out. Spin classes, tennis and snowshoeing are available too. You also simply can’t miss the Kohler Waters Spa, a tranquil retreat both men and women truly enjoy. Their body treatments, facials and massages are the heavenly self-care you definitely deserve.

Want a closer to home option? There are Kohler Waters Spas in Burr Ridge and Lincoln Park too. Now through the end of February, all three locations are offering a Peppermint Mocha Massage, Peppermint Mocha Pedicure and a Peace and Joy Gemstone Facial. Kohler Chocolates are now available in Lincoln Park too (see store for Valentine’s Day specials).

Shawnee Hills of Southern Illinois

Photo credit: Illinois Office of Tourism
  • Drive from Chicago: 5 hours

Head south for rolling hills, a touch of added warmth, outdoor activities and the Shawnee Hills Wine Trail. The sheer beauty of the Garden of the Gods will make your hearts skip a beat. Hike to some of the most stunning views in the Midwest, then hit the wine trail. Alto Vineyards is Southern Illinois’ oldest, most award-winning winery. Feel the romance of Italy at Blue Sky Vineyard’s Tuscan-inspired winery.

Stop at the Peachbarn Winery & Café for a local, seasonal menu served in a restored barn overlooking a peaceful pond. You’ll find authentic Swedish cuisine, appetizers, flatbreads, soups and deserts. Then relax in your own private hot tub at Shawnee Forest Cabins. These new log cabins are the closest to Garden of the Gods.


Photo credit: Jared Powell Photography/Fairmont Chicago

You can also have a romantic staycation right at home! Chicago boasts so many fabulous hotels, many offering even more reasons to adore them with seasonal specials. This winter, Fairmont Chicago introduced the Fairmont Lodge, which helps you create warm memories around indoor fire pits. Available from Wednesday to Sunday evenings, fire pit experiences can include signature cocktails, s’mores, fondue or charcuterie. Reservations required.

Sleep in at Swissotel Chicago, steps away from Navy Pier and the Mag Mile. Take advantage of the Romance Package and indulge in chocolate-dipped strawberries, champagne, breakfast for two and 2pm check out. Swim Under the Stars at The Langham, Chicago, where you can savor 2-hours private use of Chaun Spa’s pool along with a $100 food and beverage credit for poolside eats. This special overnight package is available until the end of 2022. The Langham also offers a lovely afternoon tea. Swoon over the Valentine’s Day Tea, available Feb. 11-13.

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