Romantic Getaways for Chicago Couples

Romantic Getaways for Chicago Couples

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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.

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.

Milwaukee, Wisconsin

romantic getaways near chicago photo credit pabst mansion
Photo credit: Pabst Mansion/Visit Milwaukee

  • Drive from Chicago: 1 hour and 30 minutes

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

romantic getaways near chicago french lick photo credit visit 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.

Lake Geneva, Wisconsin

romantic getaways near chicago lake geneva photo credit the ridge
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 hike at Kishwaketoe Nature Conservancy. Set your hearts aflutter on a zipline with Lake Geneva Adventures. 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.

Elkhart Lake, Wisconsin

romantic getaways near chicago osthoff resort
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.

Galena, Illinois

blaum brothers distillery photo credit illinois office of tourism
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 nice stroll peaking inside shop windows. Snuggle up at Eagle Ridge Resort and Spa.

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

romantic getaways st joseph michigan photo credit amber kiel
Photo credit: Amber Kiel

  • Drive from Chicago: 1 hours and 35 minutes

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

the american club photo credit kohler co
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.

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.

Indiana Dunes, Indiana 

IOTD Dunes CreditLakeshoreCVA EricHines IndianaDunesSunrise medium
Photo credit: Visit Indiana

  • Drive from Chicago: 51 minutes

Take a walk in the sand at West Beach or a dip in Lake Michigan with your loved one. If you’re in the mood for some great views, take a stroll along the lakefront at Indiana Dunes National Park. Grab a bite to eat at the Pavilion and enjoy a seat right on the water.

Check into the Songbird Prairie Inn and Spa for a nice, relaxing time. They have a whirlpool bath and a fireplace to keep warm in the cooler months. This bed and breakfast was named one of the best romantic inns in the Midwest along with other accolades throughout the years.

Door County, Wisconsin

midwest family vacations door county cave point county state park cliff credit cheryl eugenio
Photo credit: Cheryl Eugenio

  • Drive from Chicago: 4 hours

This romantic spot is on a peninsula between Lake Michigan and Green Bay. It’s known for its shoreline and many parks, including Potawatomi State Park, Peninsula State Park, Rock Island State Park, Whitefish Dunes State Park, Newport State Park, Cave Point County Park and many more. 

Stay at The Ashbrooke Hotel, which is just a short walk from Egg Harbor Beach Park. This hotel is an adults-only hotel and perfect for a romantic getaway. Couples can also enjoy wine tasting or going on a wine tour at Door Peninsula Winery.

Indianapolis, Indiana

iStock Indianapolis 000044794280 XXXLarge medium
Photo credit: Visit Indiana

  • Drive from Chicago: 3 hours

Book a gondola ride and imagine you’re in Venice, Italy while you glide down the city’s Central Canal. Check out the “LOVE” sculpture located at the Indianapolis Museum of Art at Newfields. Take photos in The Garden, which features more than a half a million blooms.

The JW Marriott offers couples a romantic package, which features a $25 food and beverage voucher, late checkout and macaron assortments and champagne upon arrival. Check out the music scene at The Jazz Kitchen or indulge in some sweets at Gallery Pastry Shop.

St. Louis, Missouri

Gateway Arch National Park
Photo credit: Visit Wisconsin

  • Drive from Chicago: 5 hours

There are plenty of romantic activities to do in St. Louis.  Stay in The Fleur-De-Lys Mansion, an exclusive bed and breakfast once a 19th-century mansion. Some local attractions to check out are Missouri Botanical Garden, Grand Center Arts District, Tower Grove Park and Jazz at the Bistro.

There is plenty to do at St. Louis Station, including mini golf, ropes course, mirror maze, aquarium and the wheel. You must go up on The St. Louis Wheel and see the St. Louis skyline while you’re here. Of course, your trip won’t be complete without seeing the St. Louis arch and getting some amazing pics of it!

Traverse City, Michigan

fall getaways traverse city photo credit traverse city tourism
Photo Credit: Traverse City Tourism

  • Drive from Chicago: 5 hours

Take in the scenery and views of Lake Michigan at Sleeping Bear Dunes. Beaches you should check out near here are Peterson Beach Sleeping Bear Recreation, Sleeping Bear Dunes National Lakeshore, Empire Beach, Glen Lake Beach Park, Sleeping Bear Dunes Beach, North Bar Lake and many more.

One of the best things in Traverse City is the winery scene. There are more than 20 different wineries you can try out with your significant other along the coast. There are plenty of hotels, resorts, cabins, cottages, bed and breakfast and campgrounds for you to choose for your stay.

Lake Geneva, Wisconsin

Lake Geneva Cruise Line. Photo credit: Walworth County Visitors Bureau

  • Drive from Chicago: 1.5 hours

Couples will enjoy a romantic stay at the AAA Four Diamond-rated Grand Geneva Resort and Spa. This resort is set overlooking a private lake and has many amenities to try out like swimming pools, tennis courts, snow-sport facilities, golf courses, restaurants and a spa.

Get a drink at Barrique Bistro & Wine Bar, Geneva Tap House, Topsy Turvy Brewery or Studio Winery + Geneva Lake Distilling or go sightseeing on the Lake Geneva Cruise Line.


romantic getaways near chicago fairmont chicago jared powell photography fairmont
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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