Most Romantic Getaways From Chicago

The most romantic getaways from Chicago whether you enjoy nature, beaches or charming small towns.

Romantic Getaways From Chicago

Looking for the most romantic getaways from Chicago? There are many romantic places in the Midwest that you can easily visit from Chicago whether planning a special anniversary or birthday trip for your significant other or looking for a couples weekend getaway from Chicago.

Make sure to check out my essential road trip packing list to make sure you have all your road trip travel essentials before you go!

And if you decide to stick close to home, here are the most romantic things to do in Chicago.

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Galena, Illinois

Galena Illinois is one of the most romantic getaways from Chicago
Galena is one of the romantic destinations close to Chicago for a weekend getaway. Galena is a charming and historic small town. A large portion of the city is listed on the National Register of Historic Places and there are many historical sights to explore including the Ulysses S. Grant Home, the Elihu B. Washburne House, Dowling House and the Old Market House.

Some things to do in Galena including shopping downtown at the many boutiques and antique stores, eating at local restaurants and wine tasting at local vineyards or exploring the hiking trails dotted throughout the area. Galena is close to Apple River Canyon State Park, an Illinois state park, where you can go hiking, fishing and more.

Stay: Country Inn & Suites by Radisson

Getting There: 164 miles driving distance from Chicago (about a 3 hour drive)

Cheap Car Rentals

Lake Geneva, Wisconsin

view from lake cruise in Lake Geneva which is a great romantic getaway near Chicago IL

Lake Geneva is a popular year round resort city. Couples can get an up close view of the beautiful mansions built by wealthy Chicagoans during the Gilded Age by taking a lake cruise.

Active couples can also walk all or part of the 21 mile Geneva Lake Shore Path around the lake. There are places to stop for lunch around the way.

Visiting in the summer? Lounge on the beach or get out on the water (you can rent just about anything including speedboats, jetskis, kayaks, pontoons). In the winter, you ski, snowboard, ice skate, snowshoe or visit the instagrammable ice castles. Other fun outdoor activities in Lake Geneva include hiking, zip-lining and golfing.

One of the most romantic things to do in Lake Geneva is to see the area from above on a hot air balloon.

Distance: 83 miles from Chicago (about a 90 minute drive) so you can also visit on a day trip from Chicago

Stay: Grand Geneva Resort & Spa -amenities at this AAA Four-Diamond resort include a spa, several restaurants and bars, indoor and outdoor pools, a golf course and more.

Elkhart Lake, Wisconsin

Elkhart Lake is a less known romantic weekend getaway from Chicago

Elkhart Lake is a quaint town where visitors can really experience an authentic summer lake getaway. Take a dip in the crystal clear waters, experience the various watersports (paddleboarding, kayaking, jet skiing), go fishing or just lounge around on a pool float.

While the lake is a big draw, there is so much more to the area. From hiking the picturesque Kettles, The Ice Age Trail or along the shore of Lake Michigan, there is no shortage of beautiful hiking spots.

Motorsports lovers and thrill seekers will want to check out Road America Racetrack, North America’s longest natural road racing facility.

In the winter, couples can enjoy fun activities in the area including dog sledding, snowshoeing, skiing and carriage rides.

Distance: 150 miles from Chicago (about 2.5 hour drive)

Stay: The Osthoff Resort – a premier AAA Four Diamond resort located on 500 ft of recreational lakefront. Their luxury Aspira Spa offers an indoor and outdoor whirlpool, sauna, meditation room, spa café and a complete range of treatments including massages, facials and body treatments.

Door County, Wisconsin

Door County, located in the northeast corner of Wisconsin, is a hidden gem full of charming villages and towns, lighthouses, state parks, vineyards, and outdoor attractions and activities.

Sturgeon Bay is a convenient base for exploring the area. The city is a fisherman’s mecca, with some of the best bass fishing in the world. You can also tour a restored tug, visit the Door County Maritime Museum, learn the history of Door County, stroll down historic 3rd Avenue, or enjoy nature at Potawatomi State Park on the city’s edge.

Explore one or more of several little towns located along the east and northeast coastline of Door County which full of unique shops, galleries, restaurants and breweries.

Bring your car or bike on the 30 minute ferry to Washington island, located northeast of the tip of the Door Peninsula.

Distance: 244 miles driving distance to Sturgeon Bay

Stay: Sturgeon Bay, Egg Harbor, Fish Creek, Bailey’s Harbor or Sister Bay all have good options

Saugatuck, Michigan

Saugatuck is a small city on the shores of Lake Michigan. It is a perfect getaway for couples looking to enjoy it’s many art galleries, stroll along Oval Beach and immerse themselves in the town’s unique charm. 

Saugatuck is also a good base to visit the many wineries in Southwest Michigan and nearby beach towns.

Distance: 146 miles from Chicago (about 2.5 hours).

Shawnee National Forest

Nestled between the Mississippi and Ohio Rivers in southern Illinois, the Shawnee National Forest is full of natural beauty, making it ideal for outdoor recreation from hiking to climbing.

The stunning Shawnee National Forest landscape features woodlands. hills, lakes, creeks, rock formations, cliffs and  bluffs. You can also see wildlife such as bad eagles.

Shawnee National Forest is the best place to go hiking in Illinois with spectacular views. Trails include the long River to River Trail and the Rim Rock National Recreational Trail. The must see attraction is the Garden of the Gods wilderness area featuring ancient sandstone cliffs and formations. Climbers should not miss the Jackson Falls climb on 60 feet of sandstone cliffs and boulders that include numerous freestanding towers.

If you enjoy wine, The Shawnee Hills Wine Trail features 11 wineries located along a 35-mile scenic drive along highway 127 and highway 51 in the Shawnee National Forest.

Distance: 300 miles from Chicago

Stay: Riverview Mansion Hotel (a unique boutique style mansion)

Mackinac Island, Michigan

Mackinac Island is a beautiful island in Lake Huron located between Michigan’s Upper and Lower Peninsulas. The car free island is one of the most romantic places to visit in the Midwest and was chosen as the Best Island in the Continental U.S. by Travel + Leisure. It is a long drive from Chicago to catch a ferry to the island so it is best to visit on a long weekend or a week long vacation.

Cars are not allowed on the islands so couples can get around the island by foot, bikes or on a horse-drawn carriages. Active couples can explore Mackinac Island State Park, Michigan’s first state park known for its the limestone Arch Rock formation. Make sure to try some of the island’s world-famous fudge.

Distance: About 421 miles (about 7 hours driving distance) to the top of the Lower Peninsula where you can take a short ferry (about 20 minutes) to the island.

Stay: Grand Hotel – This historic hotel has been ranked one of Travel + Leisure’s Top 10 Resort Hotels in the Midwest and Conde Nast Traveler’s Top 10 Mid-Atlantic and Midwest Resorts in 2021. Amenities include The Jewel golf course, Sadie’s Ice Cream Parlor, swimming, tennis, lawn games, gardens, bicycling, carriage tours, shopping and complimentary children’s programs.

Frankenmuth, Michigan

Frankenmuth is a small picturesque city known as Michigan’s Little Bavaria. It is a great place to visit any season with events happening year round. You can find a 3 day itinerary here.

Couples that enjoy Christmas will love visiting Frankenmuth during the holiday season. Shop at the world’s largest Christmas store while enjoying the towns holiday lights. (See more great Christmas getaways from Chicago here.)

Distance: About 298 miles (about 4.5 hours driving distance) from Chicago

Stay: Bavarian Inn Lodge

What are your favorite romantic getaway from Chicago?


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