Are you looking for a Midwest weekend getaway for couples? This guide features 11 locations with practical reasons about why they are the best spots for a couple’s getaway!
As a Midwest local, I can tell you firsthand that there is tons to experience in this less-explored region of the US.
Small towns, bustling cities, and serene nature retreats provide just about everything you need for a couples’ weekend getaway.
The Midwest, often celebrated for its charming small towns, scenic landscapes, and friendly locals, makes an ideal destination for couples seeking a weekend getaway.
Away from the hustle and bustle of the coasts, the region offers a unique blend of cultural experiences, outdoor activities, and culinary delights, all within the comfort of easy drives and welcoming communities.
These off-the-beaten-path, lesser-known experiences allow you to craft a weekend of relaxation or adventure with your significant other and make it all your own.
11 of the best Midwest weekend getaways for couples include Chicago, Milwaukee, Holland, Lake Geneva, Door County, Galena, New Buffalo, Saugatuck, Starved Rock, Mathiessen, and Mackinac Island.
11 Midwest Weekend Getaways for Couples
City
1. Chicago
Location: Illinois
Chicago provides a bustling city getaway in the Midwest for couples. There are tons of classic Chicago tourist attractions for couples to experience in the windy city together, like Millenium Park or towering skyscrapers.
But Chicago attractions extend far beyond the tourist route. Couples looking for relaxation may consider AIRE Ancient Baths Spa in West Town or Peninsula Spa in the Gold Coast neighborhood.
Peninsula has a huge price tag but always ranks at the top of any “best spas” list. For example, the cheapest spa service as of March 2024 is an $80 manicure.
AIRE is my top-priority spa to make it to right now. The Roman, Ottoman, and Greek thermal bath experience is intriguing and the only one like it in the area.
Another of my favorite couples activities in Chicago is a flower walk any time of year.
Chicago Botanic Garden is the most popular location, but it’s about 20 minutes outside of Chicago, so you will need public transportation or a rideshare service to get there. Entrance costs vary, so I recommend checking the website before your trip.
Free alternatives include Lincoln Park or Garfield Park conservatories. These beautiful glass greenhouses are entirely free. You just need to make a timed entry reservation on both conservatory websites before arrival.
There have been safety concerns in the Garfield Park neighborhood, something to take into consideration. My visit to the Garfield Park Conservatory felt very safe, and it was beautiful.
Best things to do in Chicago:
- AIRE Ancient Spa or Peninsula Spa
- Chicago Botanical Garden
- Bike Lakeshore Drive
⭐Stay: Hilton Chicago Magnificent Mile Suites
Popular Chicago Tours
2. Milwaukee
Location: Wisconsin
Milwaukee is a fun, quirky city, perfect for a weekend of exploring with your significant other. I recommend Milwaukee for couples who like new city experiences, eclectic vibes, and exploration.
My favorite thing to do in Milwaukee is to dine at the Milwaukee Public Market. Couples can stroll through vibrant market stalls, sampling local food options followed by a walk on the Milwaukee Riverfront.
Feeling adventurous? They have some newly renovated Pickleball courts right across from the Public Market… and the court has a ROOF! Pickleball rain or shine? Thanks, Milwaukee.
Some of the other best activities in Milwaukee on a weekend away include exploring museums like Milwaukee Public Art or Harley-Davidson, shopping in the Historic Third Ward, and taking brewery tours.
This unique city also features some top-name performances. In 2023, the Fiserv Forum featured celebrities like Adam Sandler and Bruce Springsteen.
Tip: Catch a show at the nationally acclaimed outdoor music Festival, Summerfest, if you visit in the summer.
Best things to do in Milwaukee:
- Milwaukee Public Market
- Historic Third Ward
- Mitchell Park Domes
⭐Stay: Cambria Hotel Milwaukee Downtown
⭐Highly Rated Milwaukee Tours
Small Town
3. Holland
Location: Michigan
Holland is an adorable, Dutch down located in Southern Michigan. Its European ambiance, small-town charm, and prime location near several Lake Michigan beaches make it an ideal couples getaway.
Visitors can step into a slice of the Netherlands at Nelis’ Dutch Village, where traditional Dutch architecture and tulip gardens provide a charming cultural experience.
A visit to Windmill Island not only presents an opportunity to see a working Dutch windmill but also to enjoy tranquil gardens and historical exhibits.
Downtown Holland enhances the experience with its vibrant shopping scene, where quaint boutiques and local artisans sell unique goods.
The dining scene is equally impressive, offering cozy cafes and upscale restaurants perfect for romantic dinners.
Together, these attractions make Holland, Michigan, a captivating destination for couples seeking both adventure and relaxation.
The best time to visit is spring for the annual Tulip Time Festival. This is one of my favorite activities in Michigan!
Best things to do in Holland:
- Windmill Island
- Nelis’ Dutch Village
- Downtown Holland
4. Lake Geneva
Location: Wisconsin
Lake Geneva is one of the most popular weekend trips or day trips from Chicago. Its 1.5-hour drive from the windy city brings couples to a laid-back lake town with tons of activities every season of the year.
The town’s quaint streets are lined with unique shops, offering the perfect setting for a leisurely stroll and a bit of shopping.
When the sun sets, Lake Geneva’s nightlife comes alive with intimate bars and live music venues, ensuring the end of the day is as exciting as the start.
Feeling adventurous? Hike or bike the 21-mile Lake Geneva Shore Path, or take to the sky on a zipline adventure or hot air balloon ride.
Best things to do in Lake Geneva:
- Rivera Beach
- The Riviera
- Lake Geneva Shore Path
⭐Stay: Harbor Shores or Bella Vista Suites
5. Door County
Location: Wisconsin
Door County, just a 2.5-hour drive from Milwaukee, WI, emerges as an idyllic Midwest getaway.
This picturesque peninsula, surrounded by the sparkling waters of Lake Michigan and Green Bay, enchants visitors with its panoramic views.
Seasonal activities like cherry picking in summer, scenic autumn drives, and winter snowshoeing along silent, snow-covered trails provide variety for each couple.
The region’s lighthouses and sunset spots offer romantic backdrops for memorable moments.
Whether it’s savoring the local cuisine at cozy restaurants, exploring art galleries, or simply basking in the serene beauty of the outdoors, Door County stands out as a perfect retreat for couples.
The best time to visit is in the fall, not only for the spectacular Midwest fall foliage but also for the delightful harvest festivals and the comfortable, crisp weather perfect for outdoor exploration.
Best things to do in Holland:
- Cave Point County Park
- Trolley Tour
- Door County Wine Trail
⭐Stay: Country House Resort
⭐Popular Door County Tours
6. Galena
Location: Illinois
Located in the rolling hills of Western Illinois is the charming small town of Galena! Famous for its wineries and small-town vibes, it makes for a perfect vacation destination any time of year.
In the winter, the Chestnut Mountain Ski Resort turns the town into a snowy paradise, offering exhilarating ski slopes and breathtaking views of the Mississippi River.
Year-round, couples can tour the local vineyards, tasting exquisite wines while surrounded by serene vistas.
Best things to do in Galena:
- Winery Tours
- Skiing
- Downtown Galena
⭐Stay: Cloran Mansion Bed & Breakfast or Wyndham Garden Galena Hotel & Day Spa
Beach
7. New Buffalo
Location: Michigan
New Buffalo is a quaint Midwest getaway for couples. Its small-town ambiance with miles of shoreline along Lake Michigan makes it great for couples looking to relax.
Downtown New Buffalo features cozy restaurants for all budgets.
I love the ambiance of Brewster’s New Buffalo. It makes for a perfect romantic evening. I recommend sitting on the patio outside if the weather is warm. The exterior decor makes you feel like you have stepped into Italy!
The most famous restaurant is Stray Dog. This famous rooftop restaurant is a staple of the small town. Couples can enjoy brunch, dinner, or nightlife experiences here!
Want to get out on the water? Several tour operators offer boat rentals and sunset cruise tours from Union Pier, Michigan (only 15 minutes outside New Buffalo).
But there is a 1-hour time zone difference, so be mindful of this while planning.
My sunset cruise experience was pretty crowded, and you need to arrive early if you want a seat on the top deck of the boat.
Ready to relax? The golden sands of Buffalo Beach is a great place for couples to bike to.
Parking at the beach costs around $15. Check the website for the most up-to-date entrance costs or swimming conditions.
New Buffalo’s charm extends beyond its scenic beaches to some of the best wineries in the region, where couples can savor local wines amidst the picturesque landscapes of Michigan.
Some of the best wineries include Hickory Creek, Dablon Vineyards, and more.
Best things to do in New Buffalo:
- New Buffalo Beach
- Best Wineries
- Downtown New Buffalo
⭐Stay: Sunset Vista
8. Saugatuck
Location: Michigan
Saugatuck is another lovely small town along Michigan’s picturesque Lake Michigan shoreline.
One of the best activities is winding down at Oval Beach. It’s known for golden sands and stunning sunsets, providing a romantic backdrop for evening strolls and relaxed afternoons beside the waves.
Add a bit of hiking adventure to your couples getaway at Saugatuck Dunes State Park!
There is also plenty to do in Downtown Saugatuck. There are many galleries, small restaurants, and local bars.
You can also rent a boat on the Kalamazoo River or Lake Michigan!
Best things to do in Saugatuck:
- Oval Beach
- Saugatuck Dunes State Park
- Downtown Saugatuck
⭐Stay: Starlite Resort
Adventure
9. Starved Rock
Location: Illinois
Starved Rock is an off-the-beaten-path adventure experience for couples!
Spend the weekend chasing waterfalls, hiking, and exploring the incredible sandstone canyons at Starved Rock State Park in Utica, Illinois.
Couples can plan for flowing waterfalls after rainfall. This is most common in the spring.
My personal favorite seasons to visit Starved Rock are winter for the possibility of frozen waterfalls (something out of a movie, seriously) or fall for the rainbow foliage.
The Starve Rock Lodge is the only hotel located in the state park itself. Couples have their pick of staying in a cozy cabin or inside the hotel itself.
Featuring a pool and restaurant on site, it provides the balance of couples’ relaxation after a day of adventure and hiking.
Other top activities for couples in Starved Rock include boat rentals or tours, trolley rides, or exploring the small town of Utica.
It’s also a top Midwest spring break destination.
Best things to do in Starved Rock:
- La Salle Canyon
- French Canyon
- Boat tour
⭐Stay: Rustic Villa
10. Matthiessen
Location: Illinois
Matthiessen State Park is an exceptional Midwest retreat for couples seeking a mix of adventure and tranquility.
Matthiessen is known for its beautiful hiking trails through lush forests leading to stunning waterfalls.
The park offers an intimate atmosphere for couples to explore the natural beauty together, finding secluded spots for picnics or quiet reflection.
Whether it’s the thrill of discovering hidden waterfalls or the peacefulness of the surrounding nature, Matthiessen State Park provides the perfect backdrop for a romantic weekend getaway.
Tip: Consider a combined trip to both Matthiessen and Starved Rock state parks! They are located only 10 minutes apart, and they are both free.
Matthiessen also features some of the best hiking in the Midwest.
Best things to do at Matthiessen State Park:
- Lake Falls or Cascade Falls
- Dells Canyon
- Giant’s Bathtub
⭐Stay: Rustic Villa
11. Mackinac Island
Location: Michigan
Mackinac Island is a top Midwest couples getaway!
The island’s network of hiking trails leads to the iconic Arch Rock, where couples can marvel at panoramic views of the shimmering lake below.
Couples can spend a low-key afternoon exploring the small island by renting bikes.
Additionally, the island is famous for its exquisite fudge, so get ready to taste some free samples!
With its unique combination of natural beauty, recreational activities, and culinary treats, Mackinac Island stands out as a romantic Midwest retreat.
You can even extend your visit on a Midwest road trip through Michigan.
Best things to do on Mackinac Island:
- Arch Rock
- Fudge tasting
- Bike rental
Stay: Grand Hotel
Conclusion
The Midwest offers tons of destinations for couples taking a vacation.
If you are looking for adventure, the towering canyons and seasonal waterfalls of Starved Rock and Matthiessen State Park in Illinois will be your pick.
Itching for city life? Chicago balances urban attractions with serene retreats like spas and flower gardens.
Whether it’s a cozy stay in a lodge, a bike ride through scenic trails, or a leisurely day spent tasting fudge, the Midwest is filled with opportunities to make unforgettable memories together!
