11 Midwest Weekend Getaways for Couples [2024]

The vibrant red Sturgeon Bay Canal North Pierhead Lighthouse in Door County, a maritime beacon for Midwest getaways, stands out against the blue sky and lake.

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 couples 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.

Whether it’s vibrant city life in Chicago with its iconic architecture along Lake Michigan, the rich heritage and brewery tours in Milwaukee, or the historical ambiance of Galena, couples are sure to find the perfect setting for romance and relaxation.

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. 

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.

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1. Chicago

Garfield Park Conservatory in 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 a $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 here.  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 prior to 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:

  • AIRE Ancient Spa or Peninsula Spa
  • Chicago Botanical Garden
  • Bike Lakeshore Drive

Stay: Hilton Chicago Magnificent Mile Suites

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 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:

  • Milwaukee Public Market
  • Historic Third Ward
  • Mitchell Park Domes

Stay: Cambria Hotel Milwaukee Downtown

Small Town

3. Holland

Windmill Island in 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:

  • Windmill Island
  • Nelis’ Dutch Village
  • Downtown Holland

Stay: Courtyard by Marriott Holland Downtown

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 time from the windy city brings couples to a laidback, 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:

  • Rivera Beach
  • The Riviera
  • Lake Geneva Shore Path

Stay: Harbor Shores or Bella Vista Suites

5. Door County

Sturgeon Bay by Salome Guruli via Unsplash

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 to reconnect and create lasting memories.

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:

  • Cave Point County Park
  • Trolley Tour
  • Door County Wine Trail

Stay: Country House Resort

6. Galena

Galena by Austin Goode via Unsplash

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.

The blend of adventurous activities and the opportunity to unwind makes Galena an ideal spot for those looking to create intimate moments and lasting memories together.

Best things to do:

  • Winery Tours
  • Skiing
  • Downtown Galena

Stay: Cloran Mansion Bed & Breakfast or Wyndham Garden Galena Hotel & Day Spa


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 of New Buffalo). 

But there is a 1 hours 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.  (Read about the best wineries in Michigan)

Best things to do:

  • New Buffalo Beach
  • Best Wineries
  • Downtown New Buffalo

Stay: Sunset Vista

8. Saugatuck

Oval Beach by Benjamin R. via Unsplash

Location: Michigan

Saugatuck, nestled along Michigan’s picturesque Lake Michigan shoreline, offers a distinctive blend of natural beauty, artistic flair, and adventurous activities.

The town’s crowning jewel, Oval Beach, is renowned for its golden sands and stunning sunsets, providing a romantic backdrop for evening strolls and relaxed afternoons beside the waves.

For those seeking a blend of adventure and scenic beauty, Saugatuck Dunes State Park presents sprawling sand dunes that offer hiking trails with breathtaking views.

Art enthusiasts will be delighted by the vibrant art scene, characterized by numerous galleries showcasing works from local and national artists, inviting couples to immerse themselves in the creative spirit of the town.

Additionally, boat rentals offer a unique opportunity to explore the waters together, whether it’s a leisurely paddle along the Kalamazoo River or a more adventurous outing on Lake Michigan.

Combining these elements, Saugatuck emerges as an ideal destination for couples looking to create lasting memories through shared experiences in nature, art, and adventure.

Best things to do:

  • Oval Beach
  • Saugatuck Dunes State Park
  • Downtown Saugatuck

Stay: Starlite Resort


9. Starved Rock

A slender waterfall trickles down a moss-covered rock face in the lush Starved Rock State Park in Illinois. The natural beauty of the scene, with its vibrant greenery and gentle water flow, offers a tranquil escape for those seeking a nature-filled spring break in the Midwest.

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 a rainfall most common in the spring. 

My personal favorite seasons to visit 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:

  • La Salle Canyon
  • French Canyon
  • Boat tour

Stay: Starved Rock Lodge or Rustic Villa

10. Matthiessen

Stepping stones lead to a wooden staircase beside a small waterfall at Matthiessen State Park. The lush greenery and serene water create a perfect hiking backdrop.

Location: Illinois

Matthiessen State Park is an exceptional Midwest retreat for couples seeking a mix of adventure and tranquility.

Its idyllic setting boasts miles of hiking trails that meander through lush forests, leading to stunning waterfalls and serene, verdant landscapes.

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 combining a visit 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:

  • Lake Falls or Cascade Falls
  • Dells Canyon
  • Giant’s Bathtub

Stay: Rustic Villa

11. Mackinac Island

Midwest road trip to a serene lakeside in Mackinac Island, Michigan. There is a white lighthouse overlooking the clear blue waters, flanked by vibrant greenery and a no trespassing white picket fence.
Mackinac Island by Vincent Yuan via Unsplash

Location: Michigan

Mackinac Island, nestled in Michigan, emerges as a quintessential Midwest destination for couples seeking a blend of adventure and sweetness. The island’s network of hiking trails meanders through lush landscapes, leading to the iconic Arch Rock, where couples can marvel at panoramic views of the shimmering lake below.

Renting bikes offers an intimate way to explore the island’s charming nooks, fostering moments of joy and discovery at every turn.

Additionally, the island is famous for its exquisite fudge, making the experience of sampling different flavors a delightful excursion in itself.

With its unique combination of natural beauty, recreational activities, and culinary treats, Mackinac Island stands out as a romantic retreat that promises lasting memories for every couple.

You can even extend your visit on a Midwest road trip through Michigan.

Best things to do:

  • Arch Rock
  • Fudge tasting
  • Bike rental

Stay: Grand Hotel


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!

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As a full time employee who loves her job, learn how I honor my wanderlust while working a 9:00-5:00 (because I want to!) This blog welcomes all, and specifically provides resources for those seeking travel intertwined into a busy schedule (3 days to 5 weeks).