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Best road trips from Chicago

Best Road Trips From Chicago

You are here: Home / North America / USA / Chicago / Best Road Trips From Chicago

//  by Lisa 4 Comments

During all the years I lived in Chicago (ugh…I still don’t like that that is past tense!), it was hard to leave the city to see other areas of the Midwest when there was still so much to see in the city!

But I did eventually take some road trips from Chicago and you know what? There’s a lot to love about the Midwest! I’ve been pleasantly surprised by vibrant cities like Indianapolis and Milwaukee, which are both experiencing renaissances. But what about some other midwest getaways?

From Michigan to Wisconsin to Indiana, here are some of the best weekend trips from Chicago!

 

Table of Contents

Toggle
  • Holland, Michigan
  • Traverse City, Michigan
  • Charlevoix, Michigan
  • Harbor Springs, Michigan
  • Lake Geneva, Wisconsin
  • Madison, Wisconsin
  • Door County, Wisconsin
  • Elkhart Lake, Wisconsin

Holland, Michigan

2.5-hour drive from Chicago

Holland, MI

At just two and a half hours from the Loop, Holland is one of the easiest and best weekend trips from Chicago. From the award-winning downtown to the white sandy beaches, Holland is brimming with small-town charm and big-city amenities with a touch of the Netherlands. You can browse downtown boutiques and galleries, hit one of the best farmers markets in the state, dine along the waterfront and visit local distilleries and breweries, hike to the top of a sand dune or climb to the top of a Dutch windmill, and go sailing and catch the brilliant sunset over Lake Michigan. Plus, don’t miss all the nearby trails and views at nearby Holland State Park.

 

Where to Stay

City Flats Hotel – hip, eco-friendly, LEED Certified boutique hotel

 

Traverse City, Michigan

(the next three destinations could be combined in the same road trip)

5-hour drive from Chicago

Chantal winery
Chateau Chantal Winery

Traverse City’s small-town lakeshore charm and art deco architecture make it one of the best road trips from Chicago and a perfect gateway to Northern Michigan’s breathtaking sights. Stop in for a glass of beer or wine at one of the many famous wineries and brewpubs, like Mari Vineyards or Mackinaw Brewing Company. One of my favorite breweries was Hop Lot Brewing Company in Sutton’s Bay.

Hop Lot Brewing
Hop Lot Brewing

Dine at some of Michigan’s best restaurants. Take in art at galleries and museums, and enjoy beach strolls before heading into the wilderness.

sleeping bear dunes hike
Sleeping Bear Dunes

From Traverse City’s quaint streets, you can head north and explore the Leelanau Peninsula, or veer west to Sleeping Bear Dunes National Lakeshore, one of the country’s best stretches of shoreline, with incredible dunes and westerly views revealing some of the best sunsets east of the Mississippi. You’re also within a stone’s throw of the coastal M-22, one of the most scenic drives in America.

Where to Stay:

Tamarack Lodge – a resort-like hotel offering luxury waterfront accommodations

 

Charlevoix, Michigan

Charlevoix Michigan

5.5-hour drive from Chicago

Charlevoix is an artsy little beach town filled with galleries, boutiques, and local restaurants. You can walk the Charlevoix South Pier to the lighthouse at the end or bike down the 26-mile Little Traverse Wheelway rail-to-trail bike path. Hunt for Petoskey stones — fossilized coral rocks exclusive to Michigan — at Fisherman’s Island State Park. Take a day trip out to Beaver Island, the largest island in Lake Michigan with over 100 miles of hiking trails and pristine waters for kayaking. Check out the architectural “Mushroom Houses” of Charlevoix, which look like hobbit huts. Plus, thanks to the area’s low levels of light pollution and dark night skies, the stargazing is wondrous. Watch the stars, Northern Lights, Milky Way, and meteor showers.

Mushroom House
Mushroom House

Where to Stay

Inn at Bay Harbor, An Autograph Collection Hotel – a resort destination in itself

Hotel Earl – brand new, mid-century modern, lux boutique hotel

Airbnbs:

Lakefront Retreat

Peaceful Lakefront Retreat

 

➙ Need a place to stay? Use my airbnb link for up to $40 off your first stay!
➙ Need an easy way to get around? Sign up for Uber or Lyft and get up to $10 in ride credits!
➙ Take a local tour in Michigan with Get Your Guide, offering unique city tours all over the world.

 

Sunset on Lake michigan
Sunset on Lake Michigan

 

Harbor Springs, Michigan

tunnel of trees michigan6-hour drive from Chicago

Harbor Springs can also be a day trip from Traverse City or Charlevoix. Situated on a beautiful natural, deep harbor, this tiny, waterfront community has a wonderful downtown business district with shopping and dining overlooking the water. Four seasons of outdoor fun offer amazing opportunities for families.  View the beautiful fall colors and drive the famous Tunnel of Trees on M-119 north of town, which provides a stunning drive along bluffs overlooking Lake Michigan.

 

Lake Geneva, Wisconsin

Lake Geneva mansions

1.5-hour drive from Chicago

One of the easiest and best weekend trips from Chicago is a quick drive up to Lake Geneva. Lake Geneva has been an escape place for Chicagoans for more than a century.  You can enjoy the cute shops in the historic downtown or get out on a boat on one of the many boat tours of the lake itself. One of my favorite things to do is stroll the 26-mile Lake Geneva Shore Path, a walking path that circles the entire lake.  It cuts right through the pastoral backyards of some amazing mansions that dot the lake. For more, check out my full post on things to do in Lake Geneva, Wisconsin.

Where to Stay

The Ridge Hotel

Timber Ridge Lodge

 

Madison, Wisconsin

madison WI

2.5-hour drive from Chicago

Madison boasts an inviting downtown situated between two lakes and the beautiful campus of the University of Wisconsin. This quintessential Midwestern city also happens to be the state capitol.

There are water sports, tons of hiking and biking trails and heaps of green space (260 parks and beaches!).  Don’t miss the Madison Museum of Contemporary Art or the Dane County Farmers’ Market, the largest producer-only farmers market in the United States.

Where to Stay
The Edgewater – Top-rated hotel

Airbnb  – Modern Lakeside Home

 

 

Door County, Wisconsin

Lighthouse Door County
Lighthouse – Door County, Wisconsin

3.5-hour drive from Chicago

Famous for its family-friendly attractions and 300 miles of gorgeous shoreline, Door County sits on a 75-mile-long peninsula sticking out into Lake Michigan. The Door Peninsula has more miles of shoreline, more state parks and more lighthouses than any other county in the United States. The area is full of wooded and winding country roads, quaint apple-picking farms, and sandy shores. It’s gorgeous in any season, but spring and autumn are pretty magical. Think Cape Cod or New England.

Just some things to do: boating, hiking, boutique shopping, lighthouses, and apple orchards. Eat at a fun, traditional Scandinavian outdoor fish boil and get ice cream at an old-timey ice cream parlor.

 

Where to Stay

Eagle Harbor Inn

White Gull Inn

 

Airbnb

Lakeside Cottage

 

 

Elkhart Lake, Wisconsin

2.5-hour drive from Chicago

Elkhart Lake is a resort village that focuses on wellness, whether at the Aspira Spa, the healing waters of spring-fed Elkhart Lake, or the organic gardens of The Osthoff Resort. But if wellness isn’t your top priority, don’t worry — the town also offers history, motor sports, boating and other lake activities ((kayaking, paddle boarding, boating), hundreds of miles of trails for biking, hiking and running at nearby Kettle Moraine State Forest, golfing, shopping, cooking classes, wine tastings, and unique bars and restaurants to keep the whole family satisfied.

 

Where to Stay
The Ostoff Resort – highly rated, all-inclusive, lakeside resort and spa

 

Airbnbs

The Pavilion

Farmhouse

 

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About Lisa

Lisa Lubin is an established travel/food writer and photographer, three-time Emmy® award-winning TV producer, video consultant, and travel industry expert. After more than a decade in broadcast television she took a sabbatical, which turned into three years traveling around the world. She created this blog in 2006. Lisa also owns LLmedia, a media & video consulting business. Her writing and photography has been published by American Way, Hemispheres, Wall Street Journal, Chicago Tribune, West Jet Magazine, Scandinavian Traveler, Orbitz, and Luxury Las Vegas. Her book, The Ultimate Travel Tips: Essential Advice for Your Adventures, is available on Amazon.

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Reader Interactions

Comments

  1. Mike Shubic (@MikesRoadTrip)

    January 18, 2022 at 2:07 pm

    Love Traverse City. I would have also included Beloit and Galena.

    Reply
  2. Babu Kaji Sitaula

    June 23, 2022 at 4:26 am

    Appreciate this wonderful post that you have provided for us. Great site and a great topic as well i really get amazed to read this.

    Reply
  3. Mani

    April 20, 2023 at 12:14 am

    Wonderful article..! thanks for sharing a useful guide .

    Reply
  4. shivani

    July 5, 2024 at 1:56 am

    “Your selection of the best road trips from Chicago is fantastic and inspiring! The images beautifully showcase the scenic routes and diverse destinations, making it a must-read for adventure seekers. Thanks for highlighting these exciting travel options!”

    Reply

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Lisa LubinI chucked it all – the TV job, the guy, the “normal” life – to travel around the world. I've been to 60+ countries & live a life based more on experiences. I want to inspire you to travel slowly & eat locally! MORE...

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