5 Places to Go by Car from Chicago

Dr. Jessie Voigts's picture

Chicago is such a gorgeous city, packed with arts, culture, sports, and, of course, located right on Lake Michigan. But perhaps you’d like to explore more of the Midwest? You’ve come to the right place! Rent a car from the Chicago Airport (either O'Hare or Midway) and discover these 5 fabulous places, all within driving distance, and making a road trip loop around Lake Michigan, and a bit further west. 

5 Places to Go by Car from Chicago

Drive East to Michigan’s Sunset Coast

First, drive easily along 94, up to Michigan’s sunset coast. Here, you’ll find plenty of beach towns that are the perfect mix of good food, the arts, clean sand, and, of course, Lake Michigan unsalted. We have our favorite beaches, but you will certainly find your own! 

Heading north, I recommend stopping in South Haven and swimming on North Beach (less crowded), and then heading back across the river to dine at Clementine’s (try the onion rings!) before catching the sunset from South Beach, with the pier and lighthouse reflecting in the water. If you have a bit more time, head to the Michigan Maritime Museum, and take a sunset cruise on an historic tall ship.

Keep driving! A few hours north (and many beach towns and ice cream shops in between) is Manistee. This town turns 150 this year, and is celebrating! We love to watch the 4th of July fireworks from the beach.

Further north is Sleeping Bear Dunes National Lakeshore (named the most beautiful place in the US!) and Traverse City, a wine and foodie town that loves all seasons equally. 

South Haven's South Beach lighthouse and pier. From 5 Places to Go by Car from Chicago
South Haven's South Beach lighthouse and pier

Keep Heading North!

From Traverse City, drive further along Lake Michigan, stopping at the Headlands International Dark Sky Park, located in Mackinaw City. After you wonder at those gorgeous skies, the next day, take a ferry to Mackinac Island (pronounced Mackinaw!), and rent a bike to circle the island, and reward yourself with famous Mackinac Island fudge. Back on land, delve into history at Fort Michilimackinac, an 18th century French (and later British) fort and trading post. It's now a National Historic Landmark, part of Colonial Michilimackinac State Park in Mackinaw City, and open air historical museum. 

Cross the bridge (affectionately called the Mighty Mac) to the Upper Peninsula, and keep going along your Lake Michigan road trip. Stop for smoked fish and freshly made pasties, as you drive along the shore toward Wisconsin. 

The Mighty Mac. From 5 Places to Go by Car from Chicago
The Mighty Mac

Go Packers!

Drive over to Green Bay, Wisconsin, home of the Green Bay Packers football team. Besides sports, and, of course, local wineries and breweries, there's an active arts scene. The Green Bay Film Festival is held in March, and in August, the annual Artstreet Festival is worth a visit. Several theatres and art galleries will enhance your time spent in town. Note: Cheeseheads are not appropriate theatre attire, even here, in a town known for their love of football.

Nearby, Door County is the Midwest’s version of Bar Harbor, Maine–but it’s on an extremely driveable peninsula. Be sure to take a winery tour, golf, ride horses, take a ferry to Washington Island and Rock Island, and walk the scenic downtown Egg Harbor. Perhaps our most important recommendation is to dine at a fish boil–it’s not only a delicious meal, but also a full evening of entertainment. Catch the sunset from Eagle Bluff Lighthouse.

Eagle Bluff Lighthouse. From 5 Places to Go by Car from Chicago
Eagle Bluff Lighthouse

The Twin Cities

Oh, the Cities. What DO I say? You could spend your whole life here and not see and do all that you wanted to. But let’s say you only have a few days in town (alas!). Here’s what to do:

Pay homage to Prince at First Avenue downtown (catch a show or take photos of the stars painted on the exterior), and Paisley Park, his home and recording studio. I cannot stress enough the importance of this extraordinary musician on the local (and global) music scene. Utilize your car radio on the drive over, and listen to The Current’s Purple Current stream, to listen to Prince and explore his musical legacy. Prince loved basketball (it’s often been called his first love)–head to a Minnesota Timberwolves NBA or Minnesota Lynx WNBA game in downtown Minneapolis.

Shop at the Mall of America, an enormous mall, complete with indoor aquarium and theme park. You can eat well in the Cities, with a plethora of global cuisines, coffee shops, and local eats. Perhaps you’ve heard of the Jucy Lucy (I know, it’s spelled differently) burger, packed with molten cheese. There’s a rivalry in town as to the BEST Jucy Lucy…I dare you to try them all and discover your own favorite. Let me know!

The arts are alive and well, as is theatre (we absolutely love the Guthrie Theatre, and highly recommend seeing at least one show while you’re in town). Head to the University of Minnesota Twin Cities campus (one of my alma maters) and visit the Weisman Art Museum, designed by Gehry. Locals affectionately call it the exploding tuna can. The Minneapolis Institute of Art is worth many hours of your time, with its world-class collections. Best of all, general admission is free! Wander the Walker Art Centery & Minneapolis Sculpture Garden and pose for a photo with the iconic Spoonbridge and Cherry. 

Spoonbridge and Cherry. From 5 Places to Go by Car from Chicago
Spoonbridge and Cherry

Dine Well in Milwaukee

When driving back to Chicago’s O'Hare Airport, save time on your road trip to visit Milwaukee. It is a vibrant city, packed with sports, theatre, arts, culture, beaches, coffee, and food. 

There's a great variety of ethnic eats in town (here are our 12 favorites), as well as delicious coffee (Anodyne!), frozen custard (Leons!), and, of course, cheese curds.

There's more to Milwaukee than food, though (I know, right?!). The Milwaukee Museum of Art is located right on Lake Michigan, and has an enormous sunscreen that moves twice daily. It's incredible! If you're interested in historic buildings, as well as beer, tour the Pabst Mansion...and the old Pabst brewery! Wander the Harley-Davidson Museum, located on 20 acres along the river. At night, take a ghost tour…boo!

Milwaukee Museum of Art. From 5 Places to Go by Car from Chicago
Milwaukee Museum of Art

Road Trip Car Rental Details:

The Midwest is big! When you rent your car, ascertain your luggage needs, desired comfort level, budget, and how many people are lucky enough to road trip with you. Most car rentals have several types of car classes available, including economy, standard, intermediate, minvan and premium. The rates will differ according to the type of car class you choose, of course. 

Gas is generally pay at the pump via card, and do it yourself.

The highway speed limit is usually 70mph; smaller highways are 55mph. In town, plan to drive around 30-35, depending on posted speed. 

The Midwest is REALLY good at providing rest areas for road trippers! Road signs will indicate the next rest area. You’ll find clean bathrooms, water fountains, road maps, sometimes vending machines, always picnic tables, and even dog runs.

Tip: Look carefully at the number of passengers, luggage, and car amenities before you rent!  

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5 Places to Go by Car from Chicago