The Summer Chicago Road Trip Loop

When flying into Chicago, here’s a multi-day road trip that’s fun for the whole family that packs in some of the best spots in the Midwest:

Chicago, Illinois

As the largest city in the Midwest, Chicago is home to a vibrant and diverse tourism scene, drawing millions of visitors annually. Chicago offers a New York City feel paired with a friendly Midwestern attitude. From sprawling city parks to a bustling city center and the dining and entertainment to match, Chicago is a must-stop on any Midwest road trip. Catching a Cubs game at the historic Wrigley Field, discovering the wonders of the world at the Field Museum, or simply relaxing on the beach on the shores of Lake Michigan are just a few of the many adventures road trippers can find while exploring Chicago.

Door County, Wisconsin

Door County is the easternmost county in Wisconsin, named after the strait between the Door Peninsula and Washington Island. Nicknamed the “Cape Cod of the Midwest”, Door County is a popular vacation destination that offers 300 miles of Lake Michigan shoreline, five state parks, 19 county parks and thousands of acres of wilderness. From boutique bed & breakfasts and award-winning restaurants to wineries, lighthouses and family-friendly entertainment, Door County is a destination that truly offers something for everyone.

Duluth, Minnesota

Duluth is a port city situated on Lake Superior in northern Minnesota, offering a perfect blend of city and nature. The city is home to a variety of great restaurants, shopping, entertainment and sights including the Great Lakes Aquarium, the Aerial Lift Bridge, next to Canal Park and Minnesota Point, known locally as Park Point. The Point is the world's longest freshwater bay-mouth sandbar, offering six miles of Lake Superior beachfront. Duluth also serves as the gateway to the famous North Shore drive along Lake Superior, which runs all the way to the Canadian border.

Mackinaw City & Mackinac Island, Michigan

Mackinaw City is a village on the northern tip of Michigan’s lower peninsula and serves as the gateway to the famous Mackinac Island. Mackinaw City is a picturesque destination offering a unique blend of history, nature and modern attractions. From Mackinaw City, take a moment to enjoy a slower, simpler speed of life by hopping the ferry to Mackinac Island, a small car-free island within Lake Huron. The island offers scenic views to be enjoyed via bicycle or horse-drawn carriage, a quaint downtown lined with shops, art galleries and famous handmade fudge makers, as well as a historic British Revolutionary War fort based on a former fur trading post. With all they entail, Mackinaw City and Mackinac Island promise an unforgettable vacation experience for visitors of all ages.

Dubuque, Iowa

As Iowa’s oldest city, Dubuque offers the quietness of a medium-sized Midwest city paired with scenic views of the Mississippi River and a rich history. Visitors can discover the history and nature of the region at the National Mississippi River Museum and Aquarium or take in the city’s largest and widest view after a ride on the Fenelon Elevator, the world’s shortest, steepest railway. Adults can try their luck at two different casinos in the area. Dubuque offers history from around the world in every corner as the place “Where Iowa started.”

Whether traveling through one of the destinations listed above or creating a route to visit a handful of new locations, a road trip around the Midwest is the perfect way to soak in the ultimate summertime weather, learn some unique history, take in beautiful scenery and create memories that will last a lifetime.