Illinois and Wisconsin may share a border, but you’ll find lots of different experiences between the two states in the heart of America’s Midwest. Pack your bags: on this five-day adventure, you’ll start at the famous shops of Chicago before traveling to a charming Mississippi River town in western Illinois. From there, you’ll explore Wisconsin’s beautiful capital city before heading to Milwaukee, home of Harley-Davidson and Miller Brewing Company.
Day 1: Chicago shopping and the blues
When you arrive in Chicago, you may want to park your car–public transportation is plentiful and the downtown is very walkable. Along Chicago’s famous Michigan Avenue, you’ll find the Magnificent Mile, a collection of outstanding shopping centers and retailers, all located on the same short walk. Whether you’re looking for a chic boutique, a specialty retailer or an iconic department store, you’ll find it all along Michigan Avenue. Plus, the area hosts a Magnificent Mile Shopping Festival at the end of every summer.
In the evening, consider attending a great blues show at Buddy Guy’s Legends. Located near Grant Park in Chicago, Buddy Guy’s Legends is a classic blues club that features live music seven nights a week, from up-and-coming artists to well-known performers. If you’re hungry, grab a bite to eat from their New Orleans-inspired menu.
Other options: Get up close and personal with sea life of all sorts at Shedd Aquarium, the largest indoor aquarium in the world, which features more than 8,000 aquatic animals. Visit the landmark Navy Pier, a Chicago icon that celebrated its 100th anniversary in 2016.
Day 2: Chicago: The art of the Windy City
Two icons along the Chicago lakefront, Millennium Park and the Art Institute of Chicago are two-must see attractions when traveling to the Windy City. Stop by and take a selfie at Cloud Gate (aka “The Bean”) or explore the Lurie Garden. At the Art Institute, explore more than 300,000 works of art, including famous works like Edward Hopper’s “Nighthawks” or Grant Wood’s “American Gothic.”
If you want to rest your feet while still getting a chance to explore Chicago, take advantage of one of the many boat tours available to visitors. These tours cover the Second City’s fascinating history, architecture and more.
Chicago is known the world over for its deep-dish pizza, and there are plenty of places to find this tasty treat. While there’s some debate over where to find the best deep-dish pizza in the city, a few places to try are Lou Malnati’s, which has been serving customers since 1971; Giordano’s, which has more than 40 restaurants in the Chicago area; and Gino’s East, one of the longest-running deep-dish pizzerias in Chicago.
Other options: Get a birds-eye view of the city at Willis Tower, and if you’re really daring, visit Skydeck Chicago, where you can stand on a glass balcony that extends four feet outside the 103rd floor of the building. Check to see if either of Chicago’s Major League Baseball teams—the Cubs in the National League and the White Sox in the American League—are in town during your visit.
Day 3: Digging up adventure in Galena
Located a few hours west of Chicago along the Great River Road, the small historic mining town of Galena, Illinois, has been named one of the top destinations in the Midwest and offers a combination of historical charm and beautiful scenery. Main Street is filled with antique stores, gift stores, and quaint snack shops and restaurants, and visitors can also explore the home of U.S. President Ulysses S. Grant.
Galena’s rolling hills in the Mississippi River Valley are home to several award-winning, scenic wineries. Visit Galena Cellars Vineyard & Winery or Massbach Ridge Winery & Tasting Room or plan your visit during one of Illinois’ numerous wine festivals and events.
Other options: If you’re interested in drinks other than wine, pay a visit to the Blaum Bros. Distilling Company, a family-owned and operated craft distillery that makes whiskey, vodka, gin and other spirits. If you’re in the area in June, don’t miss the Great Galena Balloon Race, a popular hot-air balloon event.
Day 4: Capitol adventures in Madison
Less than two hours from Galena, you’ll find the college town of Madison, Wisconsin. Downtown Madison is home to State Street, a pedestrian mall that runs from the campus of the University of Wisconsin-Madison to the Wisconsin state Capitol at the other end. Along the way, you’ll find restaurants, specialty shops and more. Take a tour of the Capitol, which was constructed in the 1850s. And you’ll find more shops and restaurants surrounding the Capitol building on Capitol Square.
Williamson Street (or “Willy Street”) on Madison’s East Side is an eclectic neighborhood filled with unique restaurants and charming shops. Stop by the Willy Street Co-op, a full-service natural-foods store, to pick up fresh produce and organic food, or take your taste buds on a world tour at neighborhood restaurants that feature everything from Asian to African to American cuisine.
Other options: Tour the Monona Terrace, a Frank Lloyd Wright-inspired building that sits on the shores of one of the four lakes in the Madison area. Take some time to explore the beautiful campus of the University of Wisconsin-Madison, including the historic Memorial Union, another lakeside attraction.
Day 5: Beer and motorcycles in Milwaukee
About 90 minutes from Madison on the Lake Michigan short, you’ll find Wisconsin’s largest city. The Milwaukee Art Museum gives the city’s waterfront its iconic look, thanks to an addition designed by famed architect Santiago Calatrava. The museum—one of the largest art museums in the country—boasts more than 30,000 works, including an extensive collection of pieces by Georgia O’Keeffe.
The Pabst Theater Group operates three historic theaters in downtown Milwaukee—Riverside, The Pabst and Turner Hall Ballroom. These beautiful venues attract national touring acts all year long, from rock bands to comedians and lecturers.
Other options: Don’t miss the Harley-Davidson Museum, where you can learn the history of the classic American motorcycle. If you are visiting Milwaukee in late June or early July, check out the dozens of high-profile musical acts playing at Summerfest, the “World’s Largest Music Festival.” Milwaukee is also home to several notable breweries, many of which offer tours and tastings. Stop by the Miller Brewery to see large-scale brewing at work, or stop by Lakefront Brewery for a more laid-back tour.
