If you had two weeks to travel around the U.S., which cities would you include in your itinerary? Most people would answer New York, LA, Las Vegas, San Francisco, or Washington, DC, as these are among the top ten most visited and popular cities in the U.S. Many also enjoy visiting Chicago, the third-largest city in the country. If you choose to stop by Chicago, don’t miss the chance to take a road trip or sightseeing trip to Madison, a lively city with four lakes nearby.
Chilling Out in Madison, Wisconsin – Just 2.5 Hours from Chicago!

Madison, the capital of Wisconsin, is a perfect weekend escape, especially if you love nature and are looking to unwind. Known as “The City of Four Lakes,” Madison offers four lakes ideal for relaxing or water sports, along with a vibrant city atmosphere and culinary options like beer and cheese. From Chicago, Illinois, Madison is a scenic 2-hour 20-minute drive away. When I visited Madison, I came from Appleton, Wisconsin, which is a 2-hour drive as well.
You might wonder where the name “Madison” comes from. If you’re into U.S. history, the name might ring a bell—it’s named after James Madison, one of the Founding Fathers and the fourth U.S. president. Madison was chosen as Wisconsin’s capital in 1836, the year Madison passed away. Not only is the city’s name steeped in U.S. history, but many of its street names honor the 39 individuals who signed the U.S. Constitution.
I traveled to Madison in the winter, just like when I visited Chicago. Surrounded by lakes, Madison can get extremely cold in winter. The winter temperature can reach -17.8°C with heavy snowfall, while in summer, it can hit 32.2°C. Before planning your trip, you should check the weather. I was lucky to visit in early winter, so it wasn’t as cold yet, but I still needed a heavy coat, mittens, and winter shoes to combat the frigid air and gusty winds, especially near the lakes.
Things To See & Do in Madison, Wisconsin
1. Visiting The Lakes

Known as “The City of Four Lakes,” Madison offers must-visit lakes. I visited Lake Mendota, which is close to Capitol Square, Madison’s central business district. The other lakes are Lake Monona, Lake Waubesa, and Lake Kegonsa. I visited Lake Mendota in winter, so I could only sightsee because of the cold. However, if you visit in summer or other seasons, there are plenty of activities around the lakes, like paddle boating, canoeing, sailing, biking, or simply relaxing on the beach.
2. Wisconsin State Capitol

Madison’s most recognizable landmark, the Wisconsin State Capitol, resembles the U.S. Capitol in Washington, DC. This building houses the offices of the Governor, Legislature, and Supreme Court of Wisconsin. You can join a free tour inside the Capitol from 8:00 am – 6:00 pm (weekdays) and 8:00 am – 4:00 pm (weekends and holidays). Don’t forget to explore Capitol Square, the heart of Madison’s central business district. Here, you’ll find restaurants, shops, festivals, and a lively nightlife with bars and music venues.
3. Bandung Restaurant

If you’re craving Indonesian food in Madison, Bandung Restaurant is a must-visit. It serves familiar Indonesian dishes for lunch and dinner, like nasi goreng, mie goreng, sate ayam, lele, ikan rica-rica, tempe stir-fry, grilled duck, and chicken opor. They also offer vegan and vegetarian options like tempeh satay, gado-gado, tempeh sambal, and papaya sambal. The street food options include tempeh fries, fried tofu, pempek, and martabak telur. Prices start at $8.95 per dish. They’re open for lunch (Monday – Friday 11:00 am – 1:45 pm) and dinner (every day 5:00 pm – 8:45 pm). For tempeh lovers, they make it in-house, ensuring an authentic taste.
Bandung Restaurant
600 Williamson St, Madison, WI 53703
4. University of Wisconsin-Madison

This prestigious U.S. university is worth exploring when visiting Madison. The campus is expansive, and you can even catch the university’s famous football team, the Badgers, in action.
5. State Street

State Street is a nightlife hub for the University of Wisconsin-Madison. This pedestrian-friendly street connects the University of Wisconsin-Madison with Capitol Square and is filled with restaurants, cafes, bars, and even a Broadway theater, the Orpheum. Each year, it hosts Madison’s Halloween celebration, Freakfest.
Doesn’t a trip to Madison sound exciting? Although not as big as Chicago, Wisconsin’s second-largest city has its unique charm, making it well worth a visit. From Madison, you can also combine your trip with a visit to Milwaukee, home of the NBA’s Milwaukee Bucks. Madison is about a 1-hour 15-minute train ride on Amtrak to Milwaukee, or you can take a quick bus ride with Megabus or Greyhound.