I live in Chicago. Why should I visit Madison? Great question. We're so glad you asked. 

Chicago is connected to nearly the entire world by plane and almost the entire Midwest by car or bus. With that many options, how does a Chicagoan choose where to spend their travel time? Time off is at a premium and budgets are being stretched further and further. That's why we're recommending you take the easy, quick and affordable two-hour road trip from Chicago to Madison. 

We know you have questions. Fortunately, we have answers. We compiled frequently asked questions from Chicagoans about Madison and put them in one place so you can make an informed decision about where you road trip to next.

Jump around to find answers to your Madison questions:

What's the vibe of Madison compared to Chicago?

Madison's vibe can be boiled down to a few words: friendly, vibrant, progressive and chill. The integration of nature throughout the city makes even the most populated areas feel fresh and approachable. There's a law in Madison that no building within a one-mile radius of the Wisconsin State Capitol can be taller than the Capitol, which means you can feel sunshine and open air when you walk through downtown. And the two lakes that flank the downtown region give you space to rest your body and mind. 

One of the most common things we hear about Madison is that the people are just so friendly. There's no way to pin down why Madisonians are so welcoming. But we're really proud of the reputation. Friendliness is contagious and you can feel the smiles spreading when you're here.

How does that compare to Chicago? Our perspective is that Madison is smaller and therefore more approachable than the Windy City. You can cover more ground in Madison than in a similar timeframe in Chicago and it's much easier to find fresh air wherever you are. Both cities provide the down-to-earth mentality the Midwest is known for and both have distinct personalities that locals are very proud of. 

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I am used to a big city. Will I be bored in Madison?

No. Don't let the smaller size fool you; you certainly won't be bored in Madison. Between the outdoor offerings, stellar culinary scene, omnipresent creative culture and the long list of events happening every day, there are plenty of things to do in Madison. 

Some of the most popular things to do in Madison include:

Visitors looking to dive deeper into the best Madison has to offer can sign up for our free Madison Experience Passes which provide on-the-go guides to our craft beverage scene, biking, food, architecture and more. 

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Do I need to bring a car to Madison?

Nope! You can leave your car at home or travel by car and keep it parked at the hotel during your trip. Madison is a very walkable city with several options for public transportation or rideshare options. BCycle e-bike rentals are available throughout Madison and are a sustainable (and fun) way to get around. The city's new Bus Rapid Transit system connects several of Madison's most visited areas in a flash. And rideshare programs like Uber and Lyft are readily available in addition to taxi services like Union Cab.

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What neighborhoods should I visit when I am in Madison?

There are several iconic Madison neighborhoods and streets where visitors can see different pieces of Madison's identity shine. Some popular streets and neighborhoods include:

  • State Street: One of the most famous streets in Madison, a one-mile, pedestrian-friendly street connecting the Wisconsin State Capitol to the UW–Madison campus, lined with shopping and dining. 
  • Regent Street: This stretch connects downtown with Camp Randall Stadium and is dotted with businesses honoring the neighborhood's Italian and Jewish history as well as Badger sports bars and campus haunts.
  • Monroe Street: The Monroe Street corridor begins on the other side of Camp Randall and continues west, skating alongside the Henry Vilas Zoo and Lake Wingra. It's a great street for those looking to do some local shopping. 
  • Willy Street: Known to locals as "Willy Street," Williamson Street has been a neighborhood haven for artists since the 1970s and continues to be a hub for local businesses and creativity. 
  • Atwood Avenue: The city's east side is known for its colorful and eccentric energy, which is evident on Atwood Avenue, home to many local dining spots, a theatre and vintage stores.

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Is the food scene in Madison any good?

The short answer is yes. The longer answer is absolutely yes. Madison's culinary culture is rooted in the Dane County Farmers' Market, the largest producer-only farmers' market in the country. The market is a testament to the community's support of agriculture and local food systems. Everyone from locals to chefs to coffee shop owners and brewers shop at the farmers' market and pride themselves on using the freshest ingredients possible on their menus. This fresh, local mentality is what makes Madison's food scene stand out among every other city that rightfully claims to have incredible food. In fact, the farm-to-table movement is said to have started in Madison, in large part due to culinary pioneers like Odessa Piper, who opened the legendary L'Etoile in 1976, decades before other restaurateurs were considering this approach to food. 

Reverence for sustainability, culture and innovation permeates throughout our local restaurants from street food to high-end dining. In Madison, you'll find more than 40 James Beard honors and more than 100 restaurants featuring global menus with dishes representing nearly every continent.

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What do you do in Madison when it's cold out?

Cooler temperatures do not stop Madisonians from having a great time. Fall is all about nostalgia in Madison. There's fall color chasing, Badger gameday, family-friendly farms and all the pumpkin spice you can consume. Even the crispier fall days can be made warm by embracing all your favorite fall traditions.

We won't lie to you, winters in Madison get pretty cold, but it's nothing that would shock a hearty Chicagoan like yourself. What might surprise you is how active Madison is, even in the winter months. The holiday season is merry and bright with holiday markets and light displays throughout town. January and February are our frozen festival months where we party on frozen lakes and prove that the cold never bothered us anyway. 😉

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