7 Reasons Chicago Should Be Your Next Staycation Destination For Visitors From Wisconsin

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Chicago is one of the most unique and exciting cities in the US, and if you’re one of the lucky residents of Wisconsin, you have this incredible city right on your doorstep. If you’re planning a little staycation this year, there’s no better option than Chicago. The Windy City is renowned across the world for its culture, arts, and food.

7 Reasons Chicago Should Be Your Next Staycation Destination

Staycations can be just the way to scratch your wanderlust itch without needing a big budget. As America’s second city, Chicago is high on most people’s lists of places to visit, so it makes a truly ideal staycation spot. It’s cheaper than many other major cities in the US, like Washington DC and New York City, so that you can enjoy the splendor of the city without the eyewatering price tag.

#1. Take Advantage Of Short Travel Times!

With a staycation, the idea is often to travel relatively close to home – you can’t get better than Chicago if you’re in Wisconsin. Traveling from Milwaukee to Chicago takes less than two hours by car, making it quick and easy to hop from city to city. This means you’ll spend less of your precious vacation time traveling, enjoying more time to spend in the Windy City instead.

#2. Eat Some Of The Best Pizza In America!

If there’s one food that Chicago is known for, it’s pizza. Though it won’t share many similarities with Neapolitan pizza, it is an incredible and delicious dish in its own right. Chicago-style pizza is a deep dish with a thick, mouthwatering base that allows for plenty of cheese and tasty toppings. It’s best to go slow with your first pie – often, a single slice is more than enough to fill up an adult!

#3. Get Active On Lake Michigan!

Lake Michigan is one of the largest lakes in the US and is bordered by four States: Michigan, Wisconsin, Illinois, and Indiana. In Chicago, you’ll find more than enough activities on Lake Michigan to satisfy your sense of adventure and curiosity. You could take a boat out onto the lake, go jet skiing, wild camping or even just bird and wildlife watching. You could also relax on one of the many sandy beaches on the shore of the world’s sixth-largest freshwater lake.

#4. Enjoy Great Deals On Transport!

Traveling from Wisconsin to Chicago gives you some incredible choices for transport. If you don’t fancy the drive, then the public transport options can be excellent, including the Amtrak train that connects Milwaukee and Chicago and runs throughout the day.

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Check out the options on Wanderu’s comparison site to find the best fare and time to travel to Chicago this year.

#5. Travel On The L!

Getting around Chicago after you arrive is super simple – you don’t need a vehicle or endless taxis to get from place to place. Chicago is served by some of the best public transport in the country, including the L, which is the city’s elevated transit system. You can get travel passes for the day or week and enjoy getting from place to place quickly and easily.

#6. Sample The Best Beer In The States!

Chicago is also known for its beer – it is home to more than 160 breweries, which is more than any other city in the US. Chicago also hosts a range of beer festivals throughout the year, so if you’re a real beer or craft ale fan, you should definitely schedule your staycation around one of these landmark occasions. You can find plenty of brewery tours available and beer-tasting tours that take you around some of the most popular beer spots in the city.

#7. Take In The Incredible Architecture!

Chicago’s architecture is well known around the world as being some of the finest that America has to offer. It is made up of a mix of sleek modern skyscrapers, the 20s and 30s art deco constructions and historical buildings dating back to the 19th century. You could spend hours wandering the streets of Chicago in search of new and interesting buildings to see and never run out. A walking tour is a great idea for architecture enthusiasts, which can help ensure you see all of the most famous buildings in the city during your stay.

Wrap Up: 7 Reasons Chicago Should Be Your Next Staycation Destination

Chicago has no shortage of things to do for people who want to explore without getting too far from home. As a Wisconsinite, you won’t have far to travel to get to America’s second city, so you’ll have plenty of time to relax and explore. It is the perfect destination, regardless of the type of holiday you want. Families, couples, friends, and solo travelers alike will all find plenty to love about Chicago. Weekend trips are simple from Wisconsin, but you could also consider a longer stay – you won’t run out of things to do for sure!

What about you, have you ever been to Chicago? Feel free to share any tips & advice below!

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We overland. We eat plants and fungi. We live outside as much as possible. We are all connected. A female travel blogger overlanding and writing about ecotourism, ethical and sustainable travel, socially conscious travel and housesitting. An online travel magazine since 2015.


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