The Best Road Trips from Chicago

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One of the best things about living in Illinois and the Midwest, in general, is its accessibility and the fact that you can get to seven other states in a matter of hours. If the concrete jungle walls start caving in and the urban sprawl feels…

The Ultimate Chicago Bucket List – 22 Things Every Visitor and Local Must Do in Their Lifetime

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Chicago’s food, lake, theater, and arts all contribute to the rich cultural tapestry and there are a number of iconic things to do and signature places to eat that are required to have the quintessential Windy City experience.

A Historic Route 66 Road Trip Across Illinois: Driving from Chicago to St. Louis

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Whether you’re a history buff, motorhead, photographer, road trip enthusiast, or general travel lover, driving Route 66 is a trip everyone should take at least once in their lifetime. Here's how to get your kicks on the Mother Road.

The Best Beach Towns in the Midwest for a Magical Summer Getaway

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Most people think about heading to one of the coasts when they need a beach retreat, but you don’t need an ocean to find an epic beach town. It’s actually the middle of the country that’s privy to some of the most surprising travel gems for summertime fun.

17 Awesome Things to do in Chicago That’ll Help You Resist the Urge to Hideout and Hibernate this Winter

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It’s super easy to want to crank up the heat, bury yourself in a blanket, and Netflix and chill from November through April. But fight the urge because Chicago actually has plenty of year-round attractions, many of which are even better in the winter.

It Wasn’t the Midnight Train to Georgia, but I Did Take an Overnight Sleeper Train from Denver to Chicago

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For some reason, I've found that holiday travel brings out the worst in people. It’s supposed to be a time for cheer, but instead, the airport becomes a place of scrooges, overrun with lines and crowds. People are pushy and curt,…

My Least Favorite Question

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When people meet me for the first time and find out what I do, they generally ask one of two questions: “What’s your favorite country?” or “What’s your favorite restaurant?” Travel is a topic I could talk about all day (and…

Chicago

A Goodbye Letter: Why I Ultimately Left Chicago (But Will Always Love It)

While I regularly complained about the hassles of living downtown (creeps on the El, terrible drivers, the lingering stench of pee), leaving Chicago was by no means an easy decision. Sure, you make choices that steer your direction…