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Chicago

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Kasey's Tavern

Arguably the second oldest bar in Chicago, this is a friendly neighborhood pub offering craft beers at affordable prices in a space that's been open since the 1880's in the South Loop area of downtown.

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Chicago is the heart of the Midwest, but it also offers a lot of what makes big cities amazing. A variety of activities, top notch restaurants, world-class museums and entertainment, stunning architecture, and a major airport that is a gateway to the rest of the world. To a lot of people, it’s just a layover, but to us, it’s a playground of possibilities.

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Empire Builder Amtrak Train to Seattle

Most cross-country trains in the USA start and end in Chicago, and the Empire Builder is 1 of 4 routes that will take you from Chicago to the west coast. With a total of 46 stops over the course of 46 hours, you can travel all the way from Chicago to Seattle on one train, but make sure you read this review first so you’ll know what to expect.

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California Zephyr Train to San Francisco

If you want to take a train across the United States, this Amtrak route is the best! You can travel all the way from Chicago to San Francisco on one train, passing through 35 big cities and small towns in-between, but the best part is the jaw-dropping Rocky Mountain Canyons that are only accessible via this train or on a white-water rafting trip on the river below. It’s the most scenic train in the USA and it should be on your bucket list!

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Lake Shore Limited Amtrak Train to Boston

For train travel between Chicago and northeastern destinations like Boston and New York, this route can show you the shorelines of Lake Eerie and some brilliant autumn leaves if you time it right. But beware: which direction you’re traveling in could dramatically change your experience.

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