Chicago: The Four-Day Weekend

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You’ve no doubt heard all the typical stories about Chicago being the city of big shoulders, how cold it gets in the winter, and deep-dish pizza; but there’s so much more to this truly great American city. 

Yes, Chicago is still a world-class sports town with equally great hot dogs. But in the last decade, thanks to a cultural and tourist boom, it’s become so much more, a city with grand architecture, entertainment, museums, some of the best sports teams in the country, enough room to walk, run, and bike, and one of the best food scenes in America. Unlike New York City, you won’t bump into bags of garbage thrown out onto the sidewalks, and as the capital of the Midwest, locals are more than willing to show you a good time. Just be warned: you’re probably going to eat and drink a lot, so make sure to plan some time to hit the gym in your hotel or skip using the Uber once or twice and just walk. 

Any time but winter Chicago is a runner’s city, with the second biggest (and one of the fastest) marathons in the country, with miles of pristine running space along Lake Michigan. Other worthy running routes include the 606, Chicago’s answer to New York City’s High Line, and the 372-acre Washington Park near the University of Chicago, with its wide sidewalks. In the event that you want to run against the January winds or hot summer day, look into Galter LifeCenter and its indoor track. 

If running isn’t for you, try rowing on the Chicago River. The Chicago Rowing Foundation and The Chicago River Rowing & Paddling Center can point you in the right direction, but prices usually run twenty dollars an hour if you want to go a bit easier and rent a tandem kayak, around $100 if you have a group of friends to go rowing with, or $65 for a private lesson. You get to work out while looking up at one of the best skylines in the world all around you.

Holmberg Glass Bridge in downtown Chattanooga, TN

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People will tell you to get a hot dog or an Italian beef, and we won’t stop you, but there’s so much more to Chicago food than those staples. One of the great steakhouse towns, you can go to a place like Gibson’s for the old-school experience, but Maple & Ash is another option worth checking out for a more modern spin. The dry-aged ribeye is spectacular — and comes with a complimentary gin and lemonade martini, brought to your table as soon as you sit down.

Located in the bustling Fulton Market area, The Publican is a perfect blend of Chicago’s history with the present. The stockyards meets fine dining, with a menu filled with meats and veggies all from farms from within the tri-state area. The pork rinds are famous among locals, and the aged-ham selection is also popular, but don’t overlook the farm chicken served on a plate with hand-cut fries and summer sausage. The Duck Inn in Pilsen also never misses the mark, even with their outrageously good hot dogs. People drive from all over to try the duck, but the secret is the duck-fat hot dog. A tribute to the city’s famous meal in a bun, you will dream of their version made with beef and, you guessed it, duck.

Chicago is a drinking city, and has no shortage of places like Delilah’s or Revolution Brewery to get your fill of whiskey or beer, but for something a little different, Three Dots and a Dash has brought a retro South Pacific feel to the notoriously cold city, serving up Tiki classics like the Painkiller, and the scotch-laced Polynesian Pearl Diver, along with a changing menu featuring some of the most creative cocktails anywhere in the country.


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If you can get the dates you want at Longman and Eagle (warning: they book up far in advance), by all means try and do it. The fact that you’re staying in a building connected to the Michelin-starred restaurant will make your dining choices a little easier. But since those rooms are probably the most popular in the city, Chicago Athletic Association is a great new choice. Looking like something out of the Gilded Age with all modern amenities, and situated across the street from Millennium Park and the city’s famous Art Institute, it’s in the heart of the city, which can get a little crazy (in a good way). If you’re looking for something more centralized, with a little more space to talk around, Virgin Hotel Chicago and The Godfrey are both reasonably priced options that offer great bars that are packed on the weekends, comfortable beds, and are both housed in buildings that are perfect examples of why architecture buffs love Chicago.

Insider Tip
From the electric blues to indie rock, Bo Diddley, Wilco, and Chance the Rapper have all helped make Chicago one of the most important music cities for decades. You can visit Willie Dixon’s Blues Heaven located at the same landmarked spot where Muddy Waters, Chuck Berry, and the rest of the Chess Records roster recorded, or catch a show nearly any night of the week at venues like The Metro or the Empty Bottle. While those are two of the best options, the Bottle recently teamed up with the Longman and Eagle folks to open Thalia Hall in the Pilsen neighborhood, which serves up great shows, and features one of the best new food menus in the city. 

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