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top five guide: chicago, illinois

Updated: Sep 7, 2023

Chicago Illinois Skyline from Lake Michigan

Ah, the Windy City! Chicago has been and remains to be one of America's greatest cities. Seemingly always playing second fiddle to New York, it is a crime that Chicago doesn't get more positive press. This may be a hot take, but I generally view Chicago as a friendlier, cleaner, and (sometimes) chillier version of Manhattan.

And this opinion is more informed than you may think. I flew to Chicago for business on a near-monthly basis throughout much of my twenties, and I truly adored every visit (even the winter ones). I did my best impression of a local Chicagoan during those trips, exploring new neighborhoods on foot, using my per diem to try as many restaurants as possible, and jogging off the calories around Lake Michigan and Millennium Park.

It's my hope to turn more people into raving fans of Chicago. I mean, who doesn't love deep dish?

here are my top five tips for a trip to CHICAGO:

The Hoxton Chicago Fulton Market Hotel Room Bedroom

1: where to stay

As a result of my past business trips, I've been lucky to stay in more hotels in Chicago than any other city I’ve visited in the world by far. My favorites are The Hoxton (pictured; boutique vibe in buzzy Fulton Market with a great bar), LondonHouse (great location for first-timers and fantastic 22nd floor rooftop), The Robey (in Wicker Park, one of my favorite neighborhoods; also great rooftop bar), Aloft River North (great budget option with amazing restaurants nearby), and The Blackstone (art deco opulence overlooking Grant Park; also, interestingly, my favorite bathrooms).

Burger from Au Cheval Chicago

2: come hungry, leave happy

Some people may call Chicago an architecture city. Others may call it a sports city. The haters will call it a city in decline (a common refrain I strongly disagree with). If you ask me, I will contend that it is a food city first and foremost. Chicago can truly satisfy any palate, from cheap eats to Michelin-starred meals. Local must-tries include deep dish from Lou Malnati's or Pequod's (not Giordano's!), hot dogs from SuperDawg and Italian beef from Al's. The restaurant scene in general is top notch, and my favorite spots are Aba/Ema, Au Cheval (pictured), Etta, Bavette's, The Publican, and Duck Duck Goat.

Architecture Boat Tour Chicago River

3: architecture boat tour

While I contend that Chicago is foremost a food city, it is also a pretty badass architecture city as well. As a self-proclaimed architecture nerd, I was thrilled to learn that the architecture boat tours offered here are not only one of the most popular tourist activities in the city, but they are beloved by locals as well. Assuming you have clear weather, hop aboard one of the many cruises and learn about the modern masterpieces dotting the skyline today as well as the buildings (and lives) tragically lost during the Great Chicago Fire of 1871.

Three Dots and a Dash Cocktail Bar Chicago

4: speakeasies

With so much good eating to be had around town, it's only fitting that there is some good drinking to follow it up. The River North neighborhood is known for it's nightlife and clubbing scene, though my preference is something a bit more low-key: speakeasies. Violet Hour in Wicker Park is a personal favorite, though you can't go wrong with Lazy Bird at The Hoxton, The Library at Gilt Bar, Blind Barber, or Three Dots and a Dash (pictured; this one isn't really a speakeasy, though technically none of these are because prohibition ended almost a century ago, so who cares!).

Millennium Park Aerial View Chicago

5: millennium park

Look, you didn't think I was going to write a Chicago post without mentioning The Bean, did you? Mark this under the "yes-it's-kinda-dumb-but-you-have-to-do-it" category. While The Bean may be Chicago's most famous landmark, there are plenty of reasons to visit Millennium Park (where it's located) outside of touching the oddball statue. Take a stroll around this pleasantly grassy expanse, be sure to check out the Frank Gehry-designed Jay Pritzker Pavillion, and grab a drink or brunch overlooking the park at Cindy's Rooftop.

You can't always do it all, so one thing we didn't do that I WISH we had:

Go to a Cubs game. You know what's kind of (very) messed up? After at least a couple dozen trips to Chicago, I have still never been to a Cubs game at the iconic Wrigley Field. In some strange twist of fate, I have actually been to a Chicago Dogs game, which is a minor league team, before going to a Cubs game. I am not sure how that happened but I plan to right that wrong on my next trip to the Windy City.

Have a great trip! Feel free to leave a comment with your own favorites. You can also find these recommendations (and more!) in map format by following me on the Out of Office app.


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