Chicago in Under 24 Hours

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Advisor - Gary Gahm
Curated By

Gary Gahm

  • City Travel

  • Food & Wine

  • Weekend Getaways

  • Chicago

  • Local Culture

Advisor - Chicago in Under 24 Hours
Curator’s statement

Chicago is the New York or LA of the Midwest (all while standing on its own, mind you!), and is a city where everyone can find something for them. The biggest names in music, sports, and entertainment frequent Chicago regularly. The food scene is incredible, and the art and culture is something that must be experienced by everyone. Don’t count this as part of “flyover country”, or you will be incredibly disappointed and will miss out on some incredible experiences.

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Where to stay in Chicago

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Things to do in Chicago

Dua Lipa at the United Center

Find unexpected, unassuming restaurants! My best friend and I were roaming around Michigan Avenue and hadn’t had lunch yet. We walked past a place, The Exchange, and weren’t quite sure what we were getting ourselves into as we assumed we were severely under-dressed even for lunch. We entered into a very unassuming entryway/bar and were blown away by the atrium seating space and the menu!

Do the touristy things! I had never been to Chicago before and we were there for a quick overnight to see a concert at the United Center. Before we got checked into our room, we went to explore Millennium Park and the lakefront. I, of course, had to get a picture in front of The Bean, and I have zero regrets. Is it cliche? Yes. Did I do it anyway? Absolutely! Take the time to explore the amazing pieces of art, enjoy the street performers, grab a Chicago Dog from a street vendor. And if you’re a fan of Nutella, make sure you line up early for the Nutella Cafe -- the banana bread is the best banana bread I’ve had in my entire life!

Explore the art and culture that the city has to offer! With so many museums and other incredible places to visit (Shedd Aquarium, Navy Pier, the Adler Planetarium’s Doane Observatory) while in the city, make sure you are intentional in your planning and make sure you bring some comfortable shoes. Whether you’re checking out some of the most renowned art pieces in the world, stepping back in time at the Field Museum, or want to learn what $1 million looks like at the Chicago Fed Museum, you’re sure to be in for a treat.

Chicago might just be the spot for entertainment in the Midwest. With multiple venues in the city (United Center, Wintrust Arena, Soldier Field), you’ll likely have your choice of amazing concerts and/or live sports to choose from. We were in town for a concert at the United Center, and to be in one of the most storied sports venues in the world (shout-out Michael Jordan) to see one of the most famous singers in the world today, it was an incredible time to say the least.

Walk as much as you can when you’re able. Yes, the city is incredibly pedestrian-friendly. Yes, there is traffic everywhere. But to be able to get out and see the city, to explore the city without seeing it all fly by in a rideshare or taxi is the only way to do it. If you’re tired or need a rest, there are plenty of places to stop, grab a bite, or drink, and people watch and recharge. There are also pedicabs galore, so you are almost sure to find another way to get your tired feet to your end destination, if that’s what you should choose to do.

Places to eat & drink in Chicago

Deluxe Burger, The Exchange

  • The Exchange, located on Michigan Avenue, is very unassuming from the outside but opens up to incredible seating options inside. From the welcoming bar area to the grand atrium seating, and the private dining areas, paired with a small yet robust menu, this restaurant will not disappoint.

  • The Nutella Cafe is every hazelnut and chocolate lovers dream come true. Get there early if you’re not a fan of a line that’s sure to stretch down the block and prepare yourself for an overload of rich flavor. From made-to-order crepes, waffles, and coffee (yes, coffee with Nutella -- you’re welcome), you’re in for a treat. Do you want to get a personalized jar of Nutella? You can get that here, too!

  • Kilwins, even though it’s a franchise, has a wide variety of sweet treats that’s sure to please everyone! From incredible chocolates to fudge and ice cream, the flavors (even the incredibly popular Dubai Chocolate) are mind-boggling. Do you want a dipped marshmallow? Great, you can have it. Want some coconut clusters? Have that, too! Hazelnut not your thing, but peanut butter is? Check out the peanut butter & chocolate fudge!

  • If you’re a popcorn lover or know someone that is, you have to visit Garrett Popcorn Shops. (If you don’t get to one while you’re in the city, visit one at the airport!)

Need to know

  • If you’re going for a specific event, try and find a hotel that’s in the general area of where you’re going.

  • Get familiar with the neighborhoods of Chicago, so you can make your “must-visit” list.

  • Bring your patience if you’re driving, as the traffic can get quite intense in downtown Chicago. Traffic flows smoothly enough, but if you’re not used to the “big city traffic”, it can be a little trying on the nerves.

Advisor - Gary Gahm

Travel Advisor

Gary Gahm

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For more travel inspiration and insider recommendations, check out our Chicago page.