In October 2016 we landed in Chicago with Jedidiah Jenkins to explore for 24 hours. Using Hyatt Centric The Loop Chicago as our launchpad, we were up at sunrise to take in everything the Windy City had on offer. A full day later, we collapsed back at the hotel with some unexpectedly unique experiences, huge laughs and even some big wins to our name. 

Ranging from the tourist must-dos to local niche finds, here are some of our recommendations for a complete 24-hour “sunrise to sunrise” stay in the Windy City:

Chicago is known as the Third Coast because of its relation to Lake Michigan. A compass is hardly ever needed because any Chicagoan can always point you East. We started our day at sunrise on Oak Street Beach with some friendly geese. It’s the perfect spot to admire the grandeur of the skyline before heading into the urban bustle.

Follow our lead by starting your day off bright and early at Snaggletooth in Southport, a bit off the beaten path, for the day’s most important meal with a bagel and their specialty, house-cured fish.

Need to get ready for a day of exploring? Another good choice is Longman & Eagle, a popular spot among locals and tourists alike. Located in the heart of Logan Square, head here for brunch (we recommend the cinnamon french toast!) before you depart on a journey to explore this trendy neighborhood full of independent shops, great food and drinks, and other activities.

Wander over to Woolly Mammoth Antiques and Oddities — a whimsical and weird store owned by a husband/wife team in the charming Andersonville neighborhood. From antique posters and neon signs to taxidermy and skeletons, there’s no end to the surprises you can find here. And, just down the block is La Colombe —  if you find yourself in need of a second cup of coffee.

Willis Tower (formerly the Sears Tower) needs no introduction. If it’s your first time visiting, this is a no-brainer. Step out onto the glass floor, if you dare, and look 103 stories (1,353 feet) down at moving toy cars and microscopic people-ants.

Running along Lake Michigan, the Lincoln Park neighborhood is a retreat just north of the downtown area. Lincoln Park itself is both scenic and peaceful, with Chicago’s beautiful skyline as the backdrop. It also houses one of the oldest zoos in the U.S. in the middle of the park, with free public access.

After exploring Lincoln Park, head to Beercade, a classic arcade bar in Chicago’s River North district. Two floors of classic arcade games, a large selection of beers, and some delicious food awaits you. Think you’re too cool for some classic pinball? Take this bar’s advice: “don’t grow up – it’s a trap!”

Then, if it’s not frigid out, stop in to Kaiser Tiger for a craft beer and hang out on their outdoor patio (complete with bocce and shuffleboard). The menu’s not too shabby either.

Another must-see in Chicago lies in Millennium Park. Go for a walk or simply relax and people-watch as the crowds flow in and out of this urban oasis. And, of course, no visit to Chicago is complete without a stop by Cloud Gate, otherwise affectionately known as “The Bean,” by famous sculptor Anish Kapoor.

If admiring this world famous sculpture has you craving more art, head over to the Chicago Cultural Centre directly across the street for a range of diverse and engaging exhibitions, performances, and events. Best of all — it’s free!

To start the evening off right, head to Whirlyball in its hip home of Bucktown.There’s bowling. There’s laser tag. There’s beer and wings. And of course there’s the eponymous game … whirlyball! A mix between bumper cars, lacrosse, and basketball, whirlyball promises to have you screaming, laughing, and doing your best to beat your friends.

Want to go dancing but your nails are a mess? No problem! Grab a drink, pick a color, and get both done at Beauty Bar, a one-stop salon of fun. In the back there’s a DJ booth complete with rotating disco ball that will bring out your wildest, fiercest moves — even on a Wednesday when we visited. If you’re feeling lucky, stick around for a game of Bingo. If you’re as lucky as our fearless explorer friend, Jedidiah Jenkins, you might win big!

Your nails are perfect and you’re feeling confident after your Bingo win! The next logical step is to belt out your favorite songs at some off-the-beaten-path Karaoke. We went straight to Alice’s Lounge to take in a husband and wife run local bar, complete with in-ceiling smoke machine operated via a small switch behind the counter at the whim of the proprietor. Grab a drink, choose your song, and wait for the MC to introduce you. If you’re lucky, he might join you on the mic as he did with us for multiple songs.

And, finally, end your night (or morning) back at your homebase, Hyatt Centric The Loop Chicago, in the heart of the city for at least a few hours of rest.

Photos by Ruben Clavell, Elliot Vernon, and Kyle Peters.

This piece was created in collaboration with Hyatt Centric hotels. The recommendations included here are all our own. To explore Chicago for yourself, check out the city’s newest property, Hyatt Centric Chicago Magnificent Mile.

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