24 Perfect Hours In Chicago

In Chicago

Springtime is finally here, and that means it’s time to book a trip to Chicago! This Midwest mecca really is a must-visit any time of year, but especially once the winter thaws and the sun comes out. It would be impossible to do everything you need to in only 24 hours, but our contributor, Kaleigh Glaza, is here to help you try!

Here is what to do for a perfect day in the Windy City, whether it’s your first visit or you want to live like a local.

In Chicago 2

Stay

Like a local:

  • The Robey: You only need to make one stop, and this is it. The Robey has only been open for a little more than a year, and is already gaining accolades from publications like Condé Nast Traveler for its welcoming and unique vibe. The rooms are dog-friendly, it has a rooftop pool and has one of the coziest lounges in the city.

For a first-timer:

  • Virgin Hotels Chicago: There is no hotel more fun and full of personality than the Virgin, plus its location right in the heart of the city makes it great for seeing the sights. It hosts boozy tea parties on the weekend, and has a rooftop lounge that’s ideal for relaxing after a long day of sightseeing.
  • The Langham: This one is a splurge, but if you’re only staying for one night, it’s totally worth it! There are epic views of the city, luxurious rooms and it’s also a fantastic afternoon tea spot.

Play

Like a local:

  • Museum Hack at the Art Institute: So, maybe you’ve been to Chicago before and seen all the museum high points. However, this tour takes you through the more unseen parts of the museum. Plus, it’s interactive, so it provides a whole new experience.
  • Emporium Arcade Bar: Venture out of the Loop and into the neighborhoods of Chicago! This old-school arcade bar comes with a host of games including pinball, pool, foosball and all the arcade games of your childhood. Mingle with the locals and have a craft beer while you play.
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For a first-timer:

  • 360 Chicago Tilt: This one is not for the faint of heart! Everyone should go to the top of the Sears Tower (never call it the Willis Tower in front of a local), but this will upgrade your experience by allowing you to tilt out over the building in a glass enclosure, giving you downward-facing views from 1,030 feet up.
  • ANY sporting event: Pick your favorite in-season sport, or your favorite team, and see a game. Chicagoans are a particularly loyal bunch, so even when the teams aren’t winning, it will still be a fun time!

Wine

Like a local:

  • Beatnik: A new and beautiful addition to the city, this is an ideal spot for a girls’ day! The interior is stunning and the cocktails are just what the doctor ordered for a post-dinner relaxing night.
  • Drumbar: Chicago loves its rooftops, and revels in the chance to be outdoors whenever the weather allows. This rooftop is smaller for a more intimate feel, and the bar staff makes some of the most original and tasty sips in the city.

For a first-timer:

  • Cindy’s Rooftop: This rooftop has some of the best views and cocktails in the city. It’s perfect for brunch drinks, and it’s only steps from the infamous Bean that everyone will want to take photos with. Double dose of fun!
  • Three Dots and a Dash: From high above the city to underneath, you’ll get a very different, but no less delicious, drinking experience at Three Dots and a Dash. Enter through a back alley and descend into a tiki paradise for over-the-top cocktails and a crazy fun time.

Dine

Like a local:

  • Stan’s Donuts: Not technically a Chicago original, but surely a Chicago staple. The donuts at Stan’s are fantastic, and the interior and branding are infinitely Instagrammable. Get the Lemon Pistachio and you’ll be perfectly fueled all day long.
  • Ronero: The West Loop is a gold mine of restaurants, but Ronero is special. You’ll feel like you’ve stepped back in time, and been transported to South America just by walking in. The ceviche and Cubano sandwich are not to be missed, and you can head upstairs to the rum bar after dinner.
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For a first-timer:

  • Small Cheval: Skip the line at Au Cheval, and save time by hitting up one of the Small Cheval locations for a seriously boss burger. It’s exactly what Chicago is known for: unpretentious and without frills, but still freakin’ amazing.
  • Lou Malnati’s: We would be remiss to send you to Chicago and not tell you to get a slice of pizza. The tough part about this is that everyone has their own taste and favorite spots! Lou Malnati’s is the most classic version of deep dish, and a favorite of locals. So, you will be able to skip some of the touristy lines by choosing this spot.

Waiting for the travel bug to bite you? Check out some of the trendy hotels we’re dying to visit, and our guide on surviving traveling during the busy holidays!

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  • I love Garrett’s popcorn! That is a must stop whenever I visit the city! Also whenever I fly, I always make sure to catch my connecting flight at O’hare because they have a shop in the airport!! :)

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