24 Hours in Chicago: Near Southside

Whether you’re stopping through Chicago on a long layover or driving through on the way to a nearby state, there will definitely be more than enough to keep you busy. Below is a list of how to have a rockin’ time in the Windy City for 24 hours with options depending on what you want to get out of your experience. Despite choosing some touristy things you just can’t miss, I’ve also added a resident-twist to it. 

This post features the Near Southside of Chicago, including Northerly Island, Chinatown, Pilsen and Douglas Park. Public transportation is not as easy to get around here, so rent a car or Divvy bike, use the CTA bus system or make Uber your bestie. This post is the 2nd part in a series about spending one day in Chicago; the first was a post on the Loop & River North.


Breakfast + Walk

Northerly Island – One of the newest parks in the city, Northerly Island features 91 acres of grass, flowers and trees – a real commodity in the urbanity of Chicago. Pop into a grocery store before you arrive to pick up breakfast items for a picnic on the lawn. Enjoy a stroll along the nature path, walk north along the waterfront or drink in views of the boats and skyline along the marina-front path.




Phoenix – After having lived in Hong Kong, I am a Chinese food snob and so are my friends that live here now, too. Phoenix is up to snuff with the real deal. Grab some dim sum items from the rolling carts, and make sure that you order the xiao long bao (pork soup dumplings) and Szechuan green beans (they’re not on the menu anymore, but they should still make them by special request).

Take a Tour: pick your poison…

Walk on a self-guided tour through Chinatown after lunch, or if you have a big enough group, you can set up a private tour through the Chicago Chinese Cultural Institute.


Lagunitas – Hop in a cab or on your Divvy bike to Douglas Park and the Lagunitas Brewery and Tap Room. They do free tours every afternoon in their colorful and open space.


While on the southside, the National Museum of Mexican Art is not to be missed. It’s free and the art is awesome. It’s open until 5pm every day of the week except Monday, so don’t drink too much A Lil’ Sumpin’ Sumpin’ on the brewery tour.



Murals + Mexican Food

After viewing the art indoors, take it outside with the many murals Pilsen has to offer. The neighborhood is also known for its Mexican food, so eating dinner here is a must. My favorite place moved neighborhoods, but the “downtown” area offers a bunch of delicious options. Choose one of the “best restaurants in Pilsen” on Yelp and you can’t go wrong.





Thalia Hall – If you’re lucky enough to be in town on a show night, purchase tickets to any show just to see this historic landmark.


Before heading to your hotel/hostel for the night, sip on some punch at Punch House (located in the basement of Thalia Hall) or a craft cocktail at Del Toro (order the pineapple sangria!). Both offer an upscale and fun twist to the newly booming/currently being gentrified neighborhood.

Stay tuned for two more 24 hours in Chicago posts: North & West coming soon!

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