Travel Shamelessly in Chicago

Read our Showtime® Inspired City Guide to Chicago

The silver lining to our imperfect lives is that in the cracks and mishaps you’ll find the stories and moments that make this wild ride worthwhile. The characters of the SHOWTIME® Original Series Shameless live anything but picture-perfect lives, but the stories and the shared experiences keep them banded together despite themselves. Not too unlike the Gallaghers, the city of Chicago has such a richer story to share than its metropolitan persona may let on. 

Let Sheraton take you off the L-train to dives and Gallagher-friendly holes-in-the-wall for experiences that will make this a weekend getaway not soon forgotten. Drinks you can toss back, meals you can belly up to, and excursions on a dime, living Shamelessly for a few days will help you take a load off from your usual. Then, kick back in style at one of the five Sheraton Hotels in the Chicago area and tune-in to the newest season on Showtime Sundays at 9pm ET.

Eat Shamelessly 


Portillos – For just $2.85, you can fill up on the best hot dog in town. For that price you get “everything,” which is a fully-loaded Chicago-style dog with mustard, relish, onions, tomatoes, Kosher pickle, peppers, all stuffed in a steamy poppy seed bun.

Francesco’s Hole in the Wall – Gather for a big family dinner of authentic Italian food. The menu changes daily on a handwritten dry erase board based on that day’s fresh ingredients. We’re talking stuffed ravioli in vodka sauce for less than $15!

Chicago Pizza Boss – For a slice of pizza in the heart of the city, look for their giant Italian flag-on-wheels downtown for lunch most days. 

Drink Shamelessly


Brando’s Speakeasy – Don’t be afraid to order two appletinis here, where you’ll find a lollipop in each one! Cocktails, pizza, and sandwiches are served alongside the city’s best karaoke. Perhaps you’ll feel inspired to perform some Nathaniel Rateliff & The Night Sweats. 

Rossi’s Liquors – Locals rave about the “rippin” beer selection at this quintessential dive bar. The old school bartenders only accept cash in this unsuspecting, but satisfying, watering hole. 

Goose Island Brewery Tour – The locals hold a soft spot for this popular brewery. They only recently started hosting tours so you can see how their tasty beers are brewed. For just $12 they run 45-minute tours Thursday-Sunday. You’ll score samples and a custom pint glass.  

Play Shamelessly


Schubas – An intimate concert hall with the coolest bands and macaroni and cheese is all waiting when you dive in at Schubas. Bands play each weekend and tickets are a total score at (usually) less than $15 a piece.

Lincoln Park Zoo – You can’t beat year-round access to the zoo that is completely free! It’s heralded as one of the best zoos in the country and ideal for families or couples to spend a fun day out on less than a dime.  

Belmont Army Surplus – Go thrifting at one of Chicago’s best second-hand stores. At first glance Belmont is a standard Army surplus store; but hidden in its fifth floor is a funky thrift and vintage shop for clothing, furniture, and tchotchke finds that make storied souvenirs.

Hotels featured in this article

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