BySheila Dichoso, writer at
Mother of Bulldogs, Queen of Caffeine, Protector of the Pop Culture Realm, Editor at Hulu
Sheila Dichoso

It’s been three years since “Happy Endings” left the air, but in our minds Max, Brad, Alex, Dave, Penny, and Jane are still the perfect TV best friends. They were funny, silly, and constantly dropping pop culture references circa 2011-2013 like it’s no big deal (They were totally obsessed with “Revenge,” too, guys!). And whether life sooked [sic] or was filled with dramaaaa, the gang stuck together through thick and thin.

Another reason why we loved “Happy Endings” so much was because of the seventh member of the gang – (sadly not us) Chicago. TV portrayals of twenty- or thirty-something friend groups figuring out life together usually take place in New York City. But Chicago is dope. It can give anyone who's coming of age the freedom of New York, but with that added Midwestern charm. While realistically the gang’s shenanigans can probably take place anywhere in the world, the city of Chicago inserted itself into the narrative in crazy ways, breathing life into the stories that take place there.

So while Chicagoans probably don’t tell a joke every four seconds and the “Spring Smackdown” doesn’t really signify the end of winter, we still want to buy a one-way ticket to the Windy City to hang with the “Happy Endings” crew. Why, you may ask? Let us tell you:

Rosalita’s Run & Scavenger Hunt: Chicago Movie Edition

Episode to watch: Season 2, Episode 17: "The Kerkovich Way"

The gang’s favorite Chicago hangout serves fab margaritas and holds awesome events, like a Chicago movie-themed scavenger hunt, which includes blowing out “16 Candles,” getting into “Risky Business” at a supermarket, and cooking “Breakfast Club” sandwiches, which all culminates into Max looking into the camera while channeling Ferris Bueller.


Episode to watch: Season 2, Episode 6: "Lying Around"

One of the best things about Chicago is the delicious food of the heavy, artery-clogging variety. Deep dish pizza, heaping piles of beef in sandwiches, dogs with whole pickles on top: This is where carb, meat, and dairy dreams are made. In the show, Dave is a proud owner of a steak sandwich truck called Steak Me Home Tonight which includes a culinary creation called the Steaktanic, a gigantic sandwich that might be “kinda disgusting” and “illegal,” but also kind of appropriate for Chicago. It includes two pounds of steak, a liter of garlic aioli, half a block of smoked Gouda, a head of iceberg lettuce, and a hero roll. If you want to make it at home for some reason, here’s the recipe.

Spring Smackdown

Episode to watch: Season 2, Episode 15: "The Butterfly Effect Effect"

Does the beginning of spring in Chicago mean wearing super cyut shirts? If it does, then we’re in. Every year, the gang knows that the harsh Midwestern winter comes to end because of the “Spring Smackdown” — Jane and Brad’s annual argument that’s so epic, it signals winter's demise. It also brings Max out of hibernation. Welcome to jorts season, y’all.


Max and Dave's loft

Episode to watch: Season 1, Episode 6: "Of Mice & Jazz-Kwon Do"

With exposed brick walls, high ceilings, lots of natural light, thrift store furnishings and so much space, Max’s warehouse loft is every hipster’s dream. It’s no wonder why the gang is always hanging out there. It’s kind of a dump, but with a little interior decorating, it would be Instagram-ready. It’s also perfect for shooting dart guns, hitting piñata, and group jazzercise classes.


"Max's World" Tour of Chicago

Episode to watch: Season 3, Episode 2: "Sabado Free-Gante"

When Brad loses his job and can no longer enjoy his lavish “regular Saturday routine” of shopping and spas, professional hobo Max teaches him how to live in “Max’s World,” aka how to live for free. This all-day tour of Chicago includes stealing doughnuts at an AA meeting, stealing shirts at a home loan fair, and "getting steamed" by standing on a street vent. Chicago is Max’s World, and Max’s World is Chicago.

Mr. Super Gay Chicago Pageant

Episode to watch: Season 3, Episode 20: "The Ballad of Lon Sarofsky"

After Max attempts to pay rent with a barrel of pennies, the gang helps their broke friend compete and win the $1000 prize in the Mr. Super Gay Chicago contest, an annual pageant held at Rosalita’s. 1) This is so much better than getting a real job. 2) Our favorite fictional Mexican restaurant holds the best events.


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