March 29, 2016

Chicago on the Cheap

By Sjboatwright In On the Road

If you missed my last post, I gave Chicago the honor of being better than NYC in a lot of ways.  It was easier than I thought given Chicago’s amazingness.  Now I wanted to share a short list of free and/or cheap things to do when you’re in Chi-town yourself.

Get a Cocktail at the Drifter Speakeasy

Chicago was the epicenter of mafia activity during the prohibition.  Even the Capo di Capi (Boss of all Bosses) Lucky Luciano was intimidated by the cities brazen mobsters, commenting that the city was “A real goddamn crazy place! No one is safe in the streets!”

You can get a taste of what the mobsters were at war over in the speakeasy at the bottom of the Green Door Tavern. Upstairs, Green Door Tavern looks like a rundown college bar, eclectic and dark.  Its history is the only thing darker than its lighting (Green doors signified the presence of a speakeasy).

The Drifter is the bar at the bottom of the stairs that lead to the bathroom; be sure to knock before opening the door. The concrete tomb has been restored to its original glory, with vintage cocktails going for $12 a piece. No menus here, just a deck of Toro cards with drinks on them, that way you could pretend you were having your fortune read if Elliot Ness raids the joint.

Catch a Midnight Show at The Green Mill Inn from Capone’s Old Seat



If you know anything about Chicagoland then you’re well aware that the real King of Chi-town was Alfonso Capone. Capone dominated the city’s beer and prostitution rackets, slaying his competitors if they got too out of hand. Capone’s henchmen didn’t make out too poorly either. Machine Gun Jack McGurn bought the Green Mill Inn, a jazz lounge equipped with an escape tunnel behind the bar in case the Feds ran in.

I suggest going on a Sunday and sitting in Capone’s old seat (the wrap around booth that has views of both exits).  If you catch the late show, there’s no cover and the drinks flow cheaply all night long.

Have a Classic Deep Dish Pizza from Lou Malnati’s

Malnati's Pizza

You knew this was coming right?  There’s about a billion places to get a Chicago style Pizza, but Lou Malnati’s father was the creator of the original, and like father, like son.

Take a Stroll on the Chicago Riverwalk

If sidewalks could speak. Although Chicago’s Riverwalk was built in 2001, it walks you past some of the city’s best historical sites. Beyond the Wrigley Building and Tribune Tower, you can wine, dine, and picnic all along the walkway. With a six block expansion to be completed this year, I can only imagine this is going to become a 21st century Chicago icon.

5.) Get in Touch with Your Inner Hipster in Wicker Park


There’s a few places that are so readily associated with hipsterism that you don’t know much else about them.  Chicago’s answer to Brooklyn is the Wicker Park neighborhood on it’s north side. Having spent years in Brooklyn, I can tell you that Wicker gives it a good run for its money. It has all your off-beat, artsy, youth oriented, hipster absurdity.  For $5 at a bar called Pint, you can get a “hipster special”: a shot of an obscure liquor and a pint of PBR.  Perfect, no?  After you grab a quick organic burrito, you can walk off the calories on the Bloomingdale Trail, an elevated walkway complete with modern art, bike lanes, and dragons made from car tires.


Get a Stuffed Pancake at Wildberries

Its going to take you 90 mins to get in on the weekend.  Worth it:


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