The Chicago Series: Chicago’s Best Kept Secrets

chicago alley

Ok, part three of The Chicago Series and I’ve saved the best piece for last. Ya girls searched far and wide, gone through some questionable experiences, all in the name of blogging of course.

These are some of the best-kept secrets in Chicagoland. You won’t find them by looking for them. No. They find you. 

The Wieners Circle

What appears to be just a quirky dive of a hot dog stand in Lincoln Park is actually quite an experience. When the clock strikes midnight (or thereabouts), brace yourself for a round of abuse hurled at you by the waiters. Their trash talk will put anyone to shame so bring your A-game and after a bit of liquid courage and you can heckle them back, making for a hilarious exchange as you wait for your food.

I know what you’re thinking. I’ve always wanted someone to viciously berate me whilst I enjoy my hot dog. Well, look no further than the Wieners Circle. 

If you’re feeling extra cheeky, ask for a Chocolate Shake. No, it’s not a drink. It’s a decent serving of some large knockers courtesy of the women behind the counter. Yep. Those kinda knockers. A $20 tip is required but come on, how many times will you get a hot dog with a side of boobs?

Oh and FYI the dogs themselves are actually pretty good.

wiener circle

Turtle Racing at Big Joe’s

The first rule of turtle racing is you don’t talk about turtle racing. 

The second rule of turtle racing is to form a Pokemon-level bond with your turtle. Get tight. Turtles perform better when they have a connection with their better. Just for the love of god don’t share your pizza with them. That is nay-okay.

If your turtle wins you net a free Big Joe’s t-shirt and entry into the tournament in Las Vegas. Yes. There is a legit reptile racing tournament in Las Vegas. If the bright lights, strippers and slot machines didn’t entice you – you now have a reason to hit up Vegas babyyyy!

The Lincoln Square pub tradition has been going, every Friday, for many years and the owners have no plans of stopping. FYI no harm is done to the turtles, in fact, Chucks, Lola, Swisher, Doozy, Jolanda and Lucky Dan all live very privileged lives.

Oh and the third rule. Keep your wits about you and don’t go betting all your savings OK. You don’t want to tell your other half you plundered the mortgage on a god-damn turtle race.

The Infamous Malort Shot

The Malort Shot is a rite of passage for any Chicagoan.

Known as the..ahem…two-fisted liquor (take that whichever way you want to), rumours of it containing kerosene are completely false of course but the real thing doesn’t taste too dissimilar.

Seriously though. Malort’s two key ingredients are wormwood, a herb which kills stomach worms and parasites and absinthe. Destination: Gagville. Population: You (if you have a shot of Malort).

It was brought over here by Swedish immigrant Carl Jeppson in the early 1900’s, who would sell it door-to-door, eventually introducing it to the ever-growing polish population who in turn, introduced it to the rest of Chicago.

It’s distinctively Chicago and the only liquor to beat prohibition, loopholed as medicinal alcohol. Clever monkey, that Jeppson.

It’ll put hair on your chin, your chest and anywhere else because as their slogan goes “Malort, tonight’s the night you fight your Dad”

So, for those of you ready to say goodbye to a piece of your dignity, here’s the map of venues that serve it. 


Up and Up Rooftop bar @ The Robey Hotel

Not so much a secret, but more like my absolute favey spot in Chicago. Although for all the hype there is about Chicago having the most amazing rooftop bars, you rarely hear of Up and Up. Which is precisely why it has made my list.

With its art-deco architecture and flat-iron structure, the hotel itself has a real charm to it. As soon as you enter you feel like a flapper gal straight out of the roaring 20’s with a cute bob, Mary Jane’s on your feet and a cigarette in your hand.

Head up to the 13th floor and you’re greeted with stunning views of Chicago. From all angles. The Robey is the tallest building for miles so there’s nothing that covers the city skyline and it’s surrounding neighbourhoods. The cocktails are neat, the wines are divine but neither are cheap, so bring your dollar bills and simply enjoy this little hidden gem.

Here’s Simon and I having a good old lol at the schmucks who don’t know about the Robey…

Up and Up Robey Rooftop Bar

The Chicago Pedway

Again, not really a secret as it’s used by thousands of pedestrians every day. But I think we need to give a little more credit to this incredible system of underground tunnels and overhead bridges that link more than 40 blocks downtown. For if no reason other than it gets gnarly cold in the winter so hats off to the city for providing the public with a safe, warm and convenient way to travel around the city. 

The Pedway connects public and private buildings, train stations and includes shops/cafes etc. Some parts are in pretty good shape, and still in their original tact.

For those of you dying to learn more about a footpath (albeit a very cool one) there are tours on every day detailing the history and logistics of the pedway. Pedway on a Segway they’re called. Only joking. They’re by foot. It would be way too dangerous riding around on a Segway.

Medieval Times

For anyone whose fantasy involves interactive jousting and eating chicken with your bare hands – this is your jam.

Located about 40 kms/26 miles out of downtown Chicago, Medieval Times is a hilarious afternoon spent wearing crowns, drinking mead and watching Knights fight to the death. TO THE DEATH. Ha, more jokes. There’s no real violence other than between the single Mum’s trying to get a selfie with the Knights.

Medieval Times


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