Tattoodo City Guides: Chicago, Illinois

Tattoodo City Guides: Chicago, Illinois

Come inside and learn why The Second City is second to none.

Welcome to Tattoodo Travel Guides, where we take you through the most magical experiences you can have in a city anywhere in the world.

Prepare to stuff your face with artery clogging delights, bust your gut laughing at an improv show, and destroy your liver with one of the grossest concoctions ever created — we’re going to Chicago!

Everyone knows that Chicago is a place that still reveres Mike Ditka as a deity and considers ordering ketchup on a hot dog an offense that can get you knocked out, but it’s also a whole lot more than that. There are world class restaurants, bustling nightlife, and, of course, some truly phenomenal tattoo studios where you can act like a real Chicagoan and get a tattoo of the best flag in America.

Tattoo Studios

1. Great Lakes Tattoo  

Chicagoans care about tradition tremendously, so it should be no surprise that one of their best shops specializes in American traditional work. Owner Nick Colella has been a fixture of the Chicago scene for over 20 years and it shows in this studio. Ever mindful of his roots, Colella has combined all the qualities of the classic tattoo shops of yesteryear with the art forward approach more popular today. In other words, there are artifacts and flash on the walls, but there are also art shows and events in the space. But most importantly, Great Lakes has a tremendous roster of artists cranking out some of the best work in the city. Once you step into the shop you know that you aren’t going to leave until you hear a couple good stories and have a fantastic new tattoo.

2. MAYDAY! Tattoo Company

If American traditional isn’t your thing you only need to wander two blocks down Grand to find some of the sickest realism and new school artists in the country at MAYDAY! Tattoo Company. Owned by Pony Lawson and Gary Parisi, MAYDAY! is an appointment only studio specializing in mind-blowing custom work. In addition to the owners you’ll also find the crazed new school work of Josh Herman and Carolyn Elaine fresh off of a stint on Ink Master.

3. Deluxe Tattoo 

Thanks to being located in a neighborhood with a minimal amount of foot traffic and having an unassuming storefront, Deluxe Tattoo was forced to build their reputation on quality work. And what a reputation they built! Ask almost any Chicagoan where you should get your next tattoo and more often than not the answer is Deluxe. Boasting a crowded roster of talented artists it’s possible to get a tattoo of basically any style you can imagine at Deluxe.

Grab a Bite

1. Pequod's 

Way back in the day when Donald Trump was just an easy punchline and not the possible harbinger of the apocalypse, Jon Stewart lambasted the Orange One for cutting up a slice of pizza with a pair of utensils. But when you head to Pequod’s for the best deep dish in the world you’re going to be forced to use that knife and fork, and we highly encourage it. We could waste our time and have a big argument about whether deep dish is better than New York pizza but that would be silly, let’s just take a second and enjoy the insane deliciousness that is Pequod’s. The golden crust burns at the edges to create a taste explosion that you won’t soon forget. We recommend the sausage and hot giardiniera (just say “giards” if you’re looking to fit in) and a pitcher of something by Half Acre.

2. Kuma's Corner

Satiate your appetite for destruction. While it may be difficult to headbang while you chow down on a massive burger, Kuma’s Corner will make you want to try. The metal bar/gourmet burger joint has two locations in Chicago, one of which has the most metal address of all time, 666 W. Diversey. If every burger was simply named after a band that would be one thing, but each one is a work of art in and of itself, many with subtle nods to the band they are named after. For example, the Pantera has some southwestern flare and the Slayer includes an ingredient known simply as “anger.” They also boast one of the most impressive collections of local micro-brews for those looking to get their drink on. You may have to wait a little bit, but that just helps build up your appetite.

3. The Chicago Diner 

You’ve seen the SNL skit where a Bears loving Chris Farley damn near dies thanks to a Polish sausage lodged in his lung, right? Well, by the end of your trip you will probably feel a bit like that. So it’s damn near time you hit the Chicago Diner and embrace the vegetarian lifestyle. Since 1983 this place has been playing against stereotype and serving some of the finest vegetarian, vegan, and raw food that you will ever find. I consider myself to be a hardcore carnivore and I adore this place. Pro tip — get the cuban sandwich and a cup of the quinoa chili. You will not regret it.


1. Delilah's 

Delilah's feels a little out of place nestled right in the heart of upscale Lincoln Park, but this ain't just any ordinary dive. With over 300 whiskeys at the bar and an impressive lineup of beers from both near and far, there is a little something for everyone. If you're lucky you'll be in town on a Monday when they're serving up $1 American Beer (an actual brand of beer that I highly recommend), $2 Jim Beam, and phenomenal punk rock DJs. 

2. Gold Star

Chicago is often called the City of Broad Shoulders, in reality the City of Bruised Livers might be a more apt moniker. It's a city full of drinkers and there is no more quintessential Chicago drinking experience than bellying up to the bar at Gold Star and ordering a shot of Malort and an Old Style. While there is nothing all that remarkable about Old Style, Malort is an entirely different animal that needs to be experienced, even if that experience is not completely pleasant. This no frills dive has one of the more eclectic (and kickass) jukeboxes in town as it provides the soundtrack to another wasted evening in Wicker Park. 

3. Old Town Ale House 

Have you ever wanted to throw back a few in the same bar Roger Ebert and John Belushi used to spend their entire paychecks at? Of course you do! While the neighborhood around the Old Town Ale House has changed tremendously since they first started slinging hooch in the fifties, this dive has stayed exactly the same. It has a welcoming vibe that is topped off by the hand painted portraits of regulars — both famous and not-so-famous — that grace the walls and the jazz music that will inevitably be coming from the speakers. There is no better way to spend a freezing February night than huddled around a table with friends engaging in conversation and imbibing a few adult beverages at the Old Town Ale House. 


1. The Field Museum

Chicago is filled with world class museums, but The Field Museum stands out for a couple of reasons. First, located a stone's throw from Lake Michigan, the building itself is beautiful and worth taking a trip to even if it weren't chockfull of amazing artifacts. Secondly, it is chockfull of amazing artifacts! From dinosaur bones (like Sue up above) to gemstones to terracotta warriors, their collection is astounding. Lastly, do you like tattoos? Obviously! There is an exhibit running through April 2017 dedicated to the artistry behind tattoos. You can even get inked in their pop up shop at the museum.  

2. Go See Some Theater

From Second City to Improv Olympic to Too Much Light... to the Steppenwolf there are dozens of opportunities to see live theater almost any day of the week in Chicago. It doesn't matter if you are looking for comedy, drama, or something in between, there is a show out there for you. Don't be scared off by little store front theaters either, some amazing art goes on in those unassuming spaces. 

3. Go to the Lakefront!

Chicago is one of the most picturesque cities in the world thanks in large part to its proximity to Lake Michigan. Even during the coldest days of the winter, walks along the lakefront are absolutely gorgeous. On one side you have the water and on the other you have some of the most impressive architecture in the country dotting the skyline. Plus, you've likely been eating and drinking your way through the city for the last couple of days, I'm pretty sure you could use a good walk. 


Sorry for the egregious use of capital letters there, it's still just so hard to believe that the Cubs actually won the World Series after 108 years. Even though the modern improvements have taken away some of the authenticity of the stadium, there is still nothing like spending a lazy summer afternoon in the stands of Wrigley sipping a beer and watching a game. Don't believe us? There had to be something drawing the fans to the park for over 100 years of Cubby ineptitude.  

There you have it, a whirlwind tour of spots to hit in Chicago. And we didn't even include the Frontera Grill, the Green Mill, or the Art Institute of Chicago. Well, I guess you're just going to have to make a second visit. Or a third one, or a fourth one... 

Tattoodo is expanding our Lifestyle section to include Travel, and we’re going to be trotting all over the globe to tell you about the best tattoo parlours and local culture. Interested in your city being featured? Email with the subject line Tattoodo Travel Guides. 

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