dance scene guys enjoying weekend in chicagoIf you’re gearing up and plotting out your guys weekend in Chicago things to do, do it right. Chicago has a lot to offer and you can go just about any party-direction you want. There are a few things you must do and that’s why I’m offering this up. Think of my advice as a broad guide, suggestions and not absolutes. Except for two things, that is. You have to eat Chicago style pizza (both deep dish and thin) and you have to go to a Cubs game (or the White Sox…if you have to). If it is not baseball season, you’re screwed. Not totally. You still have the Bulls, Bears and the Blackhawks. Figure it out.

Here’s Some Guys Weekend in Chicago Things to Do


Guys love to eat. I mean us men love to chow like champions. Chicago is a sweet spot for major chowhounds. Pizza, hot dogs, and Italian Beef. Those are the holy food triumvirate of the Windy City. Okay, great steaks too. If you want to find a great Chicago steak house, click here.

Pizza How You Like It

Let’s get pizza out of the way first. Chicago has ass-kicking pizza whether you want the iconic deep-dish or mouth-watering thin crust.

slice of chicago style deep dish pizzaFor deep-dish pizza, two places for you to consider. Where it all started with deep dish is Uno Pizzeria and Grill at Ohio and Wabash. Be a tourist and wait like a tourist there. Or head to Lincolnwood and enjoy Lou Malnati’s which is another deep-dish veteran.

For thin crust, find an Aurelio’s location. They are Chicago’s oldest pizza chain and you can have it just the way you want it there. Vito & Nick’s Pizzeria on the South Side will make you a true believer.

Hot Dogs and Italian Beef

Chicago has great hot dogs. For Chicago style-dogs, go to Gold Coast Dog on Wabash or America’s Dog on Navy Pier.

While in the Windy City, you have to have an Italian Beef sandwich. Just do it. Go to Al’s Italian Beef in Little Italy or Bari in River West. Both winners.

Chicago Ala-Carte Fun

downtown Chicago outdoor festival crowdWith food out of the way, this city on the shore of Lake Michigan has so much to do. You can take a helicopter tour of the city, visit the Shedd Aquarium, Field Museum, and Adler Planetarium all in one day, catch some comedy at The Second City, listen to blues masters at Buddy Guy’s Legends, or check out the city a glass box in The Ledge which is 1,353 feet up at Skydeck Chicago in the Willis Tower.

If you’re in the mood for naked, pole-dancing women, this town is really not the best. Sure, there are plenty of strip clubs here but instead, you may want to go a slightly different direction.

Pick Up Bars

If you’re in the mood to get laid, which we men usually are…with a vengeance, Chicago just might be your kind of town.

Berlin on W. Belmont is a great joint to hit when looking for someone who’s looking for something. If you’re looking to get laid, Berlin is the place to be.

Slippery Slop in N. Milwaukee is another prime place to hook up. While you’re scoping for action you can score playing Skee Ball too.

Big Boy Beverage Time

Any weekend with the boys involves drinking. It is literally impossible to drink Chicago dry, but there are at least a couple places you want to drink at…if you’re not trying to hook up.

The Hancock Building

Go up to the 95th floor and you will have an unbelievable view of the city, have a seriously stiff drink, and a good meal if you choose. Careful, it’s gonna cost ya.

The Green Mill

Chicago is full of tradition. The cash-only Green Mill on N. Broadway is one of the city’s oldest bars and was a favorite of Capone for goodness sake. Even if their world-class jazz is not really your thing, you need to at least catch a late night set at this Chicago institution.

The Catch All

The Hangge-Uppe club signIf all else fails or if you want to get all your nightlife in one area, hit the Gold Coast neighborhood. With bars, clubs, restaurants and an overall party-hearty atmosphere, you can wander the streets of Rush, Division and State to get your freak on. Here’s where you can party the night away and grab some early morning chow. Hell, you might even get lucky at The Hangge-Uppe that previous night.

Whatever you choose, I hope that you have a great guys weekend in Chicago with these things to do. Men, its all up to you.

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John “Big John” Johnson is a serial fun seeker, a lover of craft beer, and enjoys all things adult beverage related. A dedicated online marketer and SEO, he has been described as “Peter Pan with German Work Ethic”. John is also a sleight of hand magician with serious chops, enjoys riding Harleys, practicing martial arts and travel.

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