Chicago Traveler Blog

Chicago Traveler Blog

5 Chicago Guilty Pleasures You Shouldn't Feel Guilty About

9/22/14 | by

We all have our guilty pleasures, don't we? Sugary, fatty foods, reality television, trashy romance novels. We all indulge, and there's nothing wrong with that. Luckily for us though, Chicago has some of the most satisfying guilty pleasures out there that surprisingly lack a lot of guilt (or at least are well worth it!).

When you're craving something sweet, something greasy or something hearty, even if your diet should object, then dining at many of Chicago’s restaurants can satisfy that. Deep dish pizza is a signature dish that put the Windy City on the world’s map of great foods, and now you can’t visit without a slice of your own. Or at least you shouldn’t. Don’t let your guilt get in the way of you taking advantage of some of the best things that Chicago has to offer, even if these things aren’t doing anything great for your waistline or wallet. You can get back to your health foods and workouts and boring life when you get home, but these are some of the pleasures that you shouldn’t feel guilty about, because they’re the best things to do in Chicago!

The Best Chicago Pizza
Of course when you're in Chicago, you have to indulge. We don't think that you should feel bad about this one, but a few slices of deep dish Chicago pizza is enough to make even the sinner with the loosest morals hit the gym (or at least think about it.) There are a few places though that are so good, and you'll be so stuffed, that there will be no extra room for any guilt! 

  • Pequod's Pizzeria is known to have the absolute best deep dish pizza in Chicago. We can't disagree with the strong feelings that almost everyone has about deep dish pizza with delicious caramelized crust, especially when topped with sausage, but we can definitely pass on the message to anyone looking for a slice or four. The only reason you should maybe feel a little guilty is when you find yourself eating the whole pie. Trust us, it's easier than it looks! Head over to the DePaul area to check it out.
  • Piece Brewery and Pizzeria has great pizza and beer, which is a solid win in our book! What better combination is there? They have great thin crust pizza and interesting toppings to complete your 'za. Mashed potatoes? Clams? Intrigued yet? Comfort food on top of comfort food with a nice, cold, comforting beer along side is enough to get anyone thinking about this Wicker Park restaurant. Try their hand-crafted micro brews. If you have enough, any sense of guilt should fall to the way-side. At least until tomorrow morning.

Sweet and Savory
After pizza comes dessert right? Or maybe instead of pizza? You might feel guilty, but that guilt is so worth even having every meal at Mindy's Hot Chocolate. Lunch, dinner, brunch, AND CHOCOLATE! Actually, desserts of all kind. And they are all delicious. Don't feel bad about indulging in any single thing on the menu in this Wicker Park restaurant, because they are worth every minute in the gym afterwards. And if you've already been here before, you know that they are worth every minute in the gym before too. We've got a little picture of ice cream and donuts taped to our treadmill to remind us of our true goals!

Shopping Sprees
Shopping 'til you drop sounds like a great thing, right? Shopping until your credit score drops is completely different. Spending a day at Magnificent Mile makes even that acquired debt worth it though. Alright, maybe not, but there is enough going on here to do tons of window shopping while still being able to take advantage of some of the irresistible temptations.

Eavesdropping on Others Conversations 
We all do it, don't try to pretend like you don't. Hop on the L for a really interesting crowd or hang out at one of the Chicago bars that are great for people watching. You never know who you'll meet or what you'll see, and the Chicago locals (as well as all the Chicago Travelers) make for one of the most interesting crowds that you'll even run in to. Some of our favorites?

  • Near North: Sip your sangria at Cafe Iberico or relax on the patio at Quartino when you're in the area.
  • Avondale: Hot Doug's. If you like lines and waiting a long time for hot dogs, you will certainly hear an interesting crowd chattering (for a few hours sometimes) and probably complaining, but sticking out the line and riding out the storm like the rest of us. Good troopers! 
  • Wicker Park: Cheap booze and good Tex-Mex doesn't make for any better environment than snooping on someone else's life, does it? Actually, you won't even feel like you're snooping, because most of the people at Big Star will present their business loud enough that you almost feel like you're in the conversation. And if you're in the conversation, you have nothing to feel guilty about. That's how it works, right?

Reality Television
A little part of Chicago that you don't even have to be in the city to enjoy! Catch a rerun (or 10) of the extremely entertaining "Mob Wives Chicago" and "Chicagolicious" to see these feisty ladies hanging out in all your favorite Chicago destinations. The banter and small talk that comes with it isn't all that bad either!

Everyone has their guilty pleasures, and when you're on vacation in Chicago, there's no better time than to indulge in a few of them. Chicago is home to some of the greatest foods, atmospheres and shopping in this country, so pull up a chair, order a second serving and stay a while!

Let us know what your favorite guilty pleasures are that should always be indulged in while you're in Chicago and be sure to follow us on Facebook, Twitter and stay dialed in with us on Google+ for more of the guilty, and not-so-guilty, pleasures of Chicago!