Welcome to Chicago, where the city is large enough to swallow you whole and the culture is rich. Here lies the home of many creations, from culinary to educational. You’ll never be bored when exploring this historical landmark! That being said, there seems to be so much to do that you’ll never get it all done, and it’s true: you may not hit every important part on your first visit. Thankfully, this list helps you reach the most essential parts of your Chicago vacation the first time. If you have no idea where to go, or even if you do, consider adding the points following to your itinerary!
Chicago Deep Dish. Three words that rival the New York Thin Crust and rock it to its very core. The traditional traveler may find the Neapolitan in the East, but out West, the big city knows best. The pizza is thicker than even your traditional slice of pie, so “deep dish” is nothing but the truth. They take up to an hour to make if your preferred restaurant is busy, but some will accept early orders so that it’s ready when you sit down, or soon after. In the meantime, don’t be afraid to sit back and relish in your excellent culinary choice.
The rich tomato, the stringy cheese, the thickly-layered crust, all of it comes together in every bite. You can layer it with the most unusual of toppings, or you can leave it plain, but either way, flavor is inevitable. Personally, I say go traditional for your first taste, but to each his own. No matter what, it will be an explosion of flavor and one of the best choices you’ll make in any US city tour. You’ll taste home in Chicago through this dish!
For the people who appreciate history, architecture, design, or any combination of the three, I recommend booking this tour. 90 minutes can fit in an amazing amount of information, and there’s no other tour in Chicago that’s quite as photogenic in that time frame. Almost every building has significance along the banks. You’ll listen to a guided tour from your shaded seat as the boat smoothly slides down the Chicago River. Snacks are served, of course.
From the glass arches to the old-fashioned bricks, everything is important. Everything is historical. Every pane has a story, and every unique design is both new and old to the world in the way Chicago presents itself. Your hour and a half will be quick, scenic, and eye-opening as you discover how essential architecture design truly is. The best part are the pictures: the beautiful shots that remind you of how wonderful your trip really was. Both informative and pleasing to the eye, your river tour will be the perfect addition to your city trip.
American literature at its finest. Even writing has found its place in Chicago. The museum is not meant to show off the best and brightest, but instead, it works to show off all American writers at their peak of influence. Even if you are not an avid reader, you will see something you like in the AWM, as they offer much, much more than the traditional fiction pieces. This place displays everything, from key pieces of journalism to speeches, from nonfiction poetry to lyrics of unpublished songs.
Every piece in the museum is meant to show off the culture, history, and lifestyle of the American public while praising the work that everyone goes through on a day to day basis. Some stories are metaphors, some are completely obscure, and some are written out directly. It is the honorable history of the American people in written word. If you are lost for what to do for an afternoon in the city, take your family and walk through the American Writers Museum. Everyone will find something that they love in this large, beautiful home of writing.
This wonderful event only takes place on Sundays, so if you are not in Chicago during the weekend, you’ll be out of luck. However, if you are fortunate enough to be able to find this event while you’re there, you are in for a treat. Based in one of the city’s most unconventional business areas, the Maxwell Street Market is full of international and unique vendors and stalls to visit. Food, clothing, collectables, and even furniture, it’s all available for purchase by you!
Featuring Mexican and Latin products, the Maxwell Street Market is free to walk, though the experience you get from it is a once in a lifetime chance. You will see vendors at their best, showing off handmade objects or home-grown foods thrown into a dish you never thought you’d want to try. In many senses, this is the traditional marketplace, with people shouting out their wares as you pass by. You’d never expect to see anyone so enthusiastic about food or clothing, but the crowd hype is always large, no matter what time you go. It is only open from 9 to 3, though, and six hours is not a lot of time in the end! Make sure to get there as early as possible so that you can explore every stall!
A classic Chicago tour would never be complete unless you saw the city from its highest accessible vantage point. Put aside a few hours in the day to walk over to the Willis Tower, and ask the man in the lobby to direct you to the Sky Deck. He’ll point to your left, and up you go in an elevator crammed with tourists. The lines may be long, but it makes those minutes in the glass box all the more precious to you. When you do step out into that box, you can dance, lie down, or even jump if you feel adventurous! My father decided that his time would be spent doing push-ups while staring straight down at the city below. Bold!
Pictures are a must, but time is of the essence, so if you don’t get what you wanted the first time, go around and get back in line. Take care that no one is faint of heart in your group, as this particular stop can be shocking! It’s nothing to laugh at. When you get up to that level, even looking directly out can be dizzying. However, if you are the brave sort, and you want to show your family some guts, figure out your moves up on the Sky Deck!
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