Beginner’s Guide to Chicago – How to do Chicago Right

on Sep1

1 September 2017 | 6:43 pm

Beginner’s Guide to Chicago – How to do Chicago Right

When it comes to Chicago there’s always so much to do. Especially when the weather warms up and people are out, festivals emerge and the fun begins. Although I’ve only lived in Chicago for the last four years, I’ve had many visitors come to visit and have nearly perfected the “first-timer Chicago experience.” So here’s a tried-and-true way to show your guests around and have some fun yourself.

First, I like to plan most of my vacations in general and my “staycations” around food. Food is not only essential to sustaining life, it’s an important part of any vacation, because it allows you to experience that area’s culture. In many parts of the world including the United States, food is an important way to showcase your culture. While the Midwest is still a part of America, it has its own ways of expressing itself. Most people associate Chicago food with hot dogs and deep-dish, and while I feel it’s important to show visitors the best hot dog joints and pizza in the city, I love showing them neighborhood classics as well.

For first timers looking for good hot dogs, I used to take them to Hot Dougs, but now that they’re closed we go to Devil Dawgs. Devil Dawgs is a good little hot dog joint that has great cheese fries, greasy burgers and obviously great hot dogs. I love it here because they have the classic dog as well as creative takes, and my favorite the Elvis burger which consists of cheese, peanut butter, bacon and sriracha sauce. They have three locations: State Street, Lincoln Park and Wicker Park, giving you a good spread of options to eat in different areas.

If you’re keeping with the classics and your guests need the best deep-dish pizza, my go-to is Giordano’s, although I’m sure I’ll get some resistance from Lou Malnati’s diehards. Giordano’s is my favorite because in my opinion they have a better sauce-to-cheese ratio and I like their butter crust better. If you have guests that want to experience pizza in Chicago a little differently, take them to Chicago Pizza and Oven Grinders. CPOG is amazing pizza, close to the deep-dish style, but a little more unique.

Chicago being a city of neighborhoods gives us such an advantage to show visitors “the real Chicago” or the Chicago we live on a daily basis. I grew up in Las Vegas, so when visitors ask me if I go to The Bean all the time or shop on Magnificent Mile, I equate it to living in Vegas and going to The Strip for fun.   It’s just something you do when you have guests in town or if you work in that area you see it, but you don’t go there for the fun of it. Especially not when there are so many things to do in the neighborhoods. My go-to stops on the neighborhood food tour would have to be Bang Bang Pie and Biscuits and Stanley’s for breakfast. Reno, Blaze, Nini’s Deli and Capriottis for lunch. For dinner – Small Cheval, Furious Spoon, Trike or Parson’s Chicken and Fish. And lastly wash it all down with dessert from Miko’s Italian Ice, Jeni’s Ice Cream or Tastee Freeze.

Here’s what’s important to include in a first-timer’s visit to Chicago. The Bean is a must. It’s iconic and if someone’s never seen it in person then chances are high they’ll want to see it and take photos for their social-media pages. Another place I like to take guests is on a walk to North Avenue Beach along the lakefront path. Not only is it a nice walk – you also get one of the best vantage points of the cityscape on North Avenue Beach. Navy Pier, Lake Michigan and the skyline are all beautifully displayed from the beach. Other must-see sights include views from the Signature Lounge inthe John Hancock. If you or your guests want to experience a breathtaking view over a cocktail, I can’t recommend the Signature Lounge enough. If your guests are a little more adventurous, take them up to 360 Chicago and experience the Tilt that tilts the glass towards the ground for an even better view.

Another super-touristy must-visit is Navy Pier. Now with a newly-installed ferris wheel, the views are betterthan ever. If you get the timing right you can take a ride near sunset to capture a beautiful sunset over the skyline, a truly remarkable sight. Now visiting museums or the Frank Lloyd Wright home and studio might not be for every guest, but they’re definitely worth visiting if guests are into that sort of thing. The only problem with making museum trips is if guests don’t want to see them very much – they take up a lot of time and can be on the pricier side. So I don’t push going if they don’t seem into it. I do love visiting museum campus and I enjoyed seeing the Wright home and studio very much.

Planning trips and vacations has always been fun for me, but I get that some people aren’t planners and like to “wing it.” Whatever floats your boat as long as you get to experience the things you want to see and do, by all means do them on your own time. But with short weekend trips I highly recommend making an outline of a plan so that everyone is satisfied. Happy staycationing everyone! Always be on the lookout for more fun things to do and experience in this great city.



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