Through the Eyes of an Educator: Chicago, Illinois

by Stacey Ebert /
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Jun 06, 2016 / 0 comments

I’ve been hearing about Chicago since I was little. My dad used to go there for business, sometimes out and back in a day. A northern midwest hub of action, business, finance, media, and all things Cubs, this city on Lake Michigan can grab anyone’s attention. Coming from any major city, a visit to Chicago is something similar, yet very different – a simple way to ease into travel if that’s something that is a frightful action for your fellow travelers. The students in our classrooms often run the grand spectrum. With thirty very different humans, all with their own set of ideas, challenges, and fears, there are some who crave the different, others who fear it, some who could care less about it, and a general chunk that are on the fence of travel, change, and the idea of something new. As educators, wouldn’t it be fabulous if these were some of the things on which we could focus instead of testing, data, or the fixation on rubrics? If opening students’ eyes to things other than their norm could be on our daily agendas, perhaps we’d have even more young people interested in seeing the world, getting their feet wet, and with less fears of different. 

Through the Eyes of an Educator: Chicago, Illinois

Each time I have been to this Midwest mecca, it’s been with a friend of mine from Minneapolis. Versed in Midwest jargon and an aficionado of all things cheese curd related, she has been to Chicago many times and was helpful in introducing me to my first Great Lakes experience. With a large downtown area embracing fabulous architecture surrounding lake and river, Chicago pulses with a rhythm all its own. Each time has been a bit different - a lesson gained from travel. Find joy in the same and different while embracing the change. Having stayed in both the downtown area and about an hour away by public transport, Chicago’s diversity of city and suburbs offer options and opportunities of enjoyment for all. Go with the flow, be spontaneous, plan while leaving room for flexibility, find joy in the simple, meet new people, try new things – Chicago has stories to tell and many lessons to share.

Like any major city, there are pros and cons, thriving areas as well as troubled, places filled with glitz while others are still in process. Realizing that even when a particular area is showcased on ER or Chicago Fire it doesn’t mean that it’s the definition of an entire city is an essential part of life. A lesson in the stereotypes, generalizations, and their negative impacts is one that’s never too early to learn. Known also for renowned politicians, celebrities, and comics galore, visitors could play a ‘Who’s Who’ of Chicago for hours. Stand on the tracks of the ‘L’ to marvel at above land transportation. Train fans might want to talk to those who work for the system or check out their well-drawn maps to learn distance, direction, transport options, and more. Journalism fiends will want to check out the Chicago Tribune for history-making reporting that has stood the test of time. Chicago has much to offer and even more to teach.

Upon arrival, travelers will see a city on the water. Already a difference from some coastal locations, Lake Michigan’s fresh water magnificence is one not to miss. Life on a lake, city on a lake, weather changes on the water, along with water safety and entertainment are all conversations that arise out of being near this immense body of water. To entertain the engineers and architect fanatics in your crew, try an architectural tour on the Chicago River. Not only do guests get to see the city from the water and learn about the historical buildings that reside along the edge of the water, but also, there’s the advantage of a lock and dam conversation regarding how boats and ships pass from the Chicago River into Lake Michigan. History buffs, mathematicians, art lovers, design enthusiasts, and more can hop aboard a river cruise, check out the sights of the city from the water, hear about the history of this famed city, and learn more about how ships cross from one body of water to another.

When in Chicago, be all in Chicago. Take the family on a meander down Michigan Avenue. Check out the fancy shops, trendy restaurants, and everything along the Magnificent Mile. Check out the museums aplenty or take your troop on a walk to Soldier Field. Enjoy souvenir shops with Bears, Bulls, Blackhawks, and Cubs everything, or pop into Garrett’s Popcorn to enjoy one of Chicago’s legendary treats – but be sure to remember to use the wet wipe at the bottom of the bag so your orange-infused fingers don’t leave a lasting mark on everything you touch. For more culinary history, check out the home of Chicago Deep Dish pizza. Whether you eat, with a fork and knife, at Gino’s East, Giordano’s, or Lou Malnati’s, bring your hearty appetite to bite into a slice of history. If waiting more than one-half hour for your doughy delight to cook is not your thing, try a Chicago hot dog from any of the myriad of colorful spots around town – be sure to order correctly and get it with the works. 
Deep Dish pizza at Gino's East. From Through the Eyes of an Educator: Chicago, Illinois

Deep Dish pizza at Gino's East

Garrett's popcorn. Through the Eyes of an Educator: Chicago, Illinois

Garrett's popcorn

Travel is more than a plane ticket, roadside stop, or passport stamp. There’s history around the entire city of Chicago. If the buildings could talk, they’d sing with stories of crime dramas, baseball greats, political passion, comic lore, and culinary arts. For the sports fanatics in your party, there are few greater historical spots in the US than Wrigley Field. With its well-known banner hovering high above the front entrance greeting thousands each season, Wrigley is one of the oldest stadiums in the country. Second only to Boston’s Fenway Park, Wrigley’s iconic symbols are legendary. Sporting greats have graced both the visiting and home team locker rooms. Harry Caray called games from the very press booth still used today. This classic stadium fills game after game, including with those who pay for seats set atop the surrounding buildings. Stores around the stadium boast the newest information about each game while tirelessly supporting their team for years on end. This is a baseball town like no other. Whether you’re a fan of the game, the Cubs, or sports in general, book early to check out a tour of the stadium to set foot on that sacred ground. Older generations can relive baseball magic here. Young ones can awe at the mystique of a classic stadium. History buffs and sports statisticians in your group will revel at the multitude of information garnered on the tour. Sports fans will love the feeling of sitting in a major league dugout, watching from the bleachers, and going where no game day visitor has gone before. You won’t be disappointed.
Wrigley Field. Through the Eyes of an Educator: Chicago, Illinois

To take in Chicago at its best, head outside in the warmer weather. Visit Millennium Park for an afternoon of people watching, relaxation, picnics and a visit to the Bean (Cloud Gate), one of the many emblems of Chicago. Wonder with the hundreds of others who will be there with you at the construction, design, and magic of this artistic structure in the center of it all. Wander down to Navy Pier and take in a view of the lake from relaxing chaise lounges or shop amidst the city. Tourism buffs might want to take a look at The Drake Hotel to admire the artistry, history, and design that still stand the test of time. Take in a walk by the Lake, pop your toes in the fresh, clear water, or enjoy a Midwestern sun-filled day on one of the country’s greatest lakes. And in the evening, take your over-21 crowd to Second City Comedy Club. Between sidesplitting laughter and hours of enjoyment, remember you’re sitting in a space that has churned out some of the great minds of comedy, including Saturday Night Live® alumni Tina Fey and Dan Aykroyd. For those who show even further interest, find out more about the comedy classes offered by Second City to try your hand at bringing out your funny.

Cloud Gate (the bean) - Through the Eyes of an Educator: Chicago, Illinois

Chicago has heaps of areas that surround the city. Whether you’re wandering Old Town, hitting up Lakeshore Drive, shopping the boutiques of Lincoln Park, or spending the afternoon checking out Evanston’s Northwestern University, there’s something for everyone. Mark Twain was right – “travel is fatal to prejudice, bigotry and narrow-mindedness.” Grab your kids, family, friends, or just go yourself and make Chicago, Illinois a destination of fun, excitement, learning, and laughter. 

Navy Pier. Through the Eyes of an Educator: Chicago, Illinois

Stacey Ebert, our Educational Travels Editor, is a traveler at heart who met her Australian-born husband while on a trip in New Zealand. Stacey was an extracurricular advisor and taught history in a Long Island public high school for over fifteen years, enjoying both the formal and informal educational practices. After a one year 'round the world honeymoon, travel and its many gifts changed her perspective. She has since left the educational world to focus on writing and travel. She is energetic and enthusiastic about long term travel, finding what makes you happy and making the leap. In her spare time she is an event planner, yogi, dark chocolate lover, and spends as much time as possible with her toes in the sand. Check out her website at for more of her travel musings.
All photos courtesy and copyright Stacey Ebert