“My first day in Chicago….I set foot in this city, and just walking down the street,
it was like roots, like the motherland. I knew I belonged here.”   – Oprah Winfrey –

Fact:  Chicago is totally underrated. 

As the third largest city in the United States it has so much to offer:  it has some of the best museums in the country, is a culinary hotspot featuring cuisines from all over the world, is home to six major league sports teams, is beautifully located on one of the five Great Lakes, is an internationally renowned architectural gem, and hosts the busiest international airport in the world.

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View of the Chicago skyline from Millennium Park

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View of the Chicago Theatre on State Street


There is a lot to love about this city, but unless you’re from here, most people don’t know much about it.  You probably know who Michael Jordan and the Chicago Bulls are, have likely heard of Al Capone, and may even know what a deep dish pizza looks like.  But Chicago is so much more than that.

Actually, I’ll let you in on a little known secret: the truth is that we Chicagoans like being underrated.  Being underrated allows us a sort of double satisfaction when visitors arrive. Not only are people surprised by what Chicago has to offer, they’re even  more amazed by just how much they love it. If I had a dollar for ever out-of-towner I’ve heard tell me they had no idea just how beautiful Chicago was, I would be a millionaire.

But, we would never make you feel guilty for misjudging our beloved city. No. That’s not how our Midwestern humility operates.  In fact, one of the best things about Chicagoans?  Our general modesty.  We’re big city people with warm, small town, welcoming personalities. We don’t like to be compared to LA, nor to NYC, because, frankly, Chicago is neither.  In the end, the greatest thing about being underrated is that you never run the risk of being called overrated.

The truth is that I love my city whole heartedly and am always eager to talk about it with anyone who asks.  Though I’ve been lucky enough to have lived in six different cities in four different countries, I am, and always will be, a Chicagoan at heart.

Here are a few reasons why you need to experience Chicago for yourself.

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My brother and I as kids on Lake Michigan


Let’s start with my favorite topic: eating and drinking.  (Wait, is this not everyone’s favorite topic?)  Chicago has an enormous restaurant scene.  From New American dining, to creative food fusions, to exotic fare like Ethiopian or Laotian, from local dive taverns to five-star cocktail bars, Chicago has more food and drink variety than you could possibly imagine.  And we have an epic microbrewery scene with places like Revolution, Half Acre, Laguinitas, and Goose Island becoming more and more popular, both in and outside of the U.S.

Like any big metropolis, Chicago is home to a variety of immigrants from all over the world.  This international hub has gifted us with spectacularly diverse neighborhoods spread throughout the city, serving up a huge variety of international fares: Chinatown, La Villita, Pilsen, Polish Downtown, Little Italy, Greektown, Ukrainian Village, North Center, and so on.  These cultural pockets create a unique cultural mix, bringing with them traditional festivals, food, and a distinctive social identity.

Food is so prevalent in the city’s history that every summer for the last 35 years, Grant Park is transformed to showcase Chicago’s dining community at the Taste of Chicago festival.  As one of the largest food festivals in the world, you can eat and drink some of Chicago’s finest while enjoying a variety of live music.  Other festivals include Food Truck Fest, Ribfest Chicago, Chicago Food + Wine Festival… the list is endless.

Chicago also has its very own specialties: Deep Dish Pizza, Italian Beef, and of course the Chicago Style Hot Dog (put everything on it, but no ketchup please!)   Do not miss out on these while you’re in town!

In short, Chicago’s culinary scene is awesome.  Plain and simple.

A few great neighborhoods to visit, and enjoy some killer eats:
West Loop (Girl & the Goat, Avec, Au Cheval, Maude’s Liquor, TETE Charcuterie, Publican)
Pilsen (best Mexican food in the city –  Antique Taco, Nuevo Leon, Kristoffer’s Café)
Chinatown (Lao Sze Chuan, Cai)
River North (Eataly, Lou Malnati’s, Bavette’s, Portillo’s, Frontera Grill)
Avondale (Parachute, Kuma’s)
Logan Square (Longman & Eagle, Fat Rice, Revolution Brewery)
North Center (Bierstub, Half Acre Beer Company)


Art & Architecture

In October of 1871, Chicago suffered a massive fire, destroying thousands of buildings, killing over 300 people.  The city and its citizens suffered a massive blow, and, for a time, were unsure how to proceed.  But the Windy City is resilient, and instead of packing up and shipping out, the community saw this as an opportunity to rebuild, to renew.  The first skyscrapers ever built were constructed in Chicago, and until recent years, it housed the tallest skyscraper in the world. Today, Chicago is renowned for having one of the most beautiful city skylines in the United States, its architectural achievements famous worldwide.

A highlight and must-do when visiting Chicago is the architectural river cruise, a tour offered by the Chicago Architecture Foundation.  A ninety minute guided excursion along the Chicago River will take you past some of the city’s most beautiful buildings, narrated by one of the Foundation’s knowledgeable members. (www.architecture.org, Apr. – Nov., around $45 USD/person) If you prefer something a bit different, places like Kayak Chicago and Urban Kayaks offer city tours via, you guessed it, kayaks!

Complementing its architectural setting, Chicago also has a huge public art scene, overseen by the Chicago Public Art Group.  Internationally recognized, the CPAG is a “coalition of professional artists working to produce high quality public artwork” within the city.  Some of the most famous sculptures and permanent installations include the Picasso sculptures, Cloud Gate (better known as “The Bean”), and Crown Fountain.

Chicago is also home to the second largest art museum in the United States, The Art Institute of Chicago.  Its same-named art is school ranked amongst the top five in the world, with famous alumni like Jeff Koons and Georgia O’Keefe.  The list of public museums is endless: Field Museum of Natural History, Adler Planetarium, Museum of Contemporary Art Chicago, Shed Aquarium, Museum of Science and Industry, Children’s Museum, Chicago History Museum….

To top it off, all museums in Chicago have designated dates throughout the year when they’re open to the public, for free!

Music & Theatre

In addition to the visual arts and countless museums, Chicago has an incredible music and theatre scene.  With numerous music festivals like Pitchfork, Spring Awakening, and the enigmatic Lollapalooza, Chicago is a major destination for touring bands.  The Chicago Blues festival is the largest free blues festival in the world, where greats like B.B. King and Buddy Guy have graced the stage.  Between venues like Metro, Smart Bar, Schubas, Double Door, Empty Bottle… I’ve seen more of my favorite bands in this city than anywhere else.  If you’re a music lover like me, Chicago will not disappoint.

If the theatre is more your cup of tea, Chicago’s live shows parallel those found in New York City. Between the famous Chicago Theatre, the Oriental Theatre, the Broadway Playhouse, and a myriad of others you can see everything from Broadway hits to off-beat indie shows any time of the year.


If you aren’t generally a “city person” and tend to prefer the outdoors, don’t write off Chicago just yet.  One of the great things about Chicago is its accessibility to urban outdoor adventures.  Chicago has everything an outdoorsman in a city could ever want: parks, beaches, trails, gardens, sailing, kayaking, biking, and more.

While it’s no secret that winters in Chicago can be quite brutal (it builds character!) summers in the city are unbeatable.  Located right on Lake Michigan, there are over 26 miles (46km) of public beaches in the city alone, and twice that amount spread throughout the Chicagoland area.  Love to bike, run, or walk?  Then take a tour on the Chicago Lakefront Trail.  Stretching over 18 miles (29km) long, this gorgeous trail runs along Lake Michigan offering spectacular views of the lake, the harbor, and the city’s skyline.  For a unique experience, walk the Bloomingdale Trail, also known as “the 606”: A nearly 3 mile (4.5km) elevated, former railroad line, recently converted to a greenway.   Take in the view as you make your way through three different neighborhoods:  Logan Square, Humboldt Park, and West Town.

On the Chicago River’s south bank, an open air pedestrian Riverwalk offers incredible views of the city, dotted with bars and restaurants along the way.  Places like Grant Park, Millennium Park, Lincoln Park, Portage Park, and Jefferson Park offer massive green oases for those trying to escape the city’s hustle and bustle.   How about outdoor rock climbing in Maggie Daley Park?  No problem!

Plus, with such close access to the river and lake, activities like boating, kayaking, wave running, swimming, and wind surfing are right at your fingertips.  Rental spots are located throughout the city where you can rent almost anything, including kayaks, bikes, sailboats, and even Segways.

If you’re a sports fan, Chicago has something for everyone.  With major league teams in basketball, hockey, baseball (two teams, actually), football, and soccer, not to mention countless minor league teams, you can catch a game at one of the many stadiums, or play a pick-up game at one of the many public fields.  Chicago sports fans are awesome, and we love our teams.  Did I mention that the Blackhawks won the Stanley Cup in 2015?

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Kathy Osterman beach in Edgewater, one of my favorites

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My sister (right) and I (left) out celebrating when the Chicago Blackhawks took home the Cup in 2015

Of course, this list is far from exhaustive, but I’ll let you discover the rest for yourself.  It’s a city is full of surprises and I wouldn’t want to give it all away.

Chicago is an excellent place to meet friendly people, eat some great food, relax on the beach, learn some history, catch a game, and spend a night out on the town.  So ask yourself, really, why haven’t you been?

Welcome to Chicago!

By Julie Rotharmel

Julie is a Chicago area native currently living in Montreal.  She has lived, worked, and studied in Italy, France, Canada, and the United States, working in the tourism and travel industry.  She is currently an Operations Manager at Windigo Adventure, a North American adventure tour operator.  When she’s not busy working, Julie spends her time traveling, recipe hunting, cooking for friends, listening to music, and hanging out with her pet bunny, Bistrot.
All photos used in this article are personal property and may not be reused without permission.

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