GO TO CHICAGO

The Windy City.  Second City.  Chi-town.  The Third Coast.  There are a lot of nicknames for Chicago but I always think of it as my kind of town.  I’m biased.  Chicago is one of two hometowns I claim as I lived there for most of the first ten years of my life.  I travel there often to see family and it is, hands down, one of my favorites.  There’s a pulse to the city that I can feel when I land at Midway or O’Hare.  

Why is Chicago great?  The people?  The cultural diversity?  The architecture?  The elegant grid of the city layout?  The food?  The music?  You can pick any one of these and add a dozen more reasons why Chicago is a place to travel.

ABOUT CHICAGO

I did a little research on this and the name “Chicago” derives from how the French interpreted the Miami-Illinois word sikaakwa which refers to a plant and a skunk.  This may referred to wild garlic that grew in the area.  The first settler was Jean Baptiste Point du Sable who built a farm near the mouth of the Chicago River and Lake Michigan in the late 1780s.  By 1795, Native American tribes ceded the land to the US military and Fort Dearborn was built thereafter.  

In 1829, the city began to take form in the grid-like configuration we know today.  The city became a transportation hub and drawing Yankee settlers who wished to take advantage of the fertile farmlands of Northern Illinois.  In 1848, the Illinois and Michigan Canal opened which created a shipping lane from Michigan all the way to the Mississippi River and then to the Gulf of Mexico.  Due to is central location and water access, Chicago became a transportation hub for not just shipping but for rail and other transport.  The population exploded from the 1840s forward.

In 1971, the Great Chicago Fire claimed the lives of 300, destroyed 18,000 buildings and left a third of the city’s population homeless.  But Chicago survived and the city was rebuilt.  From the ashes of the fire, the city that we know today began to form.  Along with New York, Chicago was one of the first cities to build skyscrapers.  Along Lake Michigan and along the curve of the Chicago River, the thriving city began to form.

By the mid-20^th Century, Chicago saw a flood of World War II vets and displaced immigrants from Europe.  This created an economic boom for the city Skyscrapers continued to be built.  In 1974, the Sears Tower (current called Willis Tower) was completed.  The Sears Tower was, for several years, the tallest building in the world.

Today, along the mosaic of skyscrapers and architectural masterpieces, stands a city weathered by time but aged to perfection.  The people of Chicago are a patchwork of ethnicities and languages that all blend together to call themselves Chicagoans.  As the third most populous city in the US, the Chicagoland area boasts a population of 9.41 million residents according to the 2020 census. 

CHICAGO CLIMATE

Summers in Chicago are hot and humid with daytime average temperatures in the 80s and 90s.  Spring and Fall are short seasons with milder temperatures.

Let’s talk about winter in Chicago.  It’s cold.  The winds off Lake Michigan are some of the harshest blasts of cold air you will ever feel.  Snow is a common occurrence and the city is built to withstand reasonable accumulations.  Blizzards will shut the city down.  Fun fact:  I remember the winter of 1985.  I was a little kid bundled up in a snowsuit and about twenty layers of clothes.  For years, it stuck in my mind that the temperature, not windchill factor, was -30 degrees.  When I told that story, it sounded like an exaggeration.  Nope, it happened.  It was negative 27 degrees in January of 1985 courtesy of what we later learned was a polar vortex.  Dress warmly, my friends.  

WHERE TO STAY

Chicago is a massive city that is sprawled out over 234.53 square miles.  I don’t know that anyone will want to go to the suburbs so I will stick with the downtown area.  Where to stay in Chicago?  I like to be close to the subway, or as we call it, the “L” to get around the city at ease.  I think you have to balance budget and proximity to activities to decide your best place to stay.  

River North.  A lot of nice hotels.  There are amazing restaurants in River North.  Bavette’s and Frontera Grill are standouts.  

Loop.  This is the area I tend to stay as it places you in a central location to get to everything.  Chicago’s Riverwalk and the theater district are in The Loop along with Millennium Park and other architectural standouts.  

West Loop.  Very trendy and upcoming area with tons of eclectic restaurants.

Streeterville.  Close to Navy Pier and Magnificent Mile shopping area.

South Loop.  Up and coming area that has been revitalized in recent years.  South Loop is close to the museum campus where the iconic Field Museum, Adler Planetarium, Shedd Aquarium and Soldier Field stand.

I think the The Loop, named for the loop of elevated tracks where the L runs, is prime location in Chicago to stay.  You are within walking distance to almost every major attraction except Willis Tower and close to the lakefront and riverfront.  

CHICAGO FOOD

People on deathrow are given their choice of what meal they want as their “last meal.”  While I hope I never get placed into a situation where I have to pick my last meal, if I did, it would probably be an Italian Beef, baptized in gravy, with sweet and hot peppers, a Chicago-style hotdog, and a side of crinkle fries with a cup of cheese sauce.  I could not be more quintessential “Chicago” if I tried.  Chicagoans take their “beefs” seriously.  I had a recent discussion about a Middle Tennessee restaurant claiming “Chicago-style” foods.  They get it close.  Really close.  But it’s the thinness of how they cut the Italian Beef sandwiches.  Much like Italy has “DOP” products that you know are made there, I think beefs should be cut to a specific millimeter to be considered from Chicago.  

Who has the best?  Not only Italian Beef but hot dog?  My choice is Portillo’s.  You can ask someone else and their opinion will range from Al’s to Tony’s to Buona’s.  The takeaway is to make sure you eat a Chicago-style hotdog and Italian Beef when you visit.

Italian.  Sigh.  I took my husband to Chciago for the first time in 2016.  We went to a real Italian restaurant.  Mind blown, he refused to eat Olive Garden for the next year.  Everyone has a favorite.  Stay away from the chains and visit local establishments.  

What about everything else?  Chicago not only has its famous deep-dish but it also know for it’s thin crust pizzas.  Cheesecake.  Eli’s cheesecake on the northwest side is worth a trip.  And they ship nationwide!  There’s delis, there’s gastro-masterpieces like Alinea, Frontera, Girl and the Goat, and Bar Mar.  For whatever reason you go to Chicago, enjoy the food.

CHICAGO TRANSPORTATION

It’s a drivable city – if you know where you are going.  I visit family on the northwest side so a vehicle is always a necessity for me.  Can I get around Chicago without a car.  Absolutely.  Taxis and rideshares are very common.  And Chicago has one of the best mass-transit systems in the world called the Chicago Transit Authority (CTA).  

From both O’Hare and Midway, the L subway line can get you to the heart of downtown Chicago in about 30-40 minutes.  The subway lines are color coordinated and easy to follow.  You can buy a pass to cover 1, 3, 7 or 30 day periods that will give you unlimited access to the L and bus routes.  For best information, go to transitchicago.com for information on routes, fares, and trackers.  

WHAT TO DO IN CHICAGO

Everything.  There’s so much.  

My favorite recommendation is to take an architectural cruise on the Chicago River.  It is the best experience and will teach you so much about the history of Chicago and the architecture of the city.  If you can plan your trip around the golden hour, it’s spectacular to watch the light play off the buildings.

Sears Willis Tower.  I can’t help it.  Once the tallest building in the world, the Willis Tower stands like a beacon.  As a child, I remember peaking around corners and buildings hoping I could see it from a distance.  It’s iconic and worth the trip to the top.

John Hancock Center.  Located on Michigan Avenue and not as tall as Willis Tower, the Hancock building’s view is – unpopular opinion – better that the Willis Tower.  You can see up and down the Gold Coast of Chicago.  If it is your first time, go to Willis. If you have time, go to the Hancock Center.

Museums.

Lakefront.

Riverwalk.

Shopping.

SWEET HOME CHICAGO