I grew up in Chicago, so to say that I love this city is an understatement. We moved to California when I was fifteen, and at first our return trips to this city were frequent. But as friends and family moved to other parts of the country our visits to Chicago stopped.
About a year ago Jason and I decided it was time to go back. So we started our planning. Since I was all too familiar with the weather, I opted for a fall getaway. Personally, I wouldn’t visit during winter and summer, but instead choose late spring and early fall. In a previous post I outlined the things to do in Chicago’s Downtown or Loop, but here I hope to make a broader case for why you should plan your trip to the Windy City as soon as possible.
Not much time in the Windy City? Here's how to spend 2 days in Chicago.
Table of Contents
The History and Architecture
Poor Mrs. O’Leary and her cow are blamed for the most historic incident in Chicago--the great fire of 1871. This was the myth I was taught in school, but what I did not appreciate until this trip was how this terribly destructive fire led to a great architectural legacy. The widespread use of wood to build structures combined with a lack of building regulations resulted in the destruction of 2,000 acres. One third of the city’s residents were left homeless.
As Chicago began to rebuild it had the opportunity to choose better building materials and begin to implement city planning strategies that would protect people and structures. The original Palmer House Hotel burnt to the ground, but its owner, Potter Palmer, was determined to rebuild and later announced that his new iron and brick structure was “the world’s only fireproof hotel."
Today there are just five structures remaining that survived the fire, and my favorite is the Chicago Water Tower and Pumping Station, now located on the Miracle Mile.
I could write a whole post about the architecture of Chicago, but instead I encourage you to take the Chicago River Cruise when you visit the city--you will not be disappointed. To continue to learn about this city’s history I encourage you to take a free walking tour.
A City Filled With Art
Let’s start with the first and most obvious location for art in this fine city, The Art Institute. This encyclopedic museum is a world class treasure. Not only will you find the most French Impressionism outside of France, but you will find excellent collections from many regions, time periods and artists. Some of the world’s most iconic paintings can be found here including Van Gogh’s self portrait and Wood’s American Gothic.
But this impressive museum is just the start. The city of Chicago is committed to public art which can be found throughout the Downtown as well as in many parks. The famous Millennium Park has space dedicated to rotating public art displays. While we were visiting a series of sculptures by Chakaia Booker were on display. These sculptures were made of old tires and steel and are meant to translate simple materials into complex images.
Art is such an important part of the city that it has dedicated 2017 as the Year of Public Art. This effort includes a $1.5 million budget and the launch of a new annual festival. In fact you could see over 500 pieces of public art located in municipal buildings and spaces throughout the city.
Cool Chicago Neighborhoods
Did you know that Chicago has a total of 77 distinct neighborhoods?
It might take a visitor years to see all these unique places, so needless to say, we only made a small dent in visiting neighborhoods. Based on family history, I opted first to visit Andersonville, formerly the home of Scandinavian immigrants and now a bastion of hip coffee shops, restaurants and boutiques. This was the neighborhood where my grandparents settled when they first arrived from Sweden and Norway.
Next we made our way to Wrigleyville, home of the MLB 2016 World Champions, the Chicago Cubs. Coming from a Cubs family, this side trip was required. We visited on a game day and enjoyed watching the crowds clothed in team gear emerging from the “L” (elevated train that is one of Chicago’s primary modes of public transportation). Even if you are not here to see a game, it’s a fun place to eat and drink and watch the pre-game activities unfold.
A few other neighborhoods we visited purely for the food and bar scene were River North (home of Uno’s Pizzeria) and West Loop (home of the Stephanie Izard empire).
So Much Great Food
I could go on for days about the food in Chicago, so it will be tough to keep this section short. Instead, I hope that if I have not already inspired you to visit this city, then the food scene will be the tipping point.
First, there’s the famous Chicago deep dish pizza. The list of places to try this local specialty are endless, but my personal favorite is Uno Pizzeria & Grill. This place requires patience as you’ll need to wait 45 minutes for your hot, steaming pizza loaded with deliciousness to arrive, but it’s worth it. There are many articles written solely about this topic, so if you are coming to Chicago, be sure to read them.
Next there is the Italian beef and first place goes to Portillo’s with Al’s Italian Beef being a very close second. I’ve never had so much fun eating a dripping mess of hot beef, sweet peppers and soft, dense bread. Both restaurants have many locations throughout the city, so it should be easy to try this second most famous local specialty.
Then there are the large number of fine dining restaurants throughout this city. Excellent chefs--local, national and international--have descended on Chicago and made its dining scene world class.
A highlight of our visit was RM Champagne Salon, a very romantic, dimly lit restaurant located on a cobblestone alley near Randolph Street. Our intention was just to order a drink here and simply check out the place. But we so enjoyed our conversation with the bartender that we decided to order dinner--trout grenobloise and heirloom carrots. Amazing!
I would be remiss if I did not mention the Stephanie Izard “Goat” empire. Her most famous restaurant is the Girl and the Goat which definitely requires reservations a few weeks in advance.
We decided to try one of her more casual restaurants, The Little Goat Diner, for breakfast. Our hotel doorman was very familiar with this restaurant and strongly encourage us to try the Elvis, a waffle topped with peanut butter, bacon, bananas. and maple syrup. This dish was sweet and gooey, and oh so delicious. Clearly Jason and I were not on diets during this trip!
Amazing Public Spaces
Last, but not least, Chicago is home to beautiful public spaces. These spaces often go hand in hand with the public art mentioned above, and the combination is one of the city’s best features. Flanking The Art Institute are Millennium and Grant Parks, and nearby is the very family friendly, Maggie Daley Park. Each of these parks is definitely worth a visit.
And then there is the 18 miles of the Chicago Lakefront Trail along Lake Michigan. We enjoyed an afternoon bike ride along a portion of the trail and were impressed by how many different ways this space is utilized.
Over the course of two hours we witnessed a charity walk/run, several soccer and cricket games, a dog beach, barbecues and picnics. Bikes can be rented at several places along the trail.
This is definitely a city you need to add to your travel “to-do” list. The combination of things to do and places to eat is endless. From its gritty start as a fur trading center, to its post fire building boom to today, this city is constantly reinventing itself and just keeps getting better.