When I was lucky enough to head to a work conference solo (which I know how to rock), I wanted to also take my own advice and use the opportunity to see a little bit of Chicago. I had a fantastic four-day visit to Chicago, exploring during my conference breaks, and loved my experience.
Chicago impressed me and I couldn’t believe I hadn’t been to this city before. I know Washington, D.C. very well, I love New York, and thought I would move to Boston for a time… but Chicago made its way onto my list of Top American Cities (which is an unofficial list that absolutely no one has asked for).
Chicago is America’s third largest city, with a population of almost 3 million people. Yet it doesn’t feel that big.
Chicago has a fascinating history (with World Fairs, gangsters, a great fire, and so much more). It is a place where history captures the imagination and also informs who it is today.
Immigration and immigrants have profoundly impacted Chicago’s culture and the way the city is structured. And Chicago is quite proud of its welcoming reputation, even though I am sure the melting pot also causes a host of challenges. For example, right now, as the governor of Florida ships refugees to Chicago, Chicago is working to expedite green cards, offer housing, provide social supports and generally integrate the new Chicagoans as best they can.
Lifted directly from the Office of the Mayor:
...immigrants play a crucial economic role in Chicago. Immigrants are more likely to be entrepreneurs in the city, with 39,000 immigrant-owned businesses generating $659 million in 2016.
and
The Illinois Refugee Resettlement Program facilitates relocation and economic self-sufficiency to people who are victims of political and religious persecution that have been granted the legal right to rebuild their lives in the United States. Illinois resettled a total of 724 refugees in 2018. Half of all refugees were children under age 18. The top five countries of origin were Burma, Democratic Republic of Congo, Ukraine, Afghanistan, and Iraq.
But while Chicago struggles to adapt to the influx of people, the diversity of cultures and backgrounds greatly impacted what I experienced on my trip. Classic restaurants from different cuisines have been Chicago institutions for years. The blend of ethnicities is felt in this city in a way I haven’t experienced it in others. There is a fierce identity with cultures and traditions from overseas while also pride in the American spirit and American innovation. Chicago is unique.
Other things about Chicago to love!? The skyline, the architecture, the art!
Chicago is located on Lake Michigan but, in accordance with decades-long legislation on the books, no development can happen along the waterfront. Waterfront is reserved for public parks.
Additionally, Chicago instituted a “Percent-for-Art-Program” which means that 1.33% of all construction project budgets on public buildings has to be allocated to public art and/or city beautification. It shows and it makes a difference!
With all the amazing things to do in Chicago, it can feel a bit overwhelming to know how to spend a short visit. I felt decision fatigue when it came to restaurants and, also, I wanted to be sure I didn’t miss anything.
Here are eight things I ended up doing in Chicago, why I loved them, and why I am recommending them:
8 Great Things to do in Chicago
Go on a Food Tour
I booked a food tour with this company while in Chicago. They give tours worldwide, but this was my first experience with them..
My first food tour was in New York City, but I fell hard for the combo of history, walking tour and good eating in Iceland.
This Chicago food tour did not disappoint!
A telling testament to Secret Food Tours of Chicago? Those who joined me on a tour had been to Secret Food Tours in other cities and kept signing up for them wherever they went. A repeat customer is a good sign.
The actual food component of the Secret Food Tour was great. We were able to try all of the classics, without having to decide where to go. We also received a history lesson at each stop as to why it was chosen and how its food had shaped Chicago.
But this was also a walking tour of the sites and buildings in the area. Our guide walked us through buildings of note, while, of course, explaining why they were notable. The walking was a nice antidote to all the food, but it also provided access to and an understanding of Chicago that I am not sure I would have had otherwise.
AND of COURSE there was a “secret” stop. I am not ruining the surprise here, but there was a secret stop on the food tour!
In the end, we had so much food (I was stuffed when we finished), and I tried things I had never had before (that I don’t know if I would have otherwise tried). We learned the secrets and history of deep dish pizza, learned why a particular popcorn blend is so important, were told how Italian beef was developed and, of course, tried a Chicago hot dog (without ketchup) among other things.Â
Visit the Parks - Take a Photo with the Bean
The “bean” that everyone knows and loves, which is so identified with Chicago at this point, is a beautiful sculpture called “Cloud Gate.” This is really a stunning piece of art, and photos on the Internet can’t do it justice. Unfortunately, the area around the sculpture was off-limits during my visit due to construction, but it can’t be missed. The way it reflects the world back is somewhat dystopic but real at the same time.
Cloud Gate is located in Millennium Park, a public park that is part of the undeveloped piece of waterfront in Chicago.
There are at least nine public parks and beaches (yes, beaches!) in Chicago and you must walk through at least one.
The parks are peppered with art, accompanied by a wind that whips off the Lake. There is beautiful landscaping year-round and it is all set against a backdrop of stellar architecture.
- The Bean sculpture is called Cloud Gate and is visible from both inside the park and the main boulevard (Michigan).Â
- The sculpture is close to the Art Museum
Visit the Art Museum
If you have time to do one thing in Chicago, this is it. Bold statement. But trust me. Even if you don’t like art, there is something here for you.
The Art Institute of Chicago is right off Millennium Park, close to Cloud Gate, so its location is easy for tourists. Outside, it is unassuming. But inside, some of the most remarkable treasures ever given to the world of art are on display. While the entry fee can add up quickly for a family, I didn’t mind once I was inside and saw what they had collected, curated, and offered for public viewing.
Most of the famous masters have art here – from all eras. The galleries are huge, the entire museum meanders, and it is quite easy to get confused. It is also quite easy to get overwhelmed!
My recommendation: install the app, bring your headphones, and listen to the museum guides discuss the pieces that have numbers on them. And then, find one piece of art you’ve never heard of and study it. Get engrossed with it. Feel what it’s like to discover a painting for yourself.
- The Art Institute of Chicago is online at: www.artic.edu
- The Institute is very close to “the Bean” sculpture and Millennium Park.
- There are free gallery tours at 1:00 and 3:00 that last 45 minutes.
- Use the gallery app for both the map and the audio descriptions of certain pieces throughout the museum. This was so key for my enjoyment of the art!
Eat at Some Good Restaurants
Chicago is teeming with delicious restaurants. There are more Michelin-star restaurants in this city than I care to count up (see the full list here). It can, actually, be quite stressful to even figure out where to eat. There are also classic restaurants, many of which may not have elite stars but do have legacies and loyal fans.
I felt less pressure to pick where I was going to eat since the food tour provided me access to some of the food that is a “must” while in Chicago.
So how to decide where to eat in Chicago? Pick the area you are in and start with cuisine. Also, consider your budget. Some food is art and they charge a lot for the experience.
The Purple Pig is a Michelin-star restaurant right on the Magnificient Mile (more on that below). The food is expensive, so it’s a treat. But with tapas-style dining, it is possible to try a few of the creative approaches to cuisine on the menu.
Frontera Grill is a Michelin-star restaurant that is wonderfully affordable. This place is also famous. Rick Bayless has built a restaurant empire.
There is discussion about whether or not he appropriated a culture he isn’t a part of to profit from, but by all accounts (including the bartender I talked to who has worked with Rick Bayless for over 20 years) Bayless is a genuine person who works hard, treats people well, and, in short, isn’t a jerk. That’s good. Because I didn’t want to feel guilty about liking his food so much! I got the prix fixe lunch and have no regrets. It was incredibly well-priced and included a dessert.
I also decided to try a newcomer that is highly rated while in Chicago. The lobster ravioli was handmade and fresh.
- Want more restaurant recommendations? Check out The 38 Essential Restaurants in Chicago.
Go on an Architecture Boat Tour
Chicago is synonymous with architecture. Skyscrapers, mirrored windows, and unexpected shapes reach up above you no matter where you go. It is hard not to be amazed.
But I found taking a riverboat cruise where a docent explained the major buildings, the styles, the histories, and the impacts of the architecture around the city to be crucial to understanding what I was seeing.
There are a couple of different tour companies out there, but I chose the one that was recommended by acquaintances. I had a wonderful experience.
The guide had so much to say that it was near-constant chatter (no room for Q&A!) but he was passionate about where he lives and what we were seeing. It was infectious.Â
The tour time I was able to work into my schedule started just as the sun was going down. In some ways, that was a bit of a bummer as there were some details hard to make out in the dark. But in other ways, this was phenomenal. The Chicago skyline at night is breathtaking. It is neon and white, dark and warm, tall and flat, reflective and bold… I loved being able to see the city this way.
We were given free nonalcoholic drinks and alcohol was available for purchase. The boat was small, the crowd was small, and while it was winter and the deck was exposed, I never felt cold. It was a wonderful experience overall.
- I went with the Chicago River Boat Architecture Tour and I did purchase tickets in advance: architecturetourchicago.com.
- They usually don’t run the boats at night as it is hard to see the details of the buildings the tour guides talk about; however, the last tour of the day leaves just before sunset and returns in the dark, when the skyline is lit!
Have Afternoon Tea at Russian Tea Time
This was my JAM. (Get it? Because there’s jam… #badwordjokes)
At a place like Russian Tea Time, the influence of the different cultures in Chicago is so evident and so lovely.
When I lived in Europe, I came to love tea time. And this is an authentic tea. While some hotels in America put the idea of high tea into overdrive (and charge for it), Russian Tea Time was affordable, delicious, and a perfect fit for an afternoon break from walking to see all the sites.
- For more on Russian Tea Time, visit online at www.russianteatime.com.
- Russian Tea Time is located off the main boulevard (Michigan) near the Art Museum.
- If you want to do this right, go hungry and get the full-service tea.
Go Up a Tall Building
Heading up one of the tallest buildings in Chicago for an epic view (or experience – keep reading) is a must.
In Chicago, you have two choices: 1, the Willis Tower (formerly the Sears Tower) or 2, the John Hancock Building.
The Willis Tower is slightly taller and offers a glass ledge to walk out on for additional money.
The John Hancock Building is very convenient to other tourist attractions (off the Magnificent Mile) and here you can pay extra to “tilt” out over the city from the top of the building.Â
No matter which building you choose, you can’t go wrong but you must go to one!
I was surprised by how dizzying it was to be up so high. I’ve done some tall buildings before, so maybe it’s age or maybe it’s just feeling so exposed in these particular skyscrapers (a helicopter flew by below me), but it felt VERY HIGH.
It was on the observation deck of the John Hancock building that I could feel how Chicago was laid out – and how many people live here. It was from this view that I could appreciate the intersection of the water, the parks, and the massive downtown.
- The John Hancock Building is on the Magnificent Mile part of Michigan Ave and is very convenient for other excursions.Â
- Purchase tickets to go up the John Hancock building from this company: 360chicago.com. I did not get tickets in advance and did not have any issues. There is a bar on one side of the observation floor called Cloud Bar that has, of course, stunning views.
- John Hancock Building/360 Chicago has the TILT experience (and they recommend getting tickets in advance).
- The Willis Tower (formerly the Sears Tower) Skydeck, is online here: theskydeck.com
- The Wilis Tower offers the LEDGE experience. While tickets in advance are not required, there is usually a wait to get out on the platform.
Walk Around the City
I logged a lot of time just meandering around the city blocks. Every day, my FitBit was so proud of how many steps I had taken.
Despite its crime-ridden media reputation, I felt completely safe as a single, white woman walking the streets where tourists most often are, and even going a little further astray.
But walking these blocks helped me see new buildings from different angles, stumble on flower beds with mums spilling out, and to see where people who live in Chicago go to grocery shop or get dry cleaning done (assuming people still get clothes dry cleaned).
Although things that are lovely but slightly over-rated: Magnificent Mile.
The Magnificent Mile is a wide boulevard in Downtown Chicago that is lined by high-end shops on either side. It is a pleasant walk, full of landscaped flower beds, beautiful things to see, seasonal decorations, and some fun store windows. But, ultimately, it is just a city road and you are also going to get crowds, overpriced lattes, and a homeless population looking for help. The odds are, as well, that you are going to end up walking up and down this stretch of road to see anything anyhow (it is close to the Art Museum, where the John Hancock building is, and so forth). So enjoy it when you are on it, but don’t build an itinerary around this.
But I loved strolling the blocks in Chicago, hearing the L go rushing overhead, watching people scurrying, and seeing the way the buildings reflected off of each other.Â
QUICK TIPS ABOUT CHICAGO:
Hotels downtown are expensive! But staying close to the Magnificent Mile and Millennium Park definitely enhanced my experience. Everything was walkable!
Leave yourself lots of time to get to and from the airport – like, a LOT! It took me an hour and a half to get from the waterfront back to the airport and it was not rush hour.
The weather changes quickly and they aren’t kidding when they call it the windy city. Bring layers!
BONUS: If You Have More Time, if Weather Allows
See an improv comedy show at Second City. Â
Catch some live jazz music.
Spend some time on Navy Pier.
Visit Wrigley Field – take a tour or see a game!
Visit the Field Museum.
Whatever you decide to do in Chicago, prepare to be impressed! It is a large city, so your visit will likely be a whirlwind of activity, culture, and humanity. But your visit can also be one that can open your mind and your heart. Enjoy!