I’ve visited Chicago several times in the past and for some reason never loved it. So when a college friend invited us to a wedding in Chicago, we decided to live there a month to investigate why I didn’t love it in the past, and see if I could change my opinion.
For context, I had a similar feeling about NYC before I moved there and then found things I absolutely love about it. So let’s see if my experiment was a success!
Walkability
Chicago is wonderfully walkable! There were sidewalks absolutely everywhere with walk signs and crosswalks. However, I saw a lot of people run red lights – more than I have anywhere in recent memory.
I was in several ride shares that blew through red lights and stop signs. Generally, traffic laws seemed like a mere suggestion. But like any major city, I always assume everyone driving is drunk AND watching a movie on their phone and I walk accordingly.
Crime
Since living in NYC, I like to compare crime data to that city when evaluating a new location. And until this month, NYC had always had more crime than the city I was moving to. Well, now Chicago has taken that crown.
However to put this in context, by population, Chicago is ‘only’ #42 by crime rate on the list of 100 most populous US cities. NYC is #67 and Seattle is #97.
Unfortunately, I had these numbers in mind when we had an ‘interesting’ introduction to our new home in Chicago. We rolled up and while I was trying to get us into our Airbnb, we heard a crash and I later saw someone driving under the influence onto our street’s sidewalk.
We were then able to get into our home and saw that this same car had parked right behind it. A few minutes later, the police were there, lights flashing into our windows. Welcome to the neighborhood, I guess?
Now, this is far from the worst ways we’ve been introduced to a new neighborhood (see my second year of NYC living here), but it wasn’t the best intro to our new home for the month. However, after that ‘exciting’ first encounter, things calmed down.
Nevertheless, I have found myself reverting back to more NYC style behavior while living here. I don’t run alone or walk alone at night. I’m also aware of my surroundings in the way I always am when in bigger cities or unfamiliar places.
Transit
Chicago has a large transit system that includes a subway called the “L,” which stands for “elevated train” because it’s mostly above ground. There were also buses going by constantly so they seem to have those two options covered.
However, while in the city, I only walked or took ride shares except once like the bougie bitch I’m becoming π . When I was looking into using public transit, it seems like you can buy a transit pass (or “Ventra” card) at many retail stores, add money to it online and then hop on a train or bus. Strangely all the stations I went to did not have kiosks where you can buy tickets like NYC. However, if you can get a ticket it costs $2.50 for a ride on the train or $5 for a day pass.
If you do end up mostly taking cars around like I did, just a heads up that Chicago is currently ranked as the US city with the worst traffic π . There always seemed to be bumper to bumper traffic as well as constructions and detours galore, which happens in the summer when the weather is better. Definitely plan accordingly π .
So allow for extra time if you need to be somewhere at a specific time. Also note that I did have trouble getting cars to go from downtown to farther out of the city. I was always able to do it, but at times it would take multiple tries (and increased prices π ).
Inclusivity
Chicago is the home of the first recognized LGBTQ+ rights organization in the US! Between that fact and me being in the city during June (Pride Month), there were queer flags everywhere – and I loved it π . Interestingly, Chicago also has the 3rd-largest LGBTQ+ population in the United States with an estimated 7.5% of the adult population or 146,000 Chicagoans!
So that made me feel more comfortable around the city, but something else that did is the abundance of people of color. According to US 2019 census estimates, Chicago’s largest racial or ethnic group is White with 32.8% of the population, Blacks with 30.1% and the Hispanic population with 29.0% of the population. That is a surprisingly pretty even split!
However, Chicago is still quite separated along racial lines, which the below map helped me understand. To help understand it, here’s the KEY: Red = White, Blue = Black, Yellow = Hispanic, Green = Asian.
Nature
Now this I didn’t realize based on my previous visits to Chicago: there’s nature almost everywhere π . Lake Michigan being right next to the city is a large part of that. As a result, there are over 200 beaches in Chicago as well as running and biking paths that go all along the coast, including to and through downtown.
There are also an abundance of parks around the city, which allowed me to do so much birdwatching! Even in a park in the middle of the city, I saw a wild amount of my feathered friends. I’m going to list the types of birds I saw in my monthly recap like always, but I was surprised by the amount I could see for a metropolis.
Another great thing about Chicago is that there are laws against building on the waterfront so it is public space that everyone can enjoy along Lake Michigan, and I think that’s awesome. Similarly, there is a Riverwalk that surrounds the Chicago River that goes through downtown, which is more public space.
Climate
I was impressed with Chicago’s June climate. It was mostly sunny and even when my weather app claimed it was 80F+ degrees, it felt cool to me. Though maybe that was the wind coming off the Lake π . Overall, here is what the climate in Chicago looks like (based on 2015 data so add a few degrees to each estimate):
Food
I was told by locals that Chicago has a lot of unique food, such as Chicago hot dogs, deep dish pizza and Italian beef sandwiches. While I enjoyed trying those foods, the ones I actually enjoyed most were my samplings of pasta, mediterranean and Chinese food. Random π , but delicious is delicious so I’ll take it!
Cost
I like to base estimates on solid facts and that’s why I began my retirement calculations by assuming I would continue spending the same amount that I did during my awesome HCOL life in Seattle, which cost $18,000 a year. I then added 11% on top of that amount just in case, to come to a round $20,000 for my annual retirement budget.
So how did Chicago measure up? It’s one of the top 3 biggest cities in the US and I expected it to be quite expensive accordingly. So, is it?
Kind of π . Chicago is fairly cheaper than NYC, which I wasn’t expecting given all this city has to offer.
LodgingΒ
Cost: $1,644.54/month per person
We got a 2 bedroom apartment without the intention to use the second bedroom (we just liked this Airbnb best), but having it allowed us to invite my Mom to visit for a week and friends to visit over weekends, which was awesome!
Interestingly, this place could be billed as a 3 bedroom because there were 3, but the 3rd was empty so we turned it into a walk-in closet to go alongside the 5 other closets we had. Such luxury π . In addition to amazing storage space, this place had an in-unit washer/dryer, 2 TVs (and one was enormous) with access to every streaming service imaginable, a backyard and a patio. I’ll be posting lots of pics of our stay on Insta next week per usual π .
Food
Grocery Cost: $68.42/month
Yeeeah I didn’t eat that many groceries this month π . There were too many yummy new restaurants to try! However, when I did pop by a grocery store I had new experiences, such as learning that the local Jewel-Osco is a part of Safeway (and if you go in it looks just like it). My Safeway card number even worked there for some nice discounts π .
Eating Out Cost: $339.15/month
This is unsurprising and I have no regrets!
Transit
Cost: $138.59/monthΒ
As I mentioned, I was bougie this month and took ride shares everywhere – including far out of the city for a wedding. If I had taken public transit while in the city this would have been a lot lower, but it’s good to know how much a new bougie life would cost in this category.
Entertainment
Cost: $7.28/month
This isn’t wild because so much to do in Chicago is free! Parks, the beach, gardens, art installations and even summer concerts. There’s no lack of entertainment in every direction. This cost is actually from me seeing a matinee of Across The Spiderverse. I love weekday matinees in almost empty theaters π .
Conclusion
After a month of exploring, I did find many things I enjoyed about Chicago, specifically the weather (we were there during late May/early June it was sunny and 70s most of the time). I also enjoyed the walkability, which I’ll get into below. Chicago is the 3rd most populous city in USA after NYC and LA so it sits right after my previous home of NYC for giant, walkable cities.
There is also a wild amount of gorgeous water in Chicago, from Lake Michigan with its turquoise waters to the Chicago River that goes through downtown and is surrounded by river walks. The architecture was also a very interesting time capsule to explore the city’s history.
I now have a new appreciation for the beauty of the city, specifically its river, beaches and architecture. And if I return, I still have a wild amount of food recommendations I need to tackle! Until next time.
What’s your favorite large city?
If you’re interested in my other Slow Travel Reviews, they’re all here:
- Slow Travel Review: Portland, Maine, USA – The Land Of Deliciousness
- Slow Travel Review: Catskill, New York, USA β The Land Of Mountains
- Slow Travel Review: Santa Fe, New Mexico, USA β The Land Of Chili Peppers
- Slow Travel Review: Decatur, Georgia, USA β The Land Of Flowers And Food
- Slow Travel Review: Phuket, Thailand β The Land Of Sea & Food
- Slow Travel Review: MΓ©rida, MΓ©xico β The Land Of Color & Nature
- Slow Travel Review: Seattle, WA, USA – The Land Of Flowers, Sea And Mountains
- Slow Travel Review: Sacramento, CA – The Land Of Flowers & Sunshine
Very cool – a thorough review!
My sole visit to Chicago was for a conference that was, unfortunately, in November. Not a great time to visit Chicago, though I admit it was pretty with the snow. It was just too cold to go outside to to anything.
Maybe that planned it that way, so people wouldn’t skip the conference π
Whoops! Should be:
“too cold outside to *do* anything.”
Thank you! And yeah winters here are rough – I’ve been here a few times during that time too. And lol I bet they did plan it that way π .
My favorite memories of Chicago are the Field Museum (Sue the T-rex!), the Willis Tower observatory (which has slightly better views than the Sears Tower), and the Goose Island brewpub, which had some of the best food-beer pairings I’ve ever tasted.
I wouldn’t recommend the weather for most of the year, though. π
Willis Tower = Sears Tower
They are the same building
Very cool! I haven’t been to Goose Island yet, but it’s on my list for my return visit.
Sounds like time well spent π
The things I enjoyed most about Chicago
– the walkability
– its architecture (including learning more about it on the Chicago River aboard the First Lady and in the Architecture Center)
– the American Writers Museum which is very interactive
– the views from Willis Tower and from the former Hancock Tower
Nice! I haven’t heard of the American Writers Museum and am adding it to my list.
For some reason, the American Writer’s museum is low profile and rather difficult to find- and I’ve lived here 25 years.
I used to live there when I was very little and remember my mom hoarding (ok saving up to reuse) plastic bags from Jewel!
I really don’t understand how your eating out costs were just $340! I am in a the desert southwest and lower COL than Chicago. I took a friend out the other day for breakfast at some run-of-the-mill breakfast place and the bill was about $32 per person for an omelette, coffee and juice, including tip. I don’t even go out for dinner ever since I was slapped with a $50 bill for ordinary pub-fare a few months ago – a few beers, appetizer, and a bacon cheeseburger.
Even at $20 a meal, you’d only be able to get 15-20 meals for the whole month eating out! What’s your secret?
They do give a lot of plastic bags lol. We were surprised because we bring our own bags everywhere and expect to be charged for them. No huge secret here unfortunately. We found a few places that were well priced that we absolutely loved and gave huge takeout portions, which gave us a ridiculous amount of leftovers. I’m posting about those places on my Insta in a few days if specific examples help!
It’s been my experience that COL estimates are just ridiculously dumb. So skewered toward house prices. I’m from a tiny town in the midwest with cheap houses, but the cost of food, electricity, travel, dining out, internet and everything is much higher. Some crappy chain restaurant (generally all they have) costs twice as much as a delicious mom and pop thai place. My electric bill there in 1999 was higher there than my bill here has ever been in 2023. Buying groceries for my parents was ridiculous. Corn o the cob cheaper and the little mart across the street than the grocery store back there- which was in the middle of a cornfield.
Airline ticket for my friend from our hometown to NYC- 1100. Chicago to NYC- 212.
Ugh, people really need to look at what the life THEY WANT TO LEAD costs in these places. Sorry. Rant over.
My best memory of Chicago is entering the subway station at O’Hare one busy winter evening for that loooooong ride downtown to an interview, and a woman passerby slaps a ticket into my hand and goes on her way without a word. Thank you lady wherever you are!!
Oh wow – that’s so kind!
The last time I was in Chicago was in February and it snowed 16″. Luckily it was for a conference and there was a shuttle, driven by someone who knew what they were doing, to get back and forth to the convention center. But it wasn’t really walkable. I live in Washington, DC. It is a wonderful city to explore with many free things to do as well as a wide diversity of food options. I would not recommend visiting in the summer. The humidity is unbearable. October is lovely though. As is May.
Oh my! Well I’m glad the conference planned ahead like that. That sounds rough. I have been in DC in the summer and it was a bit of a challenge π .
Glad to see you enjoyed the Chicagoland area. As a transplanted resident (55 years in the NYC/NJ area and 10 years here in the “Chicagoland Area” near Oak Park), I would like to make a couple of suggestions, if you haven’t done them already: Check out the Jazz/Blues/Cabaret music scene all around the city; slip outside the city for some of the more…interesting… nearby suburbs like Oak Park/River Forest (heavy yuppie/buppie/guppie…and townie… influences in a diverse population), Evanston (right next to Chicago…); if you do use mass transit, consider the Metra lines instead of Chicago Transit trains because they are more like express lines to many outside areas.
Just a couple of things to consider…among many. Glad you enjoyed our area!
David S.
Thanks so much for the suggestions! I’ve added them to my list for when I return.