I have been in Chicago numerous times through the years, all on the job — and always try to ignorantly plow forth and explore the town when work is done.
I spent one week in North Chicago a few years ago, at the Naval Station Great Lakes, and have visited customers numerous times in downtown Chicago, including Bank of America and others.
The most recent visit was in February, 2023.
So this is what I’ve learned as good things to do in Chicago and surrounding area:
1. Take the Train from the Airport
Cheapest and just about fastest way to get into downtown Chicago from the airport, if you are not renting a car, is to take the subway.
Just follow the signs to the Chicago Transit Authority (CTA) trains — informally known as the “L Train” (for eLevated trains) — Chicago’s extensive subway system. You can buy a 1-day pass for $7 and then take it into downtown. It will take you just about the same time — 45 minutes — as taking a taxi ($65) or Uber or Lyft ($40).
On top of the big cost savings, the trains are all elevated (thus the name) so you can look out the window and see Chicago neighborhoods as you travel in.
2. Neighborhoods
With 7 hours to spare at the airport on one of my trips to Chicago, I hoped on the subway and took a ride toward downtown. I examined a Chicago map on my cell phone and picked a train station where I thought there would be a lot of activity, based on the stores in the neighborhood. I jumped off at a stop called Damen, at a place called Wicker Park.
I walked down into the streets and found the Wicker Park area to be a terrific area — very trendy with lots of shops in old Chicago storefronts.
There is a wonderful donut shop called Stan’s, which has big, thick, tasty looking donuts. I was tempted to buy some but didn’t. I found out later that Stan’s Donuts has many locations in the Chicago. This looked like a good one — maybe their original spot? 
I walked down a main drag — North Milwaukee Avenue — and browsed a couple of shops. Had an espresso at a Starbucks. It is a nice area to walk and feel the vibe of Chicago.
Behind the main drag — North Milwaukee Avenue — there is a parallel street where all the garbage pickups are done. This offered a more interesting walk. I bought a cigar in a shop on North Milwaukee and smoked it back here.
Then I stopped into Myopic Books — a good old fashioned bookstore featuring tons of new and used books in nooks and crannies on multiple levels.
After browsing for a bit, and reading thru some books, I bought a t-shirt and Myopic Books button — which is that of an all-seeing eye.
Nice bookstore.
3. Rosa’s Lounge for Live Blues
On a prior trip to Chicago, when I worked at the Naval Station Great Lakes for a week — I set out one night to hear some good ole Chicago Blues. I searched online and determined to try out Rosa’s Lounge. I was not disappointed.
It’s one of those old Blues bars wherein different artists come walking in as the evening progresses, get up on stage, and perform tremendously — act after act. When I was walking into the place, I noticed a young black woman with guitar on her back walking towards the place as well.
I went inside, ordered a drink, sat at a table by myself and listened to the group performing. She entered — and sat down. Thirty minutes later she was on stage — tremendous singer and accompanying herself on guitar. That is the kind of place it is.
As I sat there you could tell other artists were coming in and sitting down, waiting for their turn — which culminated in a hoot-en-any near about 11pm — with a group of about 7 blues players performing — wonderful stuff the kind of place you don’t want to leave.
But with work the next morning I had to — and left around midnight with the place rocking. It was a Wednesday night.
4. Wrigley Field
On that same trip to Naval Station Great Lakes, I went to Wrigley Field one night. It was in April and I froze my ass off. But had a fun time at Wrigley.
Wrigley is located north of downtown, in the Lake View section of Chicago — near the lake actually. I was able to park my rental car about 10 blocks from the stadium on the street for no cost. I think I parked on Waveland Avenue.
As a Yankee fan, familiar with the new and old Yankee Stadium (as well as the Mets’ Citifield and Shea Stadium, and Fenway, amongst other stadiums) — Wrigley was a throw back in time from a food standpoint. They don’t have the complex offerings of modern parks, but what they do offer is very interesting, tasty and different.
Food featured:
- Smoked Brisket Sandwich by Lillie’s Q
- A Pork Chop Sandwich served with grilled onions and mustard on a toasted bun
- Sausages, and
- Garrett Popcorn was very popular, and
- Of course hot dogs, etc.
5. Bulls Game
I have never been to a Bulls game. I’m a Knicks fan. In my opinion the NBA under David Stern made sure Jordan had the wind at his back in terms of referee calls on the offensive and defensive ends, and made a superstar into Superman.
But many Europeans want to take in a Bulls game — for example a few that I traveled with once on a trip to Chicago. So that’s something you might want to do. They play their games at the United Center, which is just West of downtown Chicago.
6. Take a Sunset Cruise by the Waterfront
I spent a night on a party boat on the Waterfront once a long time ago — back in the early 2000’s — like a dream and vague memory. What was nice about it is that you are in the water in Lake Michigan viewing the Chicago skyline — which you can’t do at a lakeside restaurant on shore.
There are various websites that offer advice on Sunset Cruises that you can book for about $40 a night per person.
There are also various websites that provide good advice on restaurants to eat at on the Chicago Waterfront. Some are:
7. Experience Downtown, the Canal, the Wind
Walking downtown the first thing that hits you about Chicago are the canals. And depending on the time of year the Wind. There are various websites that offer advice on taking canal boat tours — such as a Chicago Architecture Cruise which I’ve never taken but would love to.
8. See a White Sox Game
Don’t forget the White Sox. Comisky Park is no longer — the White Sox now play at a place called Guaranteed Rate Field. It is located where Comisky was — on the South side of Chicago — literally very much south of downtown Chicago, whereas Wrigley Field is very much North of downtown. The two stadiums are about 1o miles from each other.
9. North Chicago by Car
If you rent a car, you can drive along Lake Michigan and pick some streets at random to drive down to see the lake — Lake Michigan.
More formally, you can drive to places like the Illinois State Park and Nature Preserve, which is a big park on the waterfront that includes the Waukegan Municipal Beach that features a sandy beach. I’ve not been there.
I did drive north of Northern Chicago to Kenosha, Wisconsin — a 30-minute drive from Northern Chicago, which itself is a 30-minute drive from downtown Chicago. Kenosha features the closest Texas Roadhouse in the area.
See my review of a place to stay in North Chicago here.
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