I have been in Chicago numerous times through the years, all on the job and once on vacation — 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 January, 2026, while on vacation, and before that February, 2023, and numerous other times before that.

So this is what I’ve learned as good things to do in Chicago and surrounding area:

1. Ride the “El” Train

Riding Chicago’s El train — El for Elevated since it is almost entirely above ground– is a must do. You can buy a day pass, or put money on pass and ride — a base pass cost $5 at current writing and then you would put at least $5 additional dollars on it for 2 trips (coming and going) — each trip is $2.50 at current writing.

Take the Red line from down town south toward Dan Ryan and cruise thru the inner part of the city above ground like Spiderman.

Best Way Into Downtown from Airport Is the “El”

And if you are at the airport — the cheapest and just about fastest way to get into downtown, if you are not renting a car, is to take the metro.

Just follow the signs to the Chicago Transit Authority (CTA) trains — informally known as the “El” 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).

Most of the trip from the airport to downtown is elevated (from airport to Wicker Park) so you can look out the window and see Chicago neighborhoods as you travel in.

2. Walk the Neighborhoods

If you have a few hours or more to spare in Chicago — hop on the elevated subway and take a ride to one of Chicago’s neighborhoods.

Wicker Park

One one of my trips to Chicago, I was at the airport with 5 or 6 hours to spare, and jumped on the L train. I was on the Blue line headed 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. I had hit paydirt — because Wicker Park is a famous neighborhood — known for “for its hip local culture, art scene, nightlife, and diverse food and shopping options — and also recognized for its historic architecture, independent boutiques, and trendy restaurants.”

There is a wonderful donut shop called Stan’s in Chicago, which has big, thick, tasty donuts — absolutely amazing. The Stan’s at Wicker Park is their original location. 

The main drag of Wicker Park is North Milwaukee Avenue. Beautiful shops there. While there I stopped in and 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, under the elevated train tracks.

Visit Myopic Books in Wicker Park

There is a bookstore on North Milwaukee Avenue named Myopic Books — a good old fashioned bookstore featuring tons of new and used books in nooks and crannies on multiple levels.

Myopic Books is similar in tenor to Strands Bookstore in NYC.

Lincoln Park

Lincoln Park is similar to Wicker Park — but even more prestigious in terms of the well-to-do mansions that litter its side streets. DePaul University is headquartered in Lincoln Park — which makes the area a College Town within the big city.

You can walk from Wicker Park, over the Chicago River, to Lincoln Park — it is about a 2-mile walk. Or you can take the Red Line train directly into Lincoln Park — getting off at the Fullerton Station — and walk around. To the immediate West of the Fullerton Station is DePaul University’s main campus; to the East lies the heart of Lincoln Park, including the park itself.

Visit the (Free) Lincoln Park Zoo — See the Lions

Lincoln Park itself was named after Abraham Lincoln — there is a statue of him sitting on a bench at the front of the park. There are also statues of Ben Franklin and of General Ulysses S. Grant on his horse inside the park.

Lincoln Park offers a free zoo — which has a lion family, and a large reptile collection amongst other things.

You can walk thru the park, and down back into the city. Lincoln Park is 2.5 miles from Trump Tower and downtown. It is a wonderful walk.

Downtown — Visit Trump Tower

If you are walking downtown, you will encounter the magnificent Trump International Hotel & Tower — which dominates downtown. It is a gorgeous tower — rising 1,388 feet — currently the 6th tallest building in the United States. It was the 3rd tallest building when it was completed in 2008, and was originally designed to become the world’s tallest building but Trump pared down the design after the September 11, 2001 attacks on the World Trade Center.

The Trump Tower sits right on the Chicago River at a key junction of the River Walk — and the huge TRUMP lettering speaks one million words of power and elegance.

You can walk into the lobby and then head upstairs to the bar. When I was there with family in January, 2026, there happened to be a huge NFL wild card playoff game going on between the Chicago Bears and Green Bay Packers — which had a wild ending (Chicago scoring 2 touchdowns in the final minutes to turn a loss into a win).

We watched a part of the game in the glamorous bar area.

Miracle Mile

You can also walk around downtown Chicago, and take in “Miracle Mile” — which is Michigan Avenue with all of its fancy shops. Michigan Avenue isn’t the miracle it once was, but is still a fun, vibrant walk.

Touch the Bean in Millennium Park Downtown

The Bean, officially called Cloud Gate, is a giant, reflective stainless-steel sculpture in Millennium Park downtown. It has become a must to go up and touch it and photograph yourself off of its mirror-like exterior. It was designed by Anish Kapoor.

If you walk underneath the beam, you get an infinite mirror effect. The Bean may or may not resemble a woman’s womb?

3. Walk “River Walk” & View the Architecture

Walking downtown the first thing that hits you about Chicago besides the skyscrapers is the Chicago River that cuts right through town. And depending on the time of year the Wind. There are various websites that offer advice on taking river boat tours — such as a Chicago Architecture Cruise which I’ve never taken but would love to.

But Chicago has created a system of walkways to allow you to walk and run around the river. The river branches off in several places — it has a North, South, and Main branch — and then there are several man-made canals.

If you are downtown, you can walk to the river and follow the “River Walk” signs.

You can walk to the Navy Pier, and catch the “River Walk” from there — and walk around the front of Chicago to Millenium Park and Michigan Avenue, observing the incredible Chicago skyline as you go. But stay in your walk lane and watch out for bicycles ripping by. You can also run the path — lots of runners will run by.

4. Watch Live Blues

Chicago is known for its Blues venues. For a good time — possibly great time — try to spend a night catching live blues at one of Chicago’s Blues venues.

Note that you must be 21 years old to attend a Blues Bar. One place that allows under 21 is Kingston Mines — which allows 12 and over if accompanied by parent. Rosa’s Lounge allows people under 21 if they are accompanied by parent and you call ahead. Other places are stricter.

The most popular ones are:

• Kingston Mines — Has 2 stages; is on the North Side; 2548 N Halsted
• Rosa’s Lounge — NW Side by Logan Square; 3420 W. Armitage
• Buddy Guy’s Legends — BOOK IN ADVANCE — SELLS OUT — South Loop; 700 S Wabash
• Mom’s Place — River North; 650 N. Dearborn
• Water Hole — Has a Blues Jam Wednesday Nights — University Village; 1400 S. Western Ave.
• Taylor Street Tap — Little Italy; 1358 W. Taylor St
• Reggie’s Music Joint — South Side; 2105 S. State
• Nick’s Beer Garden — in Wicker Park; 1516 N. Milwaukee Ave

Rosa’s Lounge

One of the better ones is Rosa’s Lounge. 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.

First time I was at Rosa’s, as 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.

5. Take in a Game at Wrigley Field

I was in Chicago in April one time and went to Wrigley Field for an evening. 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.

Wrigley Field is of course one of the oldest stadiums in Major League Baseball, having been built in 1914. It is second oldest to Fenway Park, which as built in 1912. Wrigley Field was the last stadium to install electric lights — 30 years after every other stadium brought them in. Up until 1988, there were no night games at Wrigley, and games were suspended to the next day if it got dark out.

Wrigley Field also has a very famous, hand-operated scoreboard built in 1937.

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.

You want to try a Smokie — a smoked beef sausage.

Other food featured:

• Smoked Brisket Sandwich by Lillie’s Q
• A Pork Chop Sandwich served with grilled onions and mustard on a toasted bun
• Garrett Popcorn was very popular, and
• Of course hot dogs, etc.

6. Catch 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.

7. Catch a Bulls Game

I have never been to a Bulls game. I’m a Knicks fan.

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.

8. 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. The boats all take off from the Navy Pier, at the front of Chicago on Lake Michigan. You can walk to the Navy Pier from downtown or take an Uber.

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.

If you have business in North Chicago and are staying there — like I was in 2018 — then you might 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.

What to Eat

Chicago is known for its Deep Dish Pizza. There are numerous recommended restaurants for it:

• Giordano’s
• Geno’s
• Lou Malnati’s
• My Pi
• Pequod’s
• Bartoli’s
• Beatrix Market
• Labriola

Geno’s for Deep Dish Pizza

On one trip to Chicago, we at the Deep Dish pizza at Geno’s — which at time of writing had highest ranking of all the above restaurants with a 4.7 out of 5.

Geno’s is downtown. The restaurant allows you to write on its walls, and provides magic markers for you to do so. So people have written all over it — on its ceilings, walls, etc. The pizza was thick and the sauce was amazing.

Starbucks Reserve for an Alcoholic Drink

Starbucks has opened a 4-story modern glass building downtown on Michigan Avenue — at the start of the Miracle Mile — that offers alcoholic versions of its drinks on the 4th floor, unique drink experiences on its 3rd floor, a normal full-bodied Starbucks experience on its 2nd floor (with amazing deserts), and grab-and-go Starbucks on its bottom floor.

We stopped in and tried the Espresso Martini — which was $20 a drink — but it was amazingly well worth it — an AMAZING drink and VERY STIFF with premium alcohol. One of the best drinks I have ever had. It is well placed and worthy of Miracle Mile.

Where to Stay

I’ve stayed at numerous places in Chicago — both downtown and out by the airport. On the last stay, the family (including 2 dogs) stayed at in a suite at Homewood Suites in downtown Chicago on East Grand Street. It was a terrific room on the 17th floor at a reasonable price ($150 to $190 a night), and had terrific views — we had a direct view of the Sears Tower.

The Homewood Suites’ hotel lobby is on the 6th floor and has amazing views of the Trump Tower and other downtown buildings. Note this is the Homewood Suites in downtown (E Grand St) — there are 3 Homewood Suites in Chicago.

Trump International Hotel

You could of course stay at the Trump International Hotel and Tower. We toyed with this — it was $490 a night when we were in Chicago in January 2026, vs the $200 a night we were paying at the Homewood Suites. We would have done it for the last night, but were so comfortable with our 2 dogs at the Homewood Suites with a room on the 17th floor and wonderful views. Next time.

Where to Park If You are Staying Downtown — Will Cost $$

Beware if you choose to stay downtown: if you have a car, you will need to pay to park the car, which will cost $40 to $72 or more a night — depending on if you self park or use the valet.

The valet at Homewood Suites where I stayed in January 2026 charged $72 for a valet. I didn’t choose this but if I did, it would enable me to use the car when I wanted for the one price.

For self parking, it is recommended to use the app SpotHero to park — it will provide a map that shows cheapest places to park. Important Note: if you park somewhere via SpotHero, you can’t go in and out of the parking lot — once you park in a lot, you have to keep your car there for the entirety of the time period you’ve rented — if you leave — then your spot is gone.