Robert Paulson


Senior DevOps Engineer at Orca, LLC

you're not your job you're not how much money you have you're not the car you drive you're not the contents of your wallet you're not the opinions of your company and neither is this site

3 October 2020


by Robert Paulson

Chicago is one of my favourite cities in the world. When a good friend went to visit Chicago, I generated this list of places I usually end up in every time I visit.


I recommend walking around a lot - we crossed the entire city in maybe 45 minutes on foot, and from the bean to the surgery museum it’s like thirty minutes walking. With kids things are different, of course.

I recommend walking around the bridges and along the river going to the south part of the town - some nice old huge buildings there, like the Opera house.

The pier is a waste of time - very commercial, nothing good there. However, walking around south of it on the rim of the park (the coastline) is cool, plenty of boats and stuff.

Metro is easy and reliable. Crazies are less crazy than the LA crazies.

Lagunitas Brewing Company Chicago

Never been there but it’s great beer.

Skydeck Chicago

Good view of the city I guess. Costs some money, don’t pay them anything past admission, try to go on a weekday because it does get crowded.

Wait no I’ve never gone here - I’ve been to the other highrise that’s above the Cheesecake restaurant (which actually has decent steak). Doesn’t matter where you go to see the skyline.

Good for family trip.

McCormick Tribune Plaza

Where the bean is. Just walk around the park and stuff while drinking beer. Go south, there’s a long bridge that’s kinda cool - leads you to the museum of art or something. Haven’t been to the actual museum, no reason it wouldn’t be great but is usually crowded.

Good for family trip.

The Picasso

Just a famous thing next to a lot of metro lines.

Good for family trip - while walking around the city, I presume.

Pierogi Heaven

Never been here, wanted to go. High rated food place.

Probably good for family trip.

Andy’s Jazz Club & Restaurant

Great Jazz place, not small or divey but good.

Probably not the best for the whole family and kids and shit.

Lou Malnati’s Pizzeria

Best pizza you’ll ever have. Did research, is the best deep dish pizza in the city, and therefore the world.

Definitely good for taking the whole family here.

Blue Chicago

Very good jazz bar - though they usually play blues I think. Very good, divey. Go on a Thursday if you can to see the band Anna and I saw last time we were there.

Might be okay to go with kids here.

Gilt Bar

Best manhattan I’ve ever had. Is not quiet nor divey.

Probably less good to go here with kids.

Timothy O’Toole’s Pub Chicago

Simple pub food beer place. Nothing special but open late, unlike many other places.

Probably good for family trip.

Quartino Ristorante

Very cheap italian food with cheap but good wine list - love this place.

Great for the whole family thing.

Al’s Beef

Some kind of legendary well-known beef sandwich place. Very good, fast-foody. Place is small so best case scenario is taking it to go to the nearest park. We took it to a tiny church courtyard where we had beer. Illegally, of course.

Probably okay with kids - but more likely you’ll postmates it to you or something.

International Museum of Surgical Science

Fantastic museum of surgery - highly recommend walking to it from the city on the beach. Make sure you check when it’s open.

Directly north of it is a cool park that I also recommend for aimless walking.

Directly west and south-west of it are older suburbs with cool houses all over. Recommend aimless walking here as well.

Kids would love this place.

The Green Mill

Legendary Jazz bar. Highly recommend you make your way out there - best case is by metro, it’s easily accessible from there.

Probably not best for kids - but if you snag a booth anything is possible.

Eataly Chicago

Very very good Italian food, is more expensive. The building houses several restaurants - one for desserts, some wine tastings around, some Italian food around. Eataly is the one restaurant we went there to, I recommend it.

Good for kids and exploring that whole building and shit. Make a reservation.