Cubs game at wrigley, stop at one of the several pincades/barcades. Can still do wrigley tours if cubs are out of town. Portillos to eat. Architectual tour is awesome you will enjoy. Hancock building or sears/willis tower. I like hancock slightly better, closer to the lake.

Go to HQ, grab a burger and play free pinball

I really enjoy the Science and Industry museum. The Uboat is just incredible to see.

Also, Stern was very cool about letting me do a tour. I toured back in Jan of this year.

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Taking my kids to the Windy City for their first time in July, it's my favorite big city in the US. I am trying to put together a Ferris Bueler tour for them, but can't find anyone to rent me a Ferrari for the day.

Pizza - I'll bet you a dollar you will convert to Chicago style pizza after 1 weekend there. Only New Yorkers like NY pizza after a real Chicago experience. - flame suit on! We always try to hit one of these whenever we are there. Honestly there are dozens of neighborhood shops that are just as good, but try these to find which style you like best.
Ginos East
Giridano's
Lou Malnati's
Pequod's

Fine dining -
Chicago hasn't been the same since Charlie Trotter died and his restaurants closed.

But my Second favorite chef is Rick Bayless. Visit Frontera Grill or Topolobampo, especially if you like tequila and mezcal, the selections are endless.

Lawry's is a classic if you like beef.

First, you are on the right track but I don't know how much time you will be in town. Navy Pier is cool and there are boat rides on Lake Michigan. Deep dish pizza was started by Pizzeria Uno & Due I like them both. If you enjoy horse racing you can take the train dt to Arlington Park racetrack, very enjoyable.

Also by Lincoln Park and the Zoo on Clark St. is Chicago Pizza and Oven Grinders (upside down pizza) and almost across the street is where the St Valentine's Day massacre happened. We have a nice walkway following the Chicago River. Have fun.

If you are staying for more than a day, consider doing a private and free walking tour with a Chicago Greeter. We've done this a couple times and it's been really good. There are a number of neighborhoods you can choose to cover.

http://chicagogreeter.com/

The Art Institute, Millennium Park, Seadog Turbo Boats, Magnificent Mile Shopping, Brookfield Zoo, Segway tours. All are great!

Everything at Portillos is great I would try at least two things trya small size/ regular beef and combine it with either a chicago style hot dog or a cheeseburger. Cheese fries are great 2. Only thing I didn't love there is the fish.

Galloping Ghost Arcade - Largest arcade in the world !!!! Doc the owner is an encyclopedia of arcade knowledge from the games themselves to the people and companies who make them. They have regular visits by well known designers and industry leaders. Plus Doc and his staff are just awesome folks who love to chat and have a good time.

Thanks
Blake

Good news is that you cannot smoke in restaurants, bars, etc. so you should be safe at Spin Chicago or any other establishment! A couple of other places to consider include breweries (Revolution, Half Acre, Lagunitas and about two dozen others), the barcades (Emporium and Headquarters) and how about Southport Lanes? A bowling alley might not the best place for your pregnant wife BUT it's one of the few (only?) places with manual pinsetters...if you see legs, DON'T bowl!

Galloping Ghost looks to be a bit of a haul on CTA/Metra from the North Side (Rogers Park) where I'll be moving soon, but sounds like it's worth it. Same with Stern. Both the pinball player and the urban/street photographer and architecture fan in me are going to be happy.

There are a LOT of pinball locations that I see on the maps. Particularly from the Loop area and north. Wouldn't expect anything less from the city where most of these games were made. Already making notes of where to play certain pins I haven't seen in a long time.

there is a great walkthrough vid on youtube from Johns Arcade. Doc Mack takes John through the entire place giving commentary on some of the rarest prototype and unreleased titles in the industry. Super cool if you love vids and the history of the coin op industry.

Thanks
Blake

A bit of a downer to see they only show three pins, but they look like they're in top shape, and Creech/FH/TZ on free play is nothing to cry about whatsoever. Thanks for sharing.

I'm told it's been hot/humid Gulf Coast-style in Chicago this weekend. Even adults are running through the splash parks and whatnot. OP is in Lake Charles, so you know how to handle that.

Love Portillos! I’m not a purist, I get my Aujus on side so I can dip it. That way bread doesn’t fall apart too early. Otherwise sandwich gets dunked and wrapped. Galloping ghost is awesome, if arcades are your thing, I love them too, but many on pinside don’t. Michigan ave is a day with sears tower, and boat rides down river. If you get a rental car there’s a big car “museum” out in Volo, Illinois. “Museum” because most of the “exhibits” are for sale, but it’s neat, I enjoyed it, and the duesenberg collection is a must.

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Navy pier , Shed aquarium , drink some beer play some pinball .

Check out the Uptown arcade on broadway! Tons of vintage arcades and pinballs!

If I was just visiting for a day or two I'd probably be exploring the city and not looking for games, but pinball and cold beer sound like a perfect activity for the hottest part of midday at minimum. I've only looked more into pinball in Chicago because I'm moving there, and knowing its history in the city.

$25-35ish can get you on a tour boat on the Chicago River or out on the lake, which probably feels a lot better than the concrete and steel in the heat.

It's likely to be cooler than the 100+ heat indexes of this last weekend when OP gets to the city, but summer is just getting under way. Of course, stay hydrated if you're out walking the streets.

I'll be making my architecture/food/pinball rounds there likely sometime in August.

Oberweiss ice cream and a Chicago dog.

Pequods (pizza)
Logan Arcade (pinball/arcade/air conditioning)
Hot G Dog (hot dogs; basically the grunt behind the famous Hot Doug's)
Baseball (sports)
Foster Avenue Beach (beautiful Lake Michigan)
Simons or Green Mill (bar/air conditioning)
Music Box (movies)

I like this list a bit better as I usually steer people away from the tourist traps. There are always music fests going on from now thru Septmeber if you like live music. I don’t like deep dish pizza (thin crust tavern style is what the locals all eat). I will say that all of our museums are world class and never get old to me and I’ve been to them all a million times (Art Institute included). It’s a tough city to beat in the summertime.

Have fun!

Bone in ribeye is a must in Chicago.
Chicago Steakhouse - Chicago Restaurant | Gibsons Bar & Steakhouse
https://www.gibsonssteakhouse.com/