Visiting Chicago Late May/Early June with Kids?

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I have a list of what I did when I went two years ago:

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Where did you stay?

We did a trip to Atlanta over spring break and did fine staying 30 minutes from Olympic Park. The hotel costs around Millennium Park are absurd.

The Field museum has a lot of kid friendly exhibits that could take up a solid day, Tilt 360 would be something the 12 yo would get a kick out of, Navy pier is a good stop for the whole family, the “Museum of Ice Cream” is a tourist trap but if you know it’s for the kids going in maybe take the 12 yo…

Architecture Boat Tour, Shedd Aquarium, Adler Planetarium, Skydeck (Willis Tower), Museum of Science and Industry, Lincoln Park Zoo, Millennium Park, Navy Pier, Garfield Park Conservatory, Montrose Beach / Bird Sanctuary, Green City and Logan Square Farmers Markets, Maggie Daley, and Museum of Ice Cream.

All worthwhile stops with kids.

If you and the wife want a little time to enjoy yourselves with the kids, highly recommend Malt Row breweries in/around Ravenswood and North Center. Accessible via Brown Line and an opportunity to see a couple neighborhoods outside the usual tourist areas of The Loop, River North, etc. These breweries are very much family friendly, as well - You'll see a lot of kids running around.

ETA: Recommend checking out my definitive Chicago thread. Ton of information there.

ETAx2: Forgot to add our summer street festivals are a good way to see different neighborhoods. All have sections with activities for kids/families. Looks like you may be here May 29 weekend? Do Division might be worth it. Wicker Park is a great neighborhood and you can stop at Parlor (Division location) for pizza with the kids on their patio. Otherwise, here's the street fest calendar: LINK.

Former Chicago resident here, some thoughts-

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Maggie Daley Playground

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Do this earlier in the day rather than later. Those metal slides can get really hot in the sun.

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Navy Pier

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Overcrowded and overrated

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Millennium Park

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Cross over Michigan Ave to the Chicago athletic Association and grab a drink at Cindy’s rooftop. Phenomenal views. Food is overpriced though so just plan on having a drink.

Other recs: Science and Industry, architecture river cruise, field museum, tour Wrigkey Field (better to do it when they’re out of town because you can go in the dugout and onto the field)

Ride the CTA, especially in the loop. The kids will get some great views and you won’t be stuck in traffic.

One of the best things about Chicago summers are the street festivals. Tons of info on the internet, but you can look into your particular travel weekend and see which ones are happening.

Great food is everywhere, and I highly recommend Sweet Mandy Bs when the kids need a sweet treat.

Oh and go to Portillos but for the love of God do not put ketchup on your hotdog.

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Wed. - Arrive and have Lou Malnati's near Midway Airport

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If your preference is eating near MDW, I'm going to toss a vote in for Danny's Pizza Place. Thin crust reigns supreme for everyone that lives in Chicago. Deep dish is fine every now and then, but very much a "tourist" thing. You can try plenty of deep dish downtown in The Loop and River North.

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I'll be there next week (Wed - Sun) with my wife and "kids" ...they're 23 and 26

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Especially with the age of your "kids," definitely check out my Chicago thread. Plenty of food, drink, and sights recommendations. Here is the link: LINK

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Wed. - Arrive and have Lou Malnati's near Midway Airport. Figure out the logistics of the CTA near our AirBnB (in the Illinois Medical District). I think the Blue line has a stop not far that will get us downtown.

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Few thoughts / questions in this section:

1. Any reason you chose IMD for your Airbnb? My assumption is cost. It wouldn't be my first choice, but you're pretty close to Little Italy and Pilsen. For Italian, check out Tufano's in Little Italy. Pilsen is a historically Hispanic neighborhood that has undergone quite a bit of gentrification over the years. Some really good cocktail bars and taquerias, and a quick hop on the Pink Line at Polk (right next to Rush University Medical Center).

2. Going back to your Airbnb, make sure you board a Blue Line train bound for Forest Park. There are some that finish their route at UIC-Halsted. If this happens to you, it's ~25 minute walk to IMD or quick Lyft/Uber.

3. I will caution this part of the Blue Line run is quieter, as opposed to some of the "it" neighborhoods on the NW side (e.g. Logan Square, Avondale, Wicker Park, and River West). That said, your part of the route is probably a bit more crowded on the weekend with people coming in from Forest and Oak Park. The 'caution' piece comes from the Pulaski and Western stops - You'll be on/off before, but they are the "border" along 290 between Garfield Park and North Lawndale. Not great neighborhoods, so don't be shocked to see a couple sketchy characters. If you're uncomfortable, sit in front car of the train. Had to go over to IMD yesterday for my annual check-up. Was just me and one homeless guy in one of the cars, but he was harmless.

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explore the city after that.

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Again, check my linked thread above. Pretty much everything you'll want to know about neighborhoods to explore but it will take some planning since you aren't technically on the north or northwest side.

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Brunch at either 4th base or Central Standard Crafthouse. Historic Milwaukee Boat tour, Visit Lakefront Brewery or Miller. The Brewers vs. LA Dodgers game.

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Might I suggest Wicked Hop for brunch? Directly across the street from the Public Market, Third Ward is a great area to walk/shop, and Wicked Hop has, in my opinion, the best one or two bloodies in MKE.

If you go to Lakefront, walk across the river to the Lower East side and check out a couple bars on/around Brady, including Wolski's and Malone's. Fantastic dives.

Thanks for the feedback, Hoop!
Yes, cost certainly was a factor in choosing where to stay. My daughter and son were adamant about having their own rooms so the 3BR requirement was getting a bit costly. It seemed safe in the IMD based on what I've researched.
I may pivot and try Danny's as you've suggested upon arrival....I prefer thin crust pizza anyways! You've provided plenty of options for deep dish downtown for the family to try. I've been to Lincolnshire for work so I've had Lou Malnatti's already.
Question for Milwaukee - I have a car and planned to park near American Family Field and Uber to the different spots throughout the day. Is this necessary? Or, do you think there's enough reasonably priced parking near the Breweries, Boat Tours etc.? It doesn't seem like a terribly difficult town to drive around.
Thanks again for all the information! I will be reading through your provided link and filling voids in my itinerary with some of your recs.

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Unless you're tailgating for the Brewers game, I'd consider not renting a car altogether.

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We have a rental car that we'll be driving to MKE from Chicago. I was just going to park near the stadium because that's our last stop before the drive back. I may just try to find something more centralized and walk/Uber from there.

We'll definitely check out the 3rd Ward.

Thanks again, Hoops!

Hyde Park around campus is completely safe, beautiful, and worth walking around. You just don't want to go west on public transportation (to make a connection north going back toward the Loop) if you don't know what you're doing.

There aren't alot of great restaurants in Hyde Park. I'm a fan of Plein Air Cafe. It's an order at the counter kinda place and it'll be busy with students but the vibe is great.

edit: sorry I just realized you said dinner. Plein Air is a daytime spot. Your best bets are probably Medici or Cafe 53 though neither are anything to write home about. With kids, you might wanna do something like Small Cheval.

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We’re going to the Museum of Science and Industry tomorrow morning. I’d love to hang out around Hyde Park, do a personal tour of UChicago, and find a nice place for an early dinner.

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If you're visiting the Museum of Science and Industry, please spend time walking Jackson Park. It's such a space of solitude.

For a nice dinner in Hyde Park, Virtue is one of the very best restaurants in the city right now. You won't get a reservation this late, but walking in at open could be the play. I've been twice and have seen kids both times.

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But when I read about Hyde Park online, I see that it’s considered part of the dangerous area of Chicago? But it’s also one of the nicest areas as well?

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Hyde Park is a fantastic neighborhood. I wouldn't consider it dangerous in the slightest - Trader Joe's, Starbucks, Strings, Small Cheval, etc., being there says what you need to know I wouldn't venture too west into Washington Park, but probably don't have to worry about this, as that's a more intentional thing to do.