Your must eats in Chicago, new York and Boston.

Parts of Kenna-brah and NO East can be just as dangerous as Chicago. The City is perfectly fine especially if you know where you’re going. I’ve been to Chicago a half-dozen times with my wife and 2 teenage kids and never felt unsafe. Several times we stayed at hotels near O’Hare and commuted around the entire city via the CTA - Chicago transit authority… bus, train, subway. 3-day unlimited pass is around $12 per person. One Uber trip or downtown parking will cost you $45. Bring comfortable tennis shoes as you can walk everywhere and use the subway for longer commutes.

Pequods is near the Lakeshore, Navy Pier, Millenium park area, probably 5-6 blocks from Lincoln Park Zoo. I would definitely do Wrigley Field Cubs game, Architecture River boat Tour, and The Bean (millennium park) if your time allows.

Chicago is an amazing city with endless food choices. Definitely get you a Portillos polish sausage hot dog and an Italian beef sandwich. Lou Malnattis pizza is also very good.

Cozy Noodles & Rice is an Excellent small Thai restaurant on Sheffield, about two blocks south of Wrigley Field.

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I have family telling me not to rely on public transport. So I have a car service from the airport.

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From the airport, yes, I agree. Once your in the city, the public transport is preferable to Uber or whatever in most situations.

I've been in Chicago for two weeks this month.

My wife used to live in Boston and we still go on "let's go to all our favorite restaurants" trips there. A lot of my favorites went out of business during COVID or have changed management or menus. But of the survivors, Coppa is way up there. Whatever's seasonal on the pizza or pasta section is always great -- we usually go in summer so that usually means something with corn or squash blossoms --- and the uni sandwich is my number one favorite thing I've had in the city. If you're an amaro fan, they have Varnelli's Dell'Erborista, which is my personal favorite and hard to find, at least where I live.

Flour in Cambridge is great not just for the sticky buns but for, if they have it, the lamb sandwich. (Every sandwich I've had there is great, but my wife hasn't lived in Boston for ten years and we still talk about the lamb sandwich.)

There are some good places in Boston's Chinatown, but if you're going to NYC too, Boston just isn't going to compare, at least in terms of selection.

I really like Darbar (Pakistani) and Thai North (... Thai). There are apparently a number of Nepali restaurants in the city now that used to be limited to the outskirts -- I haven't been, but I hear good things.

Toscanini's for ice cream is an absolute must -- especially since you'll be there in summer. There will be a line. Someone will tell you it's not actually worth it, that X or Y is just as good or better. But I'm telling you, every time we go, it's better than we remember. Try a couple different flavors before you order. Somehow, any flavor that is related to a beverage -- not just the coffee or tea flavors, but wort -- always ends up being my favorite thing we get. And the line moves pretty quickly.

These recs are pretty spread out geographically, but Toscanini's is really worth the trip if you're not staying nearby.

Now that my favorite burger in the city is gone, Flat Patties and Tasty Burger both do a really good one. Nothing fancy, no short rib on top or anything, just really good.

Someone will probably try to sell you on a lobster roll, and I don't know, if it's your thing, I guess this is the place and the time to get it. I personally always feel let down by them -- New Englanders pride themselves on barely seasoning their seafood so you don't "cover up the flavor," but if they'd boil that thing like a crawfish I think it'd be a huge improvement. They're really expensive for the amount of lobster you get, especially in the city.

as a tourist who has been to the city many times, the CTA Rail system is hard to beat and very affordable. The 3-day unlimited pass will allow one to navigate the entire city via rail or bus. I grew up in NOLA and my only experience with "the subway" was watching TV sitcoms and movies filmed in the city: Blues Brothers, Spider Man, Planes Trains & Automobiles, Ferris Bueller, Good Times, Dark Knight, etc... Walking along these same scene locations was pretty cool.

Chicago: Bavette’s, Ciccio Mio

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Is no one a Girl and the Goat fan in Chicago anymore? Last time I ate there, I really enjoyed it.

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I'm still a fan. My wife and I go every few months. I only avoid it in my recommendations because it's in every other post on Chicago threads

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Is RPM Italian worth trying?

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To be honest, I've never been... Sort of stick with La Scarola and Piccolo Sogno in River West when I do Italian. If you prefer West Loop, I'd go Monteverde over Formento's. Something off the beaten off would be Tufano's in Little Italy near UIC. Very local, casual place - good food and it's hard to beat the price.

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Toro

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I have to be honest, used to be one of my favorite restaurants but I feel like it’s gone very downhill. I wouldn’t recommend anyone going there these days.