Three days in Chicago: Where should we stay? What should we do? What should we eat and drink?

[methodology]

Can’t recommend any specific places but best Mexican food I’ve ever had (I’ve had Mexican in Arizona, Texas, New Mexico, Cali) was in Chicago

 

[storrsroars]

Can’t recommend any specific places but best Mexican food I’ve ever had (I’ve had Mexican in Arizona, Texas, New Mexico, Cali) was in Chicago

I believe this to be true. SoCal beats just about anywhere with food trucks and taco stands, and certainly fish tacos, but honestly, good tacos can be had in just about any decent sized city these days. For "modern" sit-down Mexican, and traditional south/central Mexican mom & pop joints, Chicago is the king.

 

[Madmannsucks]

Buddy Guy's legends. Find out if he is in town. If so he will most likely be there and play. If you buy his book he will sign it and take a pic with you.

 

[VKong]

Both have been mentioned, but Pequod's is one of my fav pizzas in the country and I'm a New Yorker. Original Kuma's corner is a fun place for burgers and the last time I was there they had Jamo on tap!

 

[businesslawyer]

Thanks. Very much appreciated.

Yeah I was a bit surprised by the prices at Palmer House and Raddison Blu. Both $450+ per night. I’ve been looking at AirBnBs because we‘ve had very good luck with them elsewhere (I read the reviews and stick to Superhosts) and they seem plentiful and very reasonably priced by comparison. We like living like locals. We don’t mind using public transportation or Ubers to get to places we should see and things we should eat. With that in mind, how are the following neighborhoods to stay in:

Wrigleyville
Pilsen Historic District
East Village
Lincoln Park
West Town

We have to at least try deep dish. Peqoud’s? I definitely want to know about the Italian beefs and breaded steak sandwiches too.

I’ve been known to travel for a good dog: I just chuckled watching the All-Star Game because they did a little feature on Pink’s, which I death-marched my family to on a hot, dry and windy day, thinking it would be a much shorter and nicer walk. It was like two miles on a crappy, busy street with bad or no sidewalks. They all cursed me, but everyone was happy once we were there.

I have given up on having "favorite hotels" any more. I just go onto Kayak and try to find a very good hotel that is priced lower than others.

 

[8893]

I have given up on having "favorite hotels" any more. I just go onto Kayak and try to find a very good hotel that is priced lower than others.

Yeah I did the same on Hotels.com this morning and it looks like there are some other good options with better prices.

I'm still intrigued by a lot of the AirBnBs though; there are more nice ones than I've seen in other cities, and the ones we've stayed in in Baltimore, San Francisco and the Bahamas have all been really great.

 

[WNConn]

Let me know if you need recs on good hookers brother

 

[8893]

Let me know if you need recs on good hookers brother

I just booked a long weekend in Chicago for my wife and me

 

[businesslawyer]

He obviously meant "good, discrete hookers." Give him a break!

 

[HuskyHawk]

Yeah I did the same on Hotels.com this morning and it looks like there are some other good options with better prices.

I'm still intrigued by a lot of the AirBnBs though; there are more nice ones than I've seen in other cities, and the ones we've stayed in in Baltimore, San Francisco and the Bahamas have all been really great.

It's a really physically large city. Not like San Francisco or Baltimore in that way. So I'd say trust @superjohn because location will matter quite a bit. The L is pretty dense in the loop, but less so as you move further out. We stayed at the Silversmith last time. Great location to get to anywhere (and the urban Target nearby proved useful). Previously stayed a little north of there, a block or so off Michigan, and that was nicer, but maybe less convenient to explore.

It's too bad baseball season will be over. One of the most fun things I did in Chicago was a pub crawl from Wrigley back to my friends' house. If Wrigley does tours like Fenway does, I'd still go see it and check out the neighborhood. It's a really cool area.

Agree with everyone on the architectural boat tour. Gino's East is my choice for deep dish (enjoyed with a local), but I haven't had Pequods. I think you can skip the Navy Pier, not that anybody suggested it.

 

[Adesmar123]

Is UConn recruiting any "Dion" in Chicago. Just met an AAU team at the airport and met a "Dion" (sp?).

 

[QDOG5]

Is UConn recruiting any "Dion" in Chicago. Just met an AAU team at the airport and met a "Dion" (sp?).

I think he's already picked his school. He's going to Belmont.

 

[8893]

It's a really physically large city. Not like San Francisco or Baltimore in that way. So I'd say trust @superjohn because location will matter quite a bit. The L is pretty dense in the loop, but less so as you move further out. We stayed at the Silversmith last time. Great location to get to anywhere (and the urban Target nearby proved useful). Previously stayed a little north of there, a block or so off Michigan, and that was nicer, but maybe less convenient to explore.

It's too bad baseball season will be over. One of the most fun things I did in Chicago was a pub crawl from Wrigley back to my friends' house. If Wrigley does tours like Fenway does, I'd still go see it and check out the neighborhood. It's a really cool area.

Agree with everyone on the architectural boat tour. Gino's East is my choice for deep dish (enjoyed with a local), but I haven't had Pequods. I think you can skip the Navy Pier, not that anybody suggested it.

Yeah I have dug a little deeper for still very good, but smaller and lesser known hotels in the same general area that @superjohn recommended and there are some better deals to be had. I gather that the price hikes in some of the others is in large part due to convention season. I have my eye on Hotel Julian at the moment (in-room Nespresso machine is a nice bonus for me).

I checked the Wrigley website this morning to see about tours. Looks like they end October 2nd, which is too early for us. I'm hoping we'll still end up in the neighborhood at some point.

 

[Adesmar123]

I think he's already picked his school. He's going to Belmont.

Thanks! Full name?

 

[8893]

Thanks! Full name?

Dion Francis DiMucci

 

[QDOG5]

@8893 lot's of good advice already. A boat tour of the lakefront and the river is excellent. A stroll to the Bean and Maggie Daley park is fun. I would suggest doing the river walk also. Wrigley tour is a good idea( I called the box office and they said the tours continue through October although the dates on the website won't appear until August?). Going to a blues club is fun. Second City is iconic. I would definitely attend a show. Skip the hot dog but have the Italian beef with giardiniara. So many good restaurants. Girl and the Goat is a personal favorite. For drinking you'll have to make your way to Rush and Division Streets. Way past it's heyday but still very Chicago. Butch McGiure's and The Lodge are institutions.

 

[8893]

Wrigley tour is a good idea( I called the box office and they said the tours continue through October although the dates on the website won't appear until August?)

Thanks! That's great to know. Will definitely do that if available.

 

[bristol rises]

Twin Anchors in Old Town for ribs. IDK they are open for lunch during week but perhaps on weekends.

Not a fancy place when compared to what other posters' recommended, but an institution.

 

[bristol rises]

Additionally, if you are walking around the Loop in general vicinity of Sears Tower (now Willis), a stop at Old St. Pat's Church and Union Station may be cool to admire the architecture. Old St. Pat's was one of only a handful of structures to survive the Great Chicago Fire.

 

[Deepster]

We have to at least try deep dish. Peqoud’s?

Going on record to say you'll regret this. If you absolutely must do it, get it at the end of your night so you can waddle back to your hotel and go to bed. Otherwise, you are not going to feel like doing anything else, even if you only eat one piece.

Tried two different spots in my various visits. Never again. It's a sloppy melted cheese casserole.

 

[8893]

Going on record to say you'll regret this. If you absolutely must do it, get it at the end of your night so you can waddle back to your hotel and go to bed. Otherwise, you are not going to feel like doing anything else, even if you only eat one piece.

Tried two different spots in my various visits. Never again. It's a sloppy melted cheese casserole.

In the name of science, I think I need to at least taste it.

 

[HuskyHawk]

Going on record to say you'll regret this. If you absolutely must do it, get it at the end of your night so you can waddle back to your hotel and go to bed. Otherwise, you are not going to feel like doing anything else, even if you only eat one piece.

Tried two different spots in my various visits. Never again. It's a sloppy melted cheese casserole.

My first time in Chicago, my guide (law school classmate from the south side) insisted that we go to Gino's East. Even as 20 somethings we had lots of extra pizza, and since we went straight to N. Rush street for a night of drinking and memories we carried the box and gave it to a homeless guy. Never seen a homeless guy so thrilled to get anything. Calories for the week.

I like to think it provided nearly ideal alcohol mitigation that night, which was certainly needed.

 

[Adesmar123]

Dion Francis DiMucci

AKA The Wanderer?

 

[storrsroars]

Girl and the Goat is a personal favorite. For drinking you'll have to make your way to Rush and Division Streets.

That place intrigues me. Have you had the pig face, and is it cheeks or something else?

 

[BigErnMcCracken]

That place intrigues me. Have you had the pig face, and is it cheeks or something else?

I could be mixing this up with another place but as I recall it comes in patty form and is basically an agglomeration of various pieces of meat and fat from the face. I was sort of hoping for a braised head to be delivered to me to pick at but it wasn't that if I'm remembering the right dish.