First Time in Chicago: Suggestions?

This thread is gold, heading to Chiraq tomorrow for a nice little 4 day extended weekend. Got real lucky, I read an article on Aug. 21st about how Aug. 23 is the cheapest day to book plane tickets due to the post-summer slowdown which typically means sales. Checked Southwest on the 23rd and used my points to book the equivalent of a $120 roundtrip nonstop flight out of Reagan. So I'm flying to Chicago for free. If nothing else, it's worth it for that alone.

Dude. What a deal. I did a few of the things mentioned here. Definitely do the hot dog. Went to a brewery called half acre which was great and close by is their consensus best Chicago dog. Staying on the magnificent mile? I walked on the lake to the zoo which was pretty bad ass too.

Yeah the blue V hot dog cart is on my "keep an eye out" list. And I'm torn between Lou Malnati's and Ord Pizzeria, I looked at pictures of their pizza online and it looks pretty damn good. My neighbor told me to go to Superdawg drive in for a hotdog but idk if I'm gonna go all the way up there, I might just hit up a street cart if it's more convenient.

My other neighbor (born and raised Chicagoan) gave me a pretty comprehensive list of things to do and places to eat.
Gene and Jude's - for hotdogs
Portillo's - get the "combo" (http://www.portillos.com/menu/restaurant/beef-and-sausage-sandwiches/##ComboBeefCharGrilledItalianSausage) which is apparently a beef/italian sausage sandwich on a hoagie roll that looks pretty good, and apparently it's a local favorite.
And if I have a classier tastes "Girl and the Goat" yes that is the actual name lol.

As far as things to do he highly recommended the Chicago Architecture River Cruise, which for 33 bucks seems very reasonable so I'm probably gonna do this one. Not to mention the Sears Tower but only if there's no fog, otherwise I'm wasting my time. And according to him when he was growing up there (70's/80'sish) authentic Chicago style pizza was a thin crust made with cornmeal, so I'm gonna keep an eye out for that. And if I have more time left over walking along the lakefront trail sounds pretty cool, along with the Museum of Science and Industry which is right up my alley.

Dude. What a deal. I did a few of the things mentioned here. Definitely do the hot dog. Went to a brewery called half acre which was great and close by is their consensus best Chicago dog. Staying on the magnificent mile? I walked on the lake to the zoo which was pretty bad ass too.

TMC did you end up doing the architecture boat tour at night? I'm headed there in October and that looked pretty cool to me as well.

Yes I did. My wife's boss's brother lives in Chicago and he says they love it so much they go at least once a year. I thought that was pretty rare for someone who lives in the town.

Also, I did enjoy some authentic deep dish, but the brother recommended this: Chicago Pizza And Oven Grinder Co. | Chicago Pizza Company (http://chicagopizzaandovengrinder.com/)

It was freaking amazing. I dare say better than the actual deep dish. Warning: get there early or be prepared for waiting 1-2 hours. He said this was normal on weeknights!

http://chicagopizzaandovengrinder.com/wp-content/uploads/2016/08/int_192-2-e1476376376300.jpg

For dinner, we did The Purple Pig which was one of the best restaurants I've ever been to. I think the winner of Next Iron Chef (or something like that?) owns it. It's just down from the docks, so you could grab dinner there and then go to the boat tour. Also, grab a drink on one of the rooftop bars.

Looked at my photos and the place for the Chicago Dog is Byron's.

https://static1.squarespace.com/static/5613142be4b0fb1f506c05b7/t/56132ca2e4b02bdcb2d68023/1444099266209/

Had a great time and it knocked San Diego off the top of my list as my favorite big city. That being said, when we got home we heard about seven people were murdered after we left, so there's that. I went to 3-4 different neighborhoods and walked them all, felt safe the whole time. One recommendation is if you're by yourself, wear headphones because there were a ton of random people who come up asking you weird ass questions trying to get some money.

Yeah the blue V hot dog cart is on my "keep an eye out" list. And I'm torn between Lou Malnati's and Ord Pizzeria, I looked at pictures of their pizza online and it looks pretty damn good. My neighbor told me to go to Superdawg drive in for a hotdog but idk if I'm gonna go all the way up there, I might just hit up a street cart if it's more convenient.

My other neighbor (born and raised Chicagoan) gave me a pretty comprehensive list of things to do and places to eat.
Gene and Jude's - for hotdogs
Portillo's - get the "combo" (http://www.portillos.com/menu/restaurant/beef-and-sausage-sandwiches/##ComboBeefCharGrilledItalianSausage) which is apparently a beef/italian sausage sandwich on a hoagie roll that looks pretty good, and apparently it's a local favorite.
And if I have a classier tastes "Girl and the Goat" yes that is the actual name lol.

As far as things to do he highly recommended the Chicago Architecture River Cruise, which for 33 bucks seems very reasonable so I'm probably gonna do this one. Not to mention the Sears Tower but only if there's no fog, otherwise I'm wasting my time. And according to him when he was growing up there (70's/80'sish) authentic Chicago style pizza was a thin crust made with cornmeal, so I'm gonna keep an eye out for that. And if I have more time left over walking along the lakefront trail sounds pretty cool, along with the Museum of Science and Industry which is right up my alley.

Definitely do the trail. Was able to walk in the lake for a mile or so. Let me know how the museum is because that was the one place on my list I didn't make it to.

Chicago is 3rd on my food city list behind NY and New Orleans

This thread is gold, heading to Chiraq tomorrow for a nice little 4 day extended weekend. Got real lucky, I read an article on Aug. 21st about how Aug. 23 is the cheapest day to book plane tickets due to the post-summer slowdown which typically means sales. Checked Southwest on the 23rd and used my points to book the equivalent of a $120 roundtrip nonstop flight out of Reagan. So I'm flying to Chicago for free. If nothing else, it's worth it for that alone.

WTF?? $120 ... ive had chicago on a food destination list for a while. That and Austin, TX. Amazing deal.

Thanks TMC! Looking forward to trying all of it!

Well I did make it to the trail, didn't make it to the museum though. :/ Love the place and will definitely be back eventually if I ever catch another good deal, so it's back on the bucket list. As far as cities go it's up there with NYC/Boston, there's no shortage of random things to do if you have the time. Traffic sucks, but it's par for the course.

As far as food goes, I went to several local hotspots and for the most part have nothing but nice things to say about them.

Portillo's - the combo is legit. I only wanted the six incher (that's what she said) but the guy taking drive through orders in the parking lot (literally that bitch put Chik-Fil-A's line to shame) suggested I get brown gravy on the side (not normal brown gravy either, this was like some mildly hot/not thick with all manner of spices/seasoning) and it came out muy bueno.

Harold's Chicken Shack - decent tenders, mild sauce is alright, fries are meh

Culvers - if you've had Freddie's Steak Burgers don't bother, the "butterburger" tasted the same.

Superdawg - tourist trap, decent Italian sausage but not worth the drive or the insane wait times.

Ord Pizzeria - Great recommendation by Schneed, very good, delicious thin crust pizzeria. Worthy of the trip. If you love crust don't bother.

Chicken-N-Spice - not necessarily Chicago, but I ate at this place in Joliet and the brand lives up to the name.

Gold Coast Dogs - I ate at this place in Midway, and the staff assured me they used Vienna beef, even though I didn't see the blue V anywhere. I had the Chicago style char dog, and even though I'm not a huge hot dog fan I can see why people like it. Their hot dog game is on point, definitely recommend.