Although another poster calls Lou Mitchell's a waste of time, in his usual courteous way, the place has great Chicago atmosphere, as does Manny's.

Great places with long waits (go outside peak hours)
Purple Pig
Fat Rice
Hot Dougs

Great places without such large mobs
Yusho
Sepia
Naha

Chicago classics
An Italian beef at Al's on Taylor followed by an Italian lemonade across the street at Mario's
Deep dish pizza at Lou Malnati's
Corned beef sandwiches at Manny's
Omelets at Lou Mitchell's

I think you'll enjoy the three places you've already selected.

Thanks for the detailed report.
I agree that Mastro's sucks. Glad you had lots of good stuff elsewhere.

Yaki, good on ya for all the work you did into putting together this itinerary. While I might quibble with a couple of your choices, I'm a believer in the karma of following through on your own plans unless there are strong objections. (None here.)
Please report back, and I hope you have some great meals!

Since you like two of my favorites, Hole in the Wall and Nhu Lan, let me try to help. Here are some eclectic suggestions.

La Chaparrita measures up to San Diego tacos, in my book.
Make the trek down south to Zaragoza for birria. Also consider Los Gallos #2 for a bowl of carne en su jugo.
Do the Beijing duck dinner with a couple of friends at Sun Wah.
Polish homestyle cooking at Smak Tak.
Neapolitan style pizza at Pizzeria da Nella.
Chopped brisket at Smoque BBQ.
Vietnamese at Nha Hang Viet Nam.
Other places: Aroy Thai, Vie, Santouka ramen at Mitsuwa, Khan BBQ
Hope you find some winners in this thread.

Indeed, as nsxtasy says, Hotel Sax is near tourism central on N. Michigan. As an example of the type of neighborhood this is, Donald Trump's Tower is two blocks away.

But that does mean you are in a great location for restaurants. Two that are very close to the Sax that you can add to your list are Naha and Sunda.

Yes, Briansy, Hot Doug's is worth the effort. You asked about Chicago "institutions." This is definitely one of them.

I would suggest basing yourself at a bed-and-breakfast in Wicker Park, since you find hipster joints friendly to out of towers, which I think you will find to be true here as well. I sent friends to House of Two Urns last year and they enjoyed it.
Random suggestions based on your post:

Hot Doug's at about 2 p.m.; a local institution for upscale hot dogs (avoid during lunch rush; also, closes at 4 p.m.)

Spend a day at the Art Institute and have lunch at Terzo Piano in the contemporary wing. Walk through Millennium Park afterwards.

Toon's for conversation with locals; have chicken wings and whatever is on the specials board

Delicious cocktails at The Violet Hour and/or Scofflaw's; not divey but highly enjoyable

Chinatown Square Mall in Chinatown

Argyle Street for Vietnamese

Wicker Park/Bucktown and nearby:
The Bristol
Owen & Engine
Whistler (bar)
Bang Bang Pie Shop

Also consider spending a day at the Museum Campus, where there is a natural history museum, an aquarium, and a planetarium. Hike back to Michigan Avenue for decent Irish fare at The Gage, or hit Heaven on Seven for Cajun

North Michigan Avenue is the tourist mecca and can turn into a Buckhead redux if you don't choose wisely. But there are several good places around there that should pop up in some of the threads already mentioned.

It would be helpful to know what area you are staying in.
Italian restaurants near N. Michigan Ave. with good food and cool scenes include RPM Italian and Siena Tavern.

You mention sausage in your opening post. My Polish relatives much prefer the Polish sausage at Andy's Deli to Bobak's. Andy's online store is having a spring sale now. 30 varieties of Polish sausage to choose from!
http://www.andysdeli.net

A Manny's corned beef sandwich is certainly a Chicago specialty. There's a location right there at Midway.

If you ever find yourself in a situation where you've gone way too long without eating, get to this place and try the Atomica. An amazing piece of work.

Thanks so much for the reply! Sorry that I didn't give you more time to recover from your journey! ;->

So tell us about your trip. I trust you enjoyed seeing the Bulls end the Heat's winning streak!

Just southwest of Chicago in the suburb of Summit is Grand Duke's. Some of the entrees are mainstream, but the atmosphere is great.
A little further out and a little more authentic is Cafe Smilga in Darien.

If you're not wedded to the idea of Mexican, I'm seeing availability at Naha at that time, if we're talking this weekend. At the high end, Sixteen also has slots.

Please post your opinions on places even if it means starting a new thread--maybe a weekly roundup or something. The more voices and opinions, the better.

That seems harsh. He liked Southport Cafe and La Chaparrita. I give him credit for getting out and trying our recommendations.

Low-brow Middle Eastern = Noon O Kabab on Kedzie
Low-brow South Asian = Ghareeb Nawaz on Devon
Vegetarian Indian = Uru-Swati on Devon
Vietnamese = Nha Hang Viet Nam on Argyle
Thai = Aroy Thai on Damen
Farm to Table = Lula Cafe on Kedzie

The Wikipedia photo doesn't give a very good sense of perspective. The pics around the border of this page do:
http://www.alsbeef.com/
As others have said, it's big, but not that big.

After dinner, you might consider enjoying some music at Buddy Guy's, just a couple of blocks from your hotel.

My two cents: I would choose Original Pancake House. My one trip to Jam was very disappointing. I was served pork cheeks that were nowhere near fresh.

In this situation, I tend to go with the other party's suggestion unless I have strong objections. Since I think Graham Elliot has been more up than down as of late, I would stick with that.

I think they've gotten lazy about pastor at TC. They have more business than they used to, and it seems as if they are now cutting the trompo in advance of the lunch rush. Didn't used to be that way. Sort of a victim of Internet acclaim, I guess. Can't believe they didn't at least griddle the pastor meat. Sorry you missed them when they were at their best a couple of years ago. Thanks for taking another one for the team.

I'd vote for Mercat a la Planxa or Vivere as your fourth place. I don't see anything wrong with two Italian places on your itinerary (Tesori and Vivere).

Your choices are much better than your client's.
Another possibility would be Shaw's Crab House.
Or, closer to the theater district, Vivere.

I'd walk west a few blocks to Maude's Liquor Bar after Blackbird.
If you want to stay in the downtown area on Saturday, you can get your hot dog at Portillo's.
If you're hitting Girl and the Goat, no need to hit Little Goat the very next morning. Either of the other two places you mention is good for brunch.

I would hit Moto for an early dinner. I'm sure they would be happy to speed up the pacing to accommodate your little one.

Tends to be a bit more consistent, but if you're close to one of the others and it's more convenient, you'll probably still get a good bowl.
Oh, and hit Birrieria Zaragoza if you like goat.

Thanks for the heads-up. Glad someone else here is a big taco fan.
Since you seem to enjoy authentic Mexican street food, try the carne en su jugo at Los Gallos #2 if you get the chance.
4252 S. Archer