I'm glad things turned out well.  I'm sorry I didn't see this until now and wasn't able to try to help you, but it sounded good! (Although, I'm not a Lou Malnati fan. I don't like their pizza.)

We are back and successfully navigated eating out.  We stayed at The Drake Hotel (beds are too soft, but that's a different story).  Their breakfast only had nuts listed as an add in for Steel Cut Oats.  DS ordered pancakes both mornings (there was a buffet, we did not check out the baked goods to see if there were any nuts in the breakfast pastries).  Because we ate such large breakfasts, I just brought sandwiches and snacks for the kids in my backpack to the Museum of Science and Industry (expensive but great).

Anniversary dinner was at The Capital Grille.  We had a preset menu in a private room.  I gave them a list of the items that DS would be eating off the menu ahead of time.  We picked up Nut-Phree's cupcakes at a local market the day before so DS would have dessert. 

Sooooo, the one thing that I was surprised by (but was informed immediately by the head waitress for our party) was the bread basket.  We don't eat out a lot, and always refuse the bread due to DS, but also because DH and I don't eat bread.  There, of course, in the basket was a roll with sesame seeds.  I was a little disappointed, they certainly could have left out that roll and filled the basket with more of the other types.  I will be letting the event planner know so they can be aware of it in the future.

Dinner is on Tuesday.  We are a party of 23 (yikes) in a private room.  The chef has a list of items that DS is going to eat.  No items on our private dining menu contain nuts or sesame including the desserts, but since that is the biggest risk of cross contamination, we will bring DS a Nut-Phree cupcake that we can get at a local market.

Monday night we will eat at Lou Malnati's...desserts are not safe, but everything else is ok.

I have a call into the hotel restaurant that we are planning to eat at for breakfast.  Only nuts listed on the menu are in the steel cut oats, will have to check on the baked goods, but I think we should be ok with pancakes.

We have a date, now all I have to do is find the restaurant and figure out how many people are coming.

Thanks for all the suggestions.  DH will have a schedule soon for August so then hopefully we can pick a date.

You might want to check into Chez Moi -- it's north of downtown and French.  The chef's kids have food allergies and staff is very aware.  Last we were there, no tree nuts on the menu (not sure about sesame though).

I don't know about sesame, but you might want to try calling Giordano's, Gino's East, Gibson's Bar & Steakhouse, and Grand Lux Café. Grand Lux was especially good about making my dish peanut-safe. Those places should be able to accommodate large groups with a reservation. Pizzeria Uno or Due might work too, but the restaurants are a little tight. I've heard Maggiano's is pretty good with allergies too but I've never been.

We are talking about using points to stay at The Drake.  So within walking distance or short cab ride would be ideal.  Not necessarily picky on type of food, kids will be with us so has to have some relatively normal choices and obviously somewhere that can deal with a treenut and sesame allergy.

Hmmm. Need more info. Type(s) of cuisine preferred? Cost preference? Downtown area or further north or south?

Ok, raising this thread. 

In laws will have been married 50 yrs in November, which is not a great month to celebrate due to Thanksgiving.  We are hoping to do a weekend in Chicago and go out to dinner sometime between now and November.  May be able to have other relatives to live in the area meet us for dinner, could be anywhere from 6 to 30 people. Other than the restaurant listed above, any other suggestions?

We do have a thread or two about Chicago restaurants, and if I get the chance, I'll link to them here. Not sure if they'll be of help--if they have a party room that you'd probably be looking for. 

I would second the Italian Village - good food and a great (educated) staff.

Before I even worried so much about having a TNA, my mother and I both had shellfish allergies.  They always accommodated us no problem and we went there plenty when I lived in the area.  They also dealt with a friend who had a peanut allergy with good results recently (I rec'd them).  I wish restaurants in my current city were so helpful!

Italian Village has been awesome every time I've gone there with nut allergies (once the chef came out and told me he couldn't guarantee the sausage in my pasta had come from a place with no nuts so would I prefer the meatballs which are made on site). There are three seperate restaurants in Italian Village, all are equally good but I think The Village upstairs is just gorgeous. http://italianvillage-chicago.com/

My parents are looking at having an anniversary dinner at a restaurant, one preferably with a smaller room to reserve.  Has anyone had any sucess with a restaurant they could share?  Of course preferably nut free (we are PNA and TNA) but know that is hard to find!  Or at least one that had good allergy procedures in place and you felt comfortable with.  I figure if we can't find a place, then we would just bring his own food in.  Thanks for any information you can share!