We arrived in Chicago after a harrowing drive. Following a gas tanker truck on the interstate, and literally could barely see his taillights. Why does this keep happening? I hate it. And the traffic getting in to the city-yikes! We could not begin to understand why Chicago was SO much more expensive than New York, and everyone knows I LOVE NEW YORK CITY! Well it turns out there was a big Lollapalooza concert in Grant Park. Oops.

We checked in to our hotel in the North River section and loved the area. It is so strange that there are so many short buildings in Chicago. I kept thinking this was not the highest and best utility for the property (real estate background talking). But, it was strangely comfortable, in that you felt a sense of openness, that you only get downtown in NYC. There aren’t the constraints of land here. Not an island. It just spreads out this way and that.

We checked in with Elliot Drabs (who we love), and let him know we were in for the weekend and that we wanted to meet him and his wife for dinner if at all possible. He was amazing. He sent us a list of must do’s and we made plans to have dinner on Saturday night.

For Friday night, we checked Yelp for some dinner suggestions in the area and decided on either Gallery Bar or J Rocco. Everyone talked on Yelp about how great the Ahi Tuna nachos were so we thought, okay, sounds delicious and healthy….kind of. And of course, they changed the menu, without changing anything on their site and what they did have sounded not so good. So we decided to go with Italian which we were really in the mood for too, and were so glad we did! The food was delicious, but, the service was spectacular. We absolutely fell in love with our server, Chase, and his general manager, Jodi, as well. Chase told us what we must do in Chicago, and it was exactly what Elliot already told us, so he immediately cemented his credibility. I wish every restaurant would understand the fact that you must have a great team of servers, or your food alone, will not bring people back. Be good to these people. They are essential to your success.

On Saturday morning we took a taxi to the Field Museum for the exhibit on the 1893 World’s Fair. Rick and I read a book called “Devil in the White City”, which was all about the 1893 World’s Fair, so we really wanted to see this. We really enjoyed it and wandered around for hours, and fit in a Chicago dog at Kim and Carlo’s. We decided to head over to the Architectural Boat Tour next, again on Elliot’s (and Chase’s) suggestion. We were so disappointed to see that they were sold out for the day, which was surprising, since it seemed that everyone was at Grant Park for the concert. Again, on to plan B. The top of the Hancock Building for a cocktail and a view of the city from the 96th floor. Check.

At 8:00 p.m. we met Elliot and Nara at the rooftop bar at the Godfrey, which was a great place, but, umm, I could have given birth to 98% of the people there. The people downstairs gave Elliot and Nara a hard time on the way up, do you have reservations, etc. He told them we are meeting an older couple (ouch. Accurate, but ouch. Thank god we always feel younger than we are…), a tall guy, and the guy said “oh yeah, go on up.” We moved on to The Kerryman, a little Irish Pub, for a quick drink before heading off to Topolobampo for dinner. This is an amazing Mexican (not taco/chimichanga-more Poca Cosa-but fancier) restaurant, it is one of the Obama’s favorites. It was incredible. You choose 3, 5 or 7 dishes. We all went for 3, and I couldn’t even finish 3, so was quite pleased that I didn’t choose more. Heck, it was difficult enough. What a menu. And don’t even get me started on the Margarita’s…… Sat next to a nice couple of guys, that we really enjoyed talking to also. We finally got back to the hotel after 1:00 a.m.

We considered getting up early and trying to get on the Architectural Boat Tour, but didn’t. Now we have a reason to go back. We stopped in at Elliot and Nara’s to say goodbye and headed to points north. Stay tuned. In the meanwhile, some photos…