“Big shots at da Conrad!”  That’s how my good buddy Kyle described my girlfriend and I in his thick Chicago accent when he saw our room at the impressive AAA Four Diamond Conrad Chicago on Rush and Illinois. Kyle joined us at the hotel to watch the Cubbies on our room’s awesome 50-inch plasma TV. 

We didn’t make the game this year, but the last time I was in Chicago Kyle and I caught a game and went on the Wrigley Field Tour.  Both the game and the tour are highly recommended.  I even shed a tear when I first saw the Friendly Confines. And no, it wasn’t after the Cubs lost in the playoffs last year. This year I decided to take my best gal and see more of what Chicago has to offer. 

Kyle picked us up from the airport and drove us up to his neck of the woods on the North Side to a neighborhood called Lincoln Square, not to be confused with trendy Lincoln Park.  Lincoln Square is really not THAT far north, but it’s apparently a little cheaper than Lincoln Park and Wrigleyville, where fellow blogger Nancy Jones visited.

The next day, my lady friend “had” to go to H & M on the Magnificent Mile - some sort of European Hipster multi-level clothing store.  After I realized I was too old to be in there, I went outside for some air and to people watch.  As I looked to my left I saw “Honorary Mike Ditka Way,” a road sign that commemorates the Super Bowl-winning coach and perhaps his swanky restaurant.  That eased the pain of waiting, since I couldn’t find any of those traditional “man chairs” usually seen at malls.  We didn’t make it to a lot of fancy stores on our trip (thankfully), but there were plenty to choose from on The Magnificent Mile.

After our shopping trip/boyfriend torture we walked down to Clark and Ontario for lunch at Portillo’s, a a good One Diamond place Kyle had said offered all types of Chicago staples like the Italian beef sandwich and the Chicago-style hot dog, both of which were ordered and devoured quite easily.  It was a little loud in there but we were sitting close to the lady at the counter shouting order numbers and asking over the microphone, “Where you from?  Orlando?  Orlando’s in the house!”

Now if you’re planning on going to Chicago, be prepared to do some walking.  My girlfriend and I live in Orlando, Florida - the land of cars, escalators, and elevators between floors one through three – so her feet took a beating in Chicago. Some Band-Aids were desperately needed from the local Walgreens, which by the way seem to be on every corner downtown, making staying downtown very convenient. After her feet were taken care of, it was on to the “L” and off to Chinatown, only about five or so stops south of the Downtown Red Line Grant station.  We weren’t overly impressed with Chinatown, but it was worth seeing another part of the city and we never felt unsafe.

The weather was so overcast and hazy that we couldn’t even see the tops of the skyscrapers. But by Friday afternoon it started to clear up, so we dashed over to the John Hancock Observatory.  The earlier clouds must have scared people off because by the time we got there, there was no wait, no lines, and hardly anyone taking in the breathtaking views 94 stories up.  We ended up staying there quite a while just taking in the skyline.  It has tables and chairs to relax in and even a small cafe.

That Friday night we attempted to get into Giordano’s on Rush and Superior, but I’m not too keen on waiting an hour and a half for a meal.  Pizzeria Due was a short walk from Giordano’s and the wait was only about 20 minutes. Since it takes so long to cook a deep dish Chicago style pizza, you have to order it when you put your name on the waiting list.  Much to our dismay, the pizza was over-cooked and the crust was burnt and way too hard.  Thankfully, the salad we shared was fantastic and so was the Spumoni dessert.

Saturday, we took the 60-minute Wendella Architecture Tour on the Chicago River, ate at a lunch buffet at a superb Indian restaurant called Indian Garden near the corner of Fairbanks and Ontario, and took a break from sightseeing to watch the Cubs beat the Mets on the big screen in the hotel room. Then Kyle, my squeeze, and I caught a cab to Greek Town for dinner at the incredible Greek Islands restaurant on Halsted Street.  I should also mention that when we go out in Orlando with friends for dinner, splitting the check is a common occurrence, not so much in Chicago.  I asked a waitress in Chicago to split a check once and was promptly told that they don’t do that. My buddy confirmed that that is in fact usually the case in the Windy City, so be prepared to split the check yourself.

To top off the trip, we all went to the Sears … I mean, Willis Tower … at night.  My only regret is not doing this during the day. It’s very dark on the building’s Sky Deck at night and there are no attendants watching the capacity of the new attraction which I found odd.  When I first went to step out onto the Sky Deck’s glass balcony, a fellow tourist who was already standing there said, “Wait a minute, I think we’ve reached maximum capacity,” and then smiled. Nonetheless, walking on the new glass balconies was worth it and gives me reason No.103 to go back to Chicago (which incidentally is how many stories high the Sky Deck is).  There were three balconies open during my visit and it looked like a fourth was under construction.  I can’t wait to get back to Chicago! Hopefully, before next summer though I hear the winter is brutal. Thanks for the tip Kyle!