Eric's Trip to Chicago

The opportunity to go to Chicago came up in conjunction with a family reunion in Ft. Wayne, IN on Sept 8, 2007. We decided to take advantage of our time in the Mid West by flying out a few days early to visit Chicago from Sept 2 – Sept 5 to then drive down to Ft Wayne from Sept 6 – Sept 10 to spend time with Uncle Jim, my cousin Jamie along with a sh*tload of other cousins that I have not seen in 15+ years.

Unfortunately, Dee Dee is not able to join the trip for she’s saving vacation days for the trip to AU and NZ in Nov of this year. So cutting to the chase, this means 8 days solid of family, Family, FAMILY!

We took the EARLY flight out from San Jose to Chicago’s Midway airport on Southwest. The flight was only $215 roundtrip with flying out on the Sunday of Labor Day weekend and retuning the following Monday, Sept 10. The flight was quick. It really pays to fly on off days and off times to get the best rates! We booked 4 nights at the Hotel Monaco on Wabash Ave in the heart of the city…near the Wrigley Building. This is a great location because it’s really close to all the major sights. The hotel is a boutique with the hip flare to it…and does well with service too. I highly recommend staying here…or at any other Kimpton hotel (the parent company of the Monaco).

Our cab got us to the hotel at 1:30pm and then we walked down to Portillo’s Hot Dogs for a Chicago style hot dog…which means a beef frank, onions, tomatoes, jalapeno peppers…and a dill pickle included in a hotdog bun. Hmmm…good. I never new this was a hotdog combination that was indicative of Chicago. Portillo’s is famous for these hotdogs and the restaurant has a lot of Chicago history.


After lunch…burp…we cruised down to the Water Tower at the top of the Magnificent Mile (Michigan Ave).. There is not a lot to see there, but it was the only building that survived the great Chicago fire…so it was worth seeing. There is a GREAT church just North of the tower that reminded me of the European gothic cathedrals I’ve seen. We walked down Michigan and passed by all the high-end Park Ave, NYC - type stores and gazed up at the various buildings. Magnificent Mile is lined with world famous buildings that are know as architectural works of art…seriously; Sears Tower, Hancock Tower, the Tribune building, the Palm Olive Building and the Wrigley Building . We stopped on Michigan Ave near the Wrigley and sat on a bench to watch the people and to sketch the architecture close by. My Dad did some amazing quick sketch drawings…I doodled my “impressions” of the buildings as best I could. I really like drawing…it’s a great way to capture the surroundings beyond taking a picture.

We at dinner at Bella Bacino’s which was on Wacker St and had a Chicago style pizza. Very cheesy…very good. The best part of this restaurant is the VIEW. We sat at street level and had great evening views of Wrigley and the Tribune Towers. After dinner we went down to Millennium Park to check out some really great art installations after dark. A lot of people were strolling around…a jazz festival was winding up…fireworks were shot off. I am amazed that this park is so CLEAN…there was NO graffiti and the park is very clean. Wow, San Francisco could learn a few things from Chicago.

After dinner we walked down to Millennium Park to see the tail end of the free jazz concert. Millennium is great with really great art installations that are engaging for everyone…including a giant water sculpture and metallic “bean.” The park also has a concert area with theater seats and lawn area. If you visit Chicago, be sure to look up what’s happening at Millennium Park…chances are there is a free concert or performance.