Chicago: the 5 hour Windy City highlights

Every year, the University puts together a bus to take students to Chicago for a day. (The students have about 5 hours in Chicago before the 5 hour drive back to Ohio). It is free of charge for the first 100 students who sign up. I managed to sweet talk my  way into a spot, only to find out that I was to be “in charge” of the bus I was on! So much for a “free trip!” 

I’m not particularly fond of big cities and wasn’t exactly sure what to expect. I did like the fact that there seemed to be lots to do, and went on the trip figuring it would be a one time “see Chicago and done” sorta thing. 

I offered an extra credit assignment to my students: put together an day’s itinerary for Chicago. I’ll pick a winner and follow their itinerary. The winner:  Free walking tour via Chicago Greeter’s program, Art Institute, Millenium Park, and then just walk around the city.

The Chicago Greeter’s program ( is a great program put together by the city of Chicago. You can sign up and volunteers will take you on guided 1-4hr tours of Chicago. Unfortunately, the Greeter program is only if you are in Chicago for more than 1 day, so I was steered to the “Instagreeter”. Upon arrival at the Cultural Center, the next tour was an hour wait and given the time constraints I knew it wouldn’t work.

Of the itinerary, I attempted the Greeter’s program, did see Millenium Park, and walked all over the city! The Art Institute was a bust, again mainly due to time constraints.

Trip highlights:

Millenium Park and “the Bean”, Navy Pier & Michigan Ave.

Most of the day was spent walking around, but I did utilize the public transportation (bus) and found it super easy to use. The bus drivers were very helpful and easy to deal with. (Although one lady was a little scary at the get-go, she warmed up and was really nice to me and my travel buddies.  All the “yes ma’ms” may have helped our cause!)

Missed the mark at Navy Pier, as we didn’t go inside but now something to add to the list for next time! There was an impromptu stop to check out the Park Hyatt Chicago, complete with a trip to the 7th floor to see the restaurant. Swanky!

I really enjoyed walking around and taking in the sights. The buildings (keep an eye out for historical markers on the side of the buildings!), the street performers, the fashion on Michigan Ave, and the people out walking their dogs.

Doh! Moment

I really wanted to see the Tribune Tower – Apparently I walked right by and didn’t realize that I had – I was very dissappointed, especially since I didn’t have enough time to walk back and “see” it! Another next time!

Food highlights –

I decided I wanted to eat somewhere that was not the “norm”. I went with a spot called “Big & Littles” that was featured on Diners, Drive-ins, and Dives. It was only a half-mile walk from where the bus dropped us off. Menu items include po’boys, fois gras, truffle fries, burgers, and more. It is a cash only spot and opens at 12pm on Saturday. I got there at just a touch before noon but the joint was open for business. The timing on my part was perfect because not too long after there was a line forming! I ordered a pork-belly po’boy and truffle fries. It was yummy!! Pricing isn’t cheap but it was definitely a treat!

The second eatery was Gino’s East. This famous Chicago spot was only 3 min from the bus pick-up location, so a good choice for the “dinner meal”.  We ordered a small cheese Chicago-style pizza and it was plenty filling! (Pizza’s do take about 45-60min to bake, so allow for plenty of time!) The small was plenty for the three of us but I think I still prefer NY style pizza.

Ending thoughts –

I was pleasantly surprised by Chicago. I found it to be clean, pedestrian friendly, and easy to navigate. There is so much to do that 5 hours just isn’t anywhere near enough time. There is something for every taste: museums, zoo, aquarium, shopping, food spots, art galleries, pubs, and history. I see myself going back in the spring or summer for a long weekend.