My aunt and I made use of the September long weekend to check out Chicago. We found a flight as a great price flying from Detroit where we had to spend a night at a hotel near the airport both on our way to and from Chicago.
We had to spend quite some time to find a Chicago hotel offering good prices for a long weekend. Since we wanted to stay downtown, the Hotel Cass, a Holiday Inn Express hotel, was offering a better rate compared to the others we were considering and it also included breakfast. The hotel is located within walking distance of the Magnificent Mile and is in a quieter neighbourhood of the downtown area.
As our flight arrived in Chicago early Saturday morning, we had the opportunity to spend the full Saturday sightseeing. We decided to utilize the hop-on hop-off sightseeing bus to get around town. I had found the tickets online at Viator.com. Viator was offering a 3-day pass for approximately $33 per person which also included some neighbourhood tours. If we had bought the ticket from the hotel, it would have cost about $35 for only one day.
Residential Tower
Most of the information we found both for the things we did and for the bus tours we got through the Chicago Water Works Visitor Information Center and the Chicago Cultural Center Visitor Information Center . Both this information centres were easy to find and the staff were able to help us. Whilst you’re at the Cultural Center, make sure you go to the top floor to take a look at the Tiffany ceiling as its quite impressive and also used to be the public library.
Faces of Chicago Display
Residential Towers
Here are the things we did during our stay in Chicago:
1. Art Institute of Chicago
As with most large art galleries, you’ll need at least 1-hour to roam around. Even if you’re not into art, it’s worth going just to have look. In the pamphlet we picked up, it gives a list of the important pieces to see if you’re short on time. Otherwise, look around leisurely both at the art and at the interior of the building.
We decided on going to the Art Institute on the Sunday and noticed huge line ups for a day or so beforehand. There was a special Roy Liechtenstein Pop Art exhibit and the weekend we were in Chicago was the closing weekend. It would have been worthwhile to see if we weren’t deterred by the wait time to enter the special exhibit area. We spent maybe an hour waiting in line to get general admission tickets and found out once inside that it was another 45 minutes wait to enter the special exhibit
3. Navy Pier 
It was nice place to stroll especially at night when everything is lit up. It’s a great place to get views of the night Chicago skyline. We were told by the tour guides on the sightseeing bus that it’s the number 2 tourist attraction in the state of Illinois. It has a similar feel to the CNE where there’s not a whole lot to do except stroll and look around.
There is a great stain glass museum which is free. It was the highlight of the evening and of the Navy Pier. All sorts of stain glass windows, both modern and old styles, were on display. We also found where the Shakespeare theatre is and there was one other theatre which had an Asian performance on when we walked by.
This was a happy discovery during our stay in Chicago. I had seen the flyer in the cultural centre and asked the staff when and where it took place. Its dance lessons occurring every Thursday to Sunday with live music following. The dance series have been held for 16 years every summer. We checked out the dance lesson on Saturday evening. There was going to be flamenco music after the lesson but we would have had to wait half an hour so we left. The following evening was family lesson in swing dancing following immediately by a band playing swing music for the locals and visitors to practice what they learned. It was a neat experience to see.
4. Chicago Architecture Foundation (CAF)
The CAF has a whole list of walking tours to choose from which are conducted on separate days and times. They also do architectural boat tours several times a day.
We decided on doing the Historic Downtown (South loop): Rise of the Skyscraper walking tour. The starting and ending point was at the CAF. Our tour guide met us in the interior of the building and began by introducing us the building we were in and pointing out architectural features that were unique to Chicago. From there, we did the 2 hour walking tour around the south loop area, taking in the history of several buildings and why they were the way they were. We were able to admire the interior of a couple buildings. It was a good walking tour and would have been a good introduction as well to the city had we done one of these walking tours first.
Our tour provides an overview of historic and modern architectural styles, plus many stories about the people who designed and built our city. The Chicago Architecture Foundation has literally written the book about the Chicago River, so accept no substitutes!
Chicago Skyline from the Boat Tour
5. Neighbourhood Tours
The hop-on hop-off bus also offered neighbourhood tours as part of their pass. We checked out the tour going through Chinatown, Greek Town, and Little Italy. It was an ok tour even though we didn’t get off in any of the neighbourhoods the bus passed through. I was expecting more condensed area for each of the places we drove through. It was more suburban in feel than quaint neighbourhood compared to what I expected.
Throughout the weekend, the tour guides on the bus tours would always mention three main dishes to try while in Chicago – deep dish pizza, hot dogs, and steak sandwichs. We did try a pizza – it wasn’t deep dish, instead it was a thin crust pizza which was super delicious. It was next door to the Embassy Suites and was a short walk from the hotel we were staying in. We also tried a stead sandwich which was ok. Lastly, we had to try Rick Bayless’ restaurant, Frontera, while we were in town. Frontera serves Mexican food and the dishes we had were yummy – make sure you show up at the beginning of the lunch or dinner service to get a table. Reservations, we were told, are hard to come by as it’s a 6 to 8 week waiting list and there are only a few tables available for those of us who don’t plan weekend getaways that far in advance.
