Like any great destination, Chicago has so much to explore that a visitor could potentially spend weeks there and still not see everything. However, on a quick trip to Chicago last July, we didn’t have the luxury of having weeks to explore. In fact, we had slightly less than three days.
So how much can one possibly fit into less than three days in Chicago?
Quite a lot, it turns out, although admittedly, we barely scratched the surface of possibilities. We arrived on a Thursday afternoon, checked into our hotel on Adams St., grabbed lunch, walked to Willis Tower, (Willis Tower is the building formerly known as the Sears Tower, and in my heart, it will always be the Sears Tower). We bought a CityPASS and rode the elevator 103 floors to the top, and onto the Ledge of the Skydeck, glass floor balconies.
Thursday evening, we walked to the Chase Auditorium for the primary purpose of our visit, the taping of Wait, Wait...Don’t Tell Me, the NPR news quiz. If you enjoy listening to the show on NPR, experiencing it live is even better, and the audience gets a longer version before it's edited for time.
Friday, we attempted to go to a Cubs game, but as luck would have it, that was the day Chicago's drought broke, so instead of watching baseball, we got to experience a memorable adventure of a storm at Wrigley Field. Eventually, we gave up and took the train back to the hotel for dry clothes and opted for a double decker bus tour with stops at the Navy Pier and the Hancock Observatory. As we walked back to our hotel, we even got the chance to hear some live music at a free concert in the park.
Saturday morning, we made a beeline for the Shedd Aquarium to be there when they opened, and spent a couple of hours exploring the aquarium and taking in a dolphin show. We spent a couple hours in the Field Museum, focusing our limited time on the dinosaur exhibit and the totem poles. We had the chance to see some other parts of the museum, but only briefly, before moving on to the Art Institute, where most of our time was spent gaping at Monet’s paintings, with a nod to Van Gogh, some Asian art and the Chagall stained glass window. Saturday evening after a brief nap, we headed to the Kingston Mines for some fantastic live blues by Joanna Conner, who has been singing and playing guitar at Kingston Mines for years.
If you only have a short time in Chicago, you can still have an amazing trip. A caveat is that I would definitely not recommend trying to squeeze this much into a trip with small children. Also, it would be easy to spend at least one whole day at the Art Institute, the Shedd Aquarium, or the Field Museum, so if you’re short on time, consider looking at the map of each place and deciding ahead of time what your must-see exhibits are.
Tips for planning a great quick trip to Chicago:
- Pick a place to stay that's centrally located to the things you want to do and see while you're in town.
- You could rent a car, but dealing with driving in the city and trying to find parking makes public transportation a much better option.
- A CityPASS is a great value if you're planning to go to more than one of these places: the Shedd Aquarium, Willis Tower, the Field Museum, Adler Planetarium or the Art Institute, the the John Hancock Observatory or the Museum of Science and Industry. The pass offers admission, usually without waiting in long lines. You do have to choose between the Art Institute and the Adler Planetarium, and between the John Hancock Observatory or the Museum of Science and Industry. The pass is good for nine days starting the day you first use it.
- The double decker bus tours are also great because you get a guided tour of the city that allows you to get off the bus and explore at a number of different points of interest and then hop back on the next bus and continue the tour. You can get tickets for the bus tours in various locations, including across the street from the Art Institute.
- Bring snacks and water.
- Wear comfortable shoes.
- If you want to go to a taping of Wait, Wait...Don't Tell Me, you'll need to plan ahead. Currently, shows through the end of February are sold out. Tickets go on sale about six weeks ahead of time, and they sell out quickly. Tickets for March 7 and March 14 go on sale February 1.
- Some people like cold weather, but personally, I would plan my trip to Chicago for May or later so that it's warm and the Cubs will be playing.