Our family took a long weekend vacation to Chicago over Thanksgiving. The girls were about to turn two, so we wanted to take advantage of one last flight without having to buy seperate tickets. We searched for flight deals from Knoxville and found cheap flights to Chicago. Growing up in Indiana with Chicago right next door, it wasn’t really on my radar as a travel destination, but I am so glad I gave Chicago a second look! Chicago has a lot of things to see and do, especially with kids and also when it’s cold outside.
We did Priceline Express Deals so flight times were luck of the draw. We ended up with a really early departure on Sunday, so our four-day trip really was more like a three-day (2 1/2 days) trip. Here is what we packed into our short time in Chicago.
Day One
This was our short day as our flight arrived midday. It also happened to be Thanksgiving. We took the CTA Blue Line into the city from O’Hare. We made a short pitstop at the “California” station to see the Greetings from Chicago mural. The mural is about two blocks from the station and is a great photo stop on your way into the city.
Once we got into the city, we dropped our stuff off at the hotel and headed straight to the Willis Tower. The sun sets about 4:30 pm this time of year (late fall) in Chicago, so our plan was to arrive at the top around 4:00 pm and see the city in both daylight and at night. Unfortunately I just purchased general admission tickets in advance because I thought the tower wouldn’t be busy on Thanksgiving. Words of advice: buy the fast pass ahead of time no matter when you plan to visit! Oddly, the tower was packed on Thanksgiving. We had to wait for two hours to get on the elevator to the top, and it was already dark. The fastpass line was 15 minutes. I was also disappointed to discover once we got to the top that there was a line to see the ledge, which was another hour and a half wait. Needless to say, we chose to skip this feature. All in all our trip to the Willis Tower was disappointing, but I think it would have been better if we had purchased a fast pass and not gone on a holiday.
That evening we ate deep dish pizza for dinner at Giordano’s. It was delicious!
Afterwards we took a stroll down the Magnificent Mile, which was lit up with Christmas lights.
Day Two
We started our day off at Millennium Park to see Cloud Gate (“The Bean”) and the Crown Fountain (wasn’t on). We also stopped across at the Cultural Center to see the Tiffany Dome. The Cultural Center isn’t a hit with the kiddos but it was just a short stop for Mama and Daddy to marvel at the architecture. What is a hit with the kiddos is Maggie Daley Park, which is right next to Millennium Park. Maggie Daley Park has a very large and creative playground area that our toddlers loved. They also turn the roller skating track into an ice skating rink/track for the holidays. We would have loved to have done this if the girls were just a little bit older. With all of these sights, Millennium Park took up our entire morning.
We breaked for lunch at Shake Shack (a family favorite), which is right next to Millennium Park.
After that we headed off to the Field Museum. The Field Museum is a natural history museum. It is a little advanced for toddlers, but I snuck it in more for myself with hopes they would nap there. They do have an extremely large taxidermy (I think they are taxidermy) animal collection, which our animal loving toddlers did enjoy.
Next we went to the Museum of Science and Industry. This museum is totally geared towards children and was a big hit with our toddlers (and my husband). They have a Boeing 727 suspended on the third floor. They have other examples of planes, trains and automobiles. They also have a huge model train setup. They have a section on farming that includes a tractor and combine. They have hatching chicks in a section on genetics. They also have a weather area that includes a floor-to-ceiling tornado. Because of the holidays, we also got to enjoy a Christmas Around the World exhibit with 50 Christmas trees decorated for different countries. You can use the Metra train from Millenium Park down to the “55th-56th-57th” stop to get to this museum, which is in the Hyde Park / University of Chicago area of Chicago (a little ways south of downtown).
Day Three
We started the day off with a photography stop for Mama at Wells Kinzie Parking Garage. The parking garage is a couple of blocks off the Riverwalk. It’s 7th floor cutouts are a great place to peak out over the El. The girls actually enjoyed this stop and kept asking for more trains to go by.
Next we headed over to the Riverwalk and walked from there down to Navy Pier. I was impressed that our girls walked the whole way themselves. That being the case, this walk took us about an hour.
At Navy Pier, we went up in the ferris wheel. This ended up being one of the girls’ favorite things. They squealed with delight and ran around the gondola. The other outdoor attractions were closed for the season, but Navy Pier does have an indoor Winterfest that starts at the end of November (we were a weekend early).
After Navy Pier, we headed up to Lincoln Park to spend the rest of the day. We first trekked over to Fullerton and Lakefront Trail to get some views of the city (you can also stop at North Ave Beach, but we decided to steer clear of the sand).
Next we went to the Peggy Notebaert Nature Museum. This a small, inexpensive museum that is great for children. It has a water play area, lots of live reptiles and amphibians, a couple of indoor themed play areas and a butterfly garden. We arrived just in time for their daily butterfly release.
After that we took a stroll through the Lincoln Park Conservatory. The conservatory is free, small and a great place to warm up when it’s cold outside. It was a great way to kill some time while the girls napped in their carriers.
Our final stop of the day was at Lincoln Park Zoo. Lincoln Park Zoo is one of the oldest zoos in North America and is one of the few ones that is free. It reminded me of zoos you see featured in children’s books with a very open, park like feel. It also has a lot of indoor exhibits, which are good for cold weather (the girls really enjoyed the gorillas). The zoo also had extended hours and “Zoo Lights” set up for the holiday. It was the perfect way to extend our day a little into the night.
Additional Day
If our flight had left later on Sunday, and we would have had additional time in Chicago, here are a few changes I would have made to pack a few more kid-friendly sights to our trip. I would have moved all of the Lincoln Park sightseeing to Sunday, so we would have been at Navy Pier midday Saturday with an open afternoon. I would have added on the Chicago Children’s Museum, which is at Navy Pier. After that, we would gone up in the John Hancock building, which is another tall observatory near Navy Pier (I am a sucker for city views).
If there had been enough time either on Saturday or Sunday, the last place on my wishlist would have been the Shedd Aquarium. If we had been able to add on these items, I would have purchased the City Pass to save some money. Because of the timing and what we were able to see, it was cheaper for me to purchase tickets a-la-carte.
Chicago was a great short sightseeing trip for us. I think we managed to see a lot, but also leave enough to warrant a return visit. The girls were a little trickier to manage than when we went to Norway a couple of months ago. They are bigger too, and we ended up renting strollers at the museums to ease the burden of carrying them (because they didn’t want to walk as much as we expected). Naps on the go were way shorter than we hoped, which made for tricky evening activities. I always remind myself in these moments that we are pushing their limits and to give them grace. I also try to find ways to redirect everyone in a positive direction (such as a snack pick me up) and focus on the positives. Even though there were trying moments, the girls got to see a lot of interesting things (they are still obsessed with pointing out busses), and for that I am very grateful!
To this day, the girls still talk about Chicago. They like to pretend play they are going to Chicago and tell us every airplane is headed there.