4 Days in Chicago with Kids

We took a trip to Chicago over Columbus Day weekend. It was supposed to be for the Chicago marathon. I’ve always wanted to run a major marathon so this was my 40th birthday present to myself. I signed up. We booked the flights. Found a hotel room in The Loop. We were on top of this. 

Unfortunately, my 40 year old knee had other plans.

I haven’t run since June. I did not run the Chicago marathon. It was a little tough. The entire weekend was geared around running. Everywhere you looked you saw people running or getting ready to run. The entire plane was packed with runners and runners talking about running. 

On the other hand, we had a great family trip and did a lot of things we probably would not have been able to do if I had run the race. Unlike Boston, Philly, NYC or D.C., which we’ve visited multiple times and can be more selective, we grabbed a CityPass and went straight tourist. 



We flew Spirit. Given all the stories you hear, we were a little worried, but it worked out great. It was a quick trip, so we had little luggage. And the flight was short so the girls didn’t miss not having in-seat TVs.

The planes were new, the flight attendants were funny. We really had no complaints. It was basically like flying SouthWest. We might have noticed all the extra tack-on fees for a longer flight/trip, but for a quick jump, I’d definitely fly them again. I never fit in the seats anyway.

By the time we fought through rush hour traffic and checked into the hotel, it was dinner time. After having sat on a plane and then in a cab, we wanted to walk (and wear out the kids) so we walked over to Revival Food Hall. It was a little longer walk than the kids would have liked, but once we made it, it turned out to be a great choice. 

The blue fountain (for the Cubs game) gave them just enough of a boost to get them the last quarter mile.


The food hall (basically an upscale food court) featured 15 fast-casual stalls with a variety of different foods from a bunch of different Chicago neighborhoods. This allowed us to hit up both some different food and different neighborhoods without actually having to get to those neighborhoods. 

Now, ideally we would get to visit all the distinct parts of the city, but we had limited time and 2 kids, so this worked out really well. So well, that we would come back on Monday to hit up a few more places.


After sampling some tacos (turned out it was too spicy for Ally), both Michelle and I opted for big bowls of ramen from The Furious Spoon. Cecilia went with a square of Detroit pizza from Union Squared. That turned out to be a very good choice and started my new obsession with Detroit pizza. We were all so hungry, we ate before we could get any photos of the food. That’s the benchmark in how good the food really is anymore, right?

The walk back was looming, so we shamelessly bribed the kids with a stop at Dylan’s Candy Bar to make their legs work. It worked.


We were staying at the Cambria hotel off Michigan Avenue. If I had to do it over again, I’d probably look for something closer to the marathon start/finish. It didn’t look far on the map, but I think it might have been a rough walk (ok, hobble) back to the room after the race.

The hotel was fine. They upgraded us to a larger room, so the girls had their own separate space  with a sofa bed. The extra space and additional TV worked out well as we were usually so tired from walking around all day that we were back in the room no later than 7.



We started the day be walking a few blocks from the hotel to Yolk, a small breakfast chain, that, given the line outside must have been giving it away or been really good. The girls couldn’t have been happier to discover S’mores pancakes on the menu. They had a new favorite restaurant.


After breakfast we took a free shuttle and checked out the race expo. I might not ever wear the shirt, but I had paid the entrance fee and was going to get some swag. The expo was big and efficiently organized, but really no different than many other race expos I’ve been to except in scale. We spent a little time wandering around, letting the girls get samples, then headed back into the city (the expo was a bit outside the city proper). 



We decided to get a CityPass and it turned out to be a great decision. A CityPass gives you discounted, and in some cases expedited entry, to your choice of 5 (out of 7) big attractions. It saved us money, avoided some lines and gave us a rough itinerary for our long weekend.

The first attraction we hit up was the Shedd Aquarium. We were impressed by almost all the museums and attractions we visited in Chicago, but the Shedd might have been at the top of the list. Maybe it just shone in comparison to the New England Aquarium which is dark and cramped, but the She’d felt big, open, bright and modern.

We spent about 3 hours wandering around inside and probably could have stayed longer. The girls loved the dolphin show and petting the sting rays.

It had been raining when we arrived on Friday and was mostly overcast on Saturday, but by mid-afternoon it was looking like more rain was coming. We decided to take a water taxi over to Navy Pier.


You’d think Ally would have had enough of Ferris wheels, but both girls were keen to go on the Centennial Wheel. As the rain and wind picked up, I was less than keen. But the weather definitely kept the lines down and I didn’t freak out too much in the large enclosed cars.

After the Wheel, the rain really started coming down and by necessity we discovered the usefulness of Chicago’s buses. We would become avid users over the next few days of the CTA. We did catch a rainbow when the rain finally let up.

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Damp and tired from a day of walking and touristing, we decided on takeout deep dish from a nearby Giordano’s for dinner. Given the influx of visitors and weather, takeout was a great decision. The pie itself was a little heavy for our taste. Just so much cheese and a rich crust. The girls probably liked it more than us, but we were glad we tried it, but still, Detroit-style was the clear winner from the trip. 



Another regret of not being able to run, was not being able to use the VIP tent tickets I had splurged on. Well, we still used them, but we didn’t get nearly the benefits we would have as a runner (massage, changing rooms, corral access, etc), but we did take advantage of the free breakfast and great finishing line seats. We even got to give Galen Rupp a high five.


After watching the leaders finish, we walked over and hit up the Fields Museum. This was probably the biggest disappointment. It’s a beautiful building, filled with a lot of interesting artifacts, but much of it feels very dated, especially in comparison to how some of the other museums we visited were set up and presented. 

There wasn’t a lot to really engage the kids. It was partly their specific interests (they are not into dinosaurs or natural history yet) but other than the Native American exhibit, I didn’t find that much intriguing either and I do have some interest in history. The staid and dusty dioramas just didn’t do it for me.

If we ever get back, the girls would be happy to re-visit all of the museums except this one. Knowing what we know now, we  likely would have opted for the zoo instead.

The Adler Planetarium on the other hand, was great. Set up for both kids and adults with interactive and informative presentations for kids and adults. The girls loved the Planet Explorers section (astronaut bathrooms provoked some interesting questions), while I really liked the Mission Moon exhibit recounting Captain James Lovell (Tom Hanks in Apollo 13) experience with the space program.

After exploring both museums, we opted for an early dinner at Acanto close by and right off Grant Park. Despite, or maybe because of, all the positive reviews, we expected to like this place more. We had an early reservation but service was slow. The food was good when it came, but relatively pricey. I think all of us were happier at the food court!

With two days of walking and exploring under our belt, with one more full day to go, we headed back to the hotel for an early night. We actually tried to hit up a sunset viewing at 360 Chicago (Hancock Tower), but so was the rest of the city. We took one look at the line wrapping around the block and turned around. We needed rested kids to survive another day of museums.



Our last full day and we had two big objectives on the agenda. Get to the top of the Hancock Tower and hit up the Museum of Science. 

After visiting Yolk again (this time for Oreo pancakes!), we hustled over to the Hancock Tower. Even 30-ish minutes early, there was a good sized line, but here is where the CityPass’s expedited entry really helped. Michelle and the girls went up in the first elevator and had the views all to themselves for a good 10 minutes before the next group arrived. 

(I stayed safely on the ground where my very active imagination and fear of heights could be held in check.)


Hitting up one of our big objectives before 10 a.m., we splurged on a cab and headed to the Museum of Science and Industry. This is the one big museum that is not close to any of the other ones. It’s actually in the one remaining World’s Fair building near the University of Chicago, a solid 20 minutes outside of The Loop. A cab was a good call.

Again, we were very impressed with the museum and probably could have spent more time there if we had the energy. As it was, we covered a good chunk of the sprawling building and the girls were very active and engaged the whole time with a variety of exhibits. This was Cecilia’s favorite.

The other big benefit of the CityPass is that aside from the expedited entry and general admission, it typically offered a movie and entry to one of the special exhibits. We wore some funky glasses at each museum.


For the MSI, we chose the robotics exhibit and everyone enjoyed it. Many of the exhibits were STEM activities aimed at kids, but don’t think I didn’t enjoy many of them.

After the robots, the weather demonstrations were the big winner. Who doesn’t love standing in a simulated hurricane.

The less said about the strange circus exhibit hall, the better. Though Ally did like being the “big” sister for once.


With all of our CityPass tickets used, we headed back to Grant Park and let the kids run around in Daley Park, which is a renovated corner of Grant Park and is basically a giant playground on steroids with climbing areas, bridges, sculptures, slides, lighthouses and an enchanted forest. And plenty of benches and grass for parents to zen out with views of the skyline.

We also got the requisite shots at Cloud Gate. Do you think Ally has had enough?

Finally, for our last meal, we headed back to Revival Food Hall, to hit up more stands and take advantage of their daily happy hour specials. This time we opted for the poke bowls, margaritas and some gelato. We walked back to the hotel full and happy.


We flew home.

Of all the big cities we’ve visited, Chicago reminds us most of Boston and despite not being able to run the marathon, we all enjoyed our quick trip and look forward to going back again some time in the future.

Maybe for my 50th birthday the girls will run the race with me!



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