My family and I just spent a quick two days in Chicago and had a blast! I've already had two friends reach out who have plans to go there soon and wanted to hear what our suggestions would be. Of course there are a ton of fun things to do and see in Chicago, but here were the hits for our us and our teens.
Chicago Cubs game obviously. This was the reason behind our trip and the highlight for sure. Wrigleyville is just such a blast- what an atmosphere! We headed there EARLY as we wanted to make sure we had time to take it all in. We bought all street merch we could- hats, t-shirts, pennants, more hats, and of course peanuts and waters to take into the game. We made posters, saw the Budweiser Clydesdales and drank one or two Old Styles at The Cubby Bear and Bernie's Tap and Grill.
Then we headed into our seats, which we had pre-purchased our tickets just a couple days prior from Craigslist of all places. We had heard, correctly, that season ticket holders will advertise tickets they aren't using there and while we didn't get a smokin' deal on them, we didn't have to pay any of the service fees through the normal ticket outlets, which ended up saving us around $100 (and took care of all of those souvenir items and Old Styles). Plus we had pretty great seats. As tradition would have it, we had a couple of Chicago dogs, which if you haven't had one, sounds kinda gross, but is kinda awesome (an all beef dog in a poppy seed bun topped with yellow mustard, sweet relish, freaking tomato slices, diced onions, kosher pickle-spear, sport peppers and celery salt). Kinda makes my mouth water just reading that now! We were lucky to get the full Cubbie experience with an opposing team "throw it back" home run for their only score and the Cubs flying the "W" flag at the end of the game with a 10-1 win in gorgeous weather! Hard to beat.
The next no-brainer on a trip to Chicago (especially with teens) was indulging in their famous Chicago Deep Dish pizza. We took it a step further by making our own contest out of trying two of their most famous establishments so we could form our own opinion on this highly contested topic. Lou Malnati's vs. Giordano's. (Remember we were only there for two days, so yes, we hit up deep dish pizza once a day and we have no regrets.) I put it up for debate on my social media and was floored by how straight down the middle the responses were on which one is the presiding favorite pie. For us, it was an unanimous Lou's (although some of us were more passionate about our choice than others). I now understand the great controversy and devotion to one's choice (my friend described one of them to me as "garbage"). For me personally, that flaky, buttery crust of Lou's topping their sausage patty and ooey-gooey cheese with that fresh tomato sauce, just had me at first bite. A fun one to decide for yourselves. I would recommend eating at off times or joining a waitlist. There is a reason everyone wants to eat at these places, so give yourself plenty of time.
I also love Millennium Park and goofing off at The Bean. Just people watching and taking funny Bean pictures and seeing the skyline behind it is quintessential Chicago to me. I could also spend an embarrassing amount of time watching the Crown Fountain and it's faces changing and guessing when the water will shoot out of their mouths. Also an excellent place to cool off! We stayed further down in the Grant Park area and it worked out perfectly to grab a coffee and walk to Millennium Park. It was odd though, when we walked out of our hotel it sounded like a massive swarm of insects was overhead only to find out it was the NASCAR Street Race, unknowingly happening right outside our doors. So...what was meant to be a nice, quiet morning walk through the park, ended up being interesting in other ways. I love that about a big city though, you never know what you'll be experiencing! Also check out their website to see what events are happening in Millennium Park when you are in town. Great option for an outdoor concert, movie or other event.
Grant Park at night
We then cooled down in The Art Institute of Chicago. It wasn't my first choice with the boys, I was hoping to hit up the Museum of Science and Industry, but it was fun going through the different exhibits, especially the modern art section and wondering how on earth some of the exhibits were museum worthy! Of course Chicago is famous for their great museums and has tons to choose from.
We hadn't planned on it, but we had a birthday boy wanting some new "dunks" so we hit up the Nike Store on The Magnificent Mile on Michigan Avenue. My three boys aren't into shopping, but the younger ones liked Nike and Garrett's Popcorn (but if you're bringing some home you might wait to get it at the airport instead of carting it around all day) and the older one liked the Starbucks Reserve Chicago Roastery which if you haven't been to one, is a unique place to stop of a treat. I love how walkable all of this fun stuff is! An easy and fun walk over the Chicago River from Millennium Park. I would've loved to spend more time along the Chicago Riverwalk, or even take the kiddos on the popular Architecture River Boat Tour (there are a few to choose from), but time didn't allow on this trip.
Another major trip highlight that I heard about through a friend who was a Chicago native and involved in the comedy scene, was Second City's version of an all ages show. For those that don't know, Second City is the famous improv comedy troupe which has been the starting point for so many well-known comedians, especially those that are on Saturday Night Live. So...if you are there without the kids, for sure hit up one of their shows, and if you are there with your kids, hit up this all age appropriate show called ComedySportz Chicago. All four of us thought it was hilarious and were beyond impressed with their improv skills. Totally unique, fun, family night. Also, the neighborhood it is in, Old Town, is adorable and had lots of great looking restaurants, so maybe grab a ressie or make a plan to really spend some time there.
Finally, you must hit up a great Chicago steak dinner. I'm not sure we picked the city's best place because I went just by location to our hotel, and although it was good, it wasn't mind blowing good, so do your own research here. I do know from past experience that you can't go wrong at Gibsons.
It's also worth mentioning that my public transit loving husband had us take the train for our entire trip (as he does everywhere we go) including to and from the airport (which was money during a massive rain storm). As one of the only cities in the U.S. who make public transport easy and convenient to use, I think it is well worth getting off the Uber train and giving the train a go on your trip. The 'L' train is easy to navigate, inexpensive and a great opportunity to teach the kids about the importance of utilizing public transportation for our planet as well as read maps and help navigate the city. Our excitement built as we got closer and closer to Wriggly weeing all the Cubs fans piling on, and there was only one time late at night that I didn't feel totally 100% comfortable (and it was our stop of all places- Roosevelt on the Red Line), but there were a lot of cops there. Anyway, I might not be selling it, but would urge you to give a try at least once on your trip. It is a Chicago experience in its own right!
Other spots that were on my list, but didn't make the cut this trip are listed below.
Blue Man Group or other show
Comment below on what tops your list of must-see and dos in Chicago. I'd love to hear!
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