36 hours in Chicago just isn’t enough. This city has so much to see and explore that it deserves a longer stay to fully experience it. If, however, you only have a weekend in the Windy City like I recently did while visiting for the marathon, you can get a pretty good sense of at least the famous landmarks and sights. Exploring the downtown, walking along the water, grabbing a deep dish pizza, perking up with some coffee, and familiarizing one self with the local craft beer scene hits the top of the Chicago checklist. And everyone needs at least one Chicago hot dog to say they’ve actually lived.
We’ve found that traveling with twin toddlers, it can be difficult to find a space that actually works for us to stay. We’ve come to realize that a single room doesn’t work well for us as the boys don’t sleep well if they are distracted by our presence. Instead, we’ve found great places to stay, typically homes, from AirBNB and VRBO. In Chicago, we find a fantastic historical home about 20 minutes from the city (except during the terrible rush hour) that worked great for our stay. The boys sleep in a separate room thanks to two pack and plays we bring as we stay downstairs and enjoy the TV with each night. We probably could have even brought the dog.
On the first night in town, we arrive late, close to the boys’ bed time because of our long road trip. Instead of scrambling for food and prolonging their bedtime, we get them to bed and then utilize our host’s suggestion of using Uber Eats to get delivery from a nearby brewery he recommended, Open Outcry Brewing. While I would much rather visit the brewery in person, the boys are asleep and I run the marathon in two days, so don’t want to drink. For a brewery they bake up a pretty good pizza. We go with the spicy meat pie and the buffalo chicken. Can you tell we’re fans of spicy food? Though not deep dish, these pizzas show us that Chicago can make good regular pizza too.
The next day we focus on exploring Chicago’s downtown. We find parking easily thanks to Chicago’s integration with SpotHero, an app that allows you to reserve spots in garages, pay for street parking without a meter, and save by reserving ahead of time. Thanks to the app not only are we able to get a great spot right by Millennium Park today, but we are also able to park right at the start gate, skirting a ton of traffic on the day of the marathon.
We begin at Millennium park, but quickly find we are in need of some coffee and food to fuel our adventure. Nearby is a highly rated bakery and coffee shop, Goddess and the Baker. Because of the marathon, tons of very athletic looking people are crowding the store and lined up our the door. The line moves fairly fast, though it takes longer for the coffee to be made than the breakfast sandwiches. I accidentally grab someone else’s coffee before heading out and and horrified at what I’ve waited for, a cloyingly sweet drink while my wife’s latte is ice cold. Thankfully we straighten out the orders and actually get ours which are pretty good. The breakfast sandwiches are awesome, though we can barely enjoy them as we get swarmed by big fuzzy bees near the park whenever we open them up. What’s up with Chicago’s giant bees?
We take our coffee to go and begin exploring Millennium Park again, this time discovering the massive reflective metal structure known as the bean. I’m surprised to find it much larger than I expected. The boys absolutely love seeing their reflections in the massive mirrored surface and get a kick out of walking up and trying to grab it. They also enjoy going underneath the curved middle of it.
From the bean, we head over to the water of Lake Michigan. The park connects to the Lakeside Trail, winding along the shore past a marina, ferries, and tons of kayaks. We cross a traffic bridge running over the Chicago River, the famous one in a lot of pictures and that gets died green for St. Patrick’s Day. I feel like there was a Vince Vaughn movie where he drove one of the tourist boats here. Though we don’t take the tour, we stop by a boat to show the boys and the skipper is nice enough to give them little boat captain hats. People in Chicago constantly surprise us with their friendliness, probably because we are cold hearted East-Costers.
We come to the Navy Pier, a massive pier jutting out into the lake from the shore. The pier houses a museum, several restaurants, a small amusement park, a few bars, and even a beer garden at the end. At the very tip the full power of the wind in the Windy City is felt coming off of the lake without any buffer. I love the atmosphere at the beer garden as well as the drinks people can carry around the pier, but again choose not to partake. I hope to come back soon.
From the pier we head back toward town, following the river to the Miracle Mile, a wide boulevard that runs through the downtown housing a ton of shops, many high end. It’s Chicago’s version of 5th Avenue or the Champs Elysees. A favorite is the multi floored Nike store, featuring not one but two live DJs and a ton of marathon gear. Also along the street is a sports radio station broadcasting live. A few plazas provide nice spots to stop and rest our weary feet. Crossing the river provides some great views of the city perched over the river.
We make our way back to the car via downtown and a quick meander back through the park. With weary legs, we decide to take a short driving tour north of the city along the shore. We head up the Lake Shore Drive, passing Chicago’s large public beach. We also drive through the campuses of Loyola and Northwestern. I decide I prefer the historic grandeur of East Coast college campuses and don’t love the modernity of Northwestern. Heading back toward town along the great lake’s waters, I’m struck by how much the lakes really feel like the ocean. Massive barges cruise slowly in the distance and there is no trace of land over the horizon. I marveled at the same sense of scale when we visited Detroit earlier in the summer. A beach house along the shores of the lake might be fairly convincing.
Back toward town, we stop in at Pequod’s Pizza, one of the most famous destinations for deep dish or as they call it, pan pizza in the city most famous for it. A dive bar atmosphere pervades, but it manages not to feel seedy or gross. The inside is deceptively massive with multiple floors and rooms, so even though it gets packed, the wait time is only occasionally prolonged. The longer wait is for the pizza to actually be cooked, but we end up only waiting maybe 20 minutes even though we’re told it will be 40. There’s even beer available from some of the local craft breweries and not just the big domestics as you’d expect at a dive. The deep dish is succulent and doughy. Each slice requires diving in and indulging in a monstrous bite. I love a good pepperoni and this pan pizza has a good pepperoni.
All good pepperoni must come to an end, and we head back to the house, our boys full of pizza. If my childhood was any indication, this is just the first of many, many pizzas they’ll consume. We head to bed early in preparation for an early start at the marathon in the morning. Thankfully, with our close location and parking prep, I arrive quickly with plenty of time. Because of the deep dish, I am well fueled for the run as well.
After the race, we attempt to get in at Au Cheval, a tiny dive counter burger bar many consider the best burger in the country. Like Shake Shack, they’re quickly expanding and attempting to build a premium burger empire. With all of the marathoners thinking along similar lines, the wait exceed three hours. Instead of waiting it out at the nearby gastropub which is admittedly enticing, we head further out of town to Revolution Brewing. This brewpub is a fairly established mainstay in Chicago but has a modern design and atmosphere. Even this far out, many runners have the same idea and the wait is a bit longer than normal. At least it gives us time to sample a few of the extensive list of beers they have on tap, brewed here. I particularly enjoy the Oktoberfest brew since it is the season after all, as well as an American Pale Ale, the style I always find tastes best after a long run. It must be the electrolytes in the hops or something. Science!
We hang out for a long time at the brewpub, enjoying some incredible fries that the boys mostly steal from me, and massive burgers that I can barely finish. The beer, however, I do finish. We head back to the house again for a good night’s sleep before the long drive home the next day.
Chicago is packed with way more incredible restaurants and sights than anyone can see even with a much longer stay. There are so many fantastic places to see and things to do that a vacation could last weeks here. When there’s only a little time to make the most of it though, having a plan to strategize seeing the major sights and experience the best of Chicago can mean the difference between seeing it all and missing it all. The city spreads out pretty far, but focusing on the downtown area and driving to spots that are fairly close helps to see the most. The Windy City is definitely worth a visit!