For six months, Legend and I lived across the United States from each other. One of us traveled to visit the other as much as we could. We realized we could both get direct flights to Chicago on Southwest Airlines, so we used our miles and arranged to meet for a weekend there. It was the last time I saw Legend before he moved the United Kingdom (I joined him four months later.) I knew I’d be okay eating gluten free, but I was really hoping to get some pizza on our trip. Here’s how we did a weekend in gluten free Chicago.
Arriving and logistics:
We both arrived at Chicago Midway on a Friday night. It was cheaper to stay out by the airport, so we booked a hotel nearby. Each day, we took the shuttle back to the airport and then hopped on the ‘L’ train to get into the city. We bought Chicago Transit Authority Day Passes, which let us use the trains and buses as much as we needed. The trip from the airport to the city was about half an hour.
In hindsight, it would have been nice to have stayed closer to the city, but we opted to save quite a bit of money by staying near Midway and traveling each day. The train trip was extra-long when we were there because of construction on the tracks. About halfway to the city, we had to get off the train, board a bus, and take the bus to the next station before re-boarding the train. We figured out how to just get where we needed by bus, but it was inconvenient and wasted more precious time.
If you go, I’d suggest carefully weighing your options when it comes to where to stay!
Gluten free Chicago Day 1
After breakfast at the hotel, we caught the shuttle back to the airport, bought our day passes for the trains and buses, and boarded the ‘L’ train to the city. We managed to switch to a bus that took us directly to Navy Pier from the station where the construction works interrupted the train services. At Navy Pier, there’s a bit of a shopping center, an area with a nice view of Lake Michigan, and an amusement park. There’s also a couple theaters and lots of event space. There’s tons to do and see here.
We wandered around for a while before landing in the amusement park, where I discovered that Legend had never played mini-golf. Clearly this had to be remedied, and of course, he beat me. Twice. After walking around and playing a couple highly competitive golf games, we were ready for lunch. Legend wanted to go try the offerings from Chef Rick Bayless, who owns three Mexican restaurants in a single block in walking distance from Navy Pier. We started at Xoco, a quick-service café offering food and desserts in a casual environment. We opted to try the guacamole bar – tortilla chips with guacamole, choice of two toppings (like cheese, roasted poblano chiles or even bacon) and a side of salsa. It was pretty delightful. We then headed over to nearby Frontera Grill for lunch. After a lovely Mexican meal, we went back over to Xoco so Legend could try the churro with chocolate dip (sadly, not gluten free). Both Xoco and Frontera Grill were very helpful in identifying gluten free options for me so they are both good places to visit if you’re in the area.
That afternoon, we continued our wander around Navy Pier and the streets of Chicago. We headed over to check out Millennium Park to see the Cloud Gate Sculpture (that big silver bean thing). After all that walking and wandering, we were getting hungry. We stumbled across a Lou Malnati’s Pizzeria, but it was totally full. We found out there was another, larger restaurant in the Gold Coast neighborhood that we could get to by train, so we called ahead to try and reserve our place in line and headed across to the other location.
We had to wait for over an hour, even with calling ahead, to get a table on a busy Saturday night. Once we finally got a table, I was completely starving and grumpy. I ordered a small gluten free pizza and Legend opted for the deep dish. He was underwhelmed, but I loved mine. It was, at the time, the best gluten free pizza I’d ever had. (That honor now goes to my mom (Grandma T) for her homemade gluten free crust.) If you go, try to go when it’s not busy (if that’s even possible.)
Post-pizza we were pretty exhausted, so back on the ‘L’ we went to get back to our hotel. We were “treated” to a live performance on the train by an industrious man who sucked at rap. He just banged on stuff and yelled about God. It was so bad it was funny. No one seemed bothered by his performance, so I would guess that this kind of stuff happens all the time.
Gluten free Chicago day 2
We headed into town on a mission. Legend knew about some coffee place he wanted to try, so we headed back over to the area we’d been in the night before. This time, we explored Old Town, where we found some cool little shops and delis. I hadn’t eaten enough that morning so we stopped for an early lunch at a restaurant called Hash Browns, where I ate the worst hash browns of my life. I ended up going to Jimmy John’s not long after to get some real food. We also found the Intelligentsia Coffee that Legend wanted to try and re-caffeinated ourselves.
From there, we walked down to the Magnificent Mile, a long stretch of road filled with shopping. We checked out a few stores but didn’t buy anything. However – if you need clothes, you’ll find every shop you could dream of along this stretch. If you like to shop, be sure to plan to spend some time here. From there we just kept walking, checking out the city and buildings. We ended up walking along the river for a bit, which was very pretty.
We had dinner at a Thai place somewhere around where all the theaters are; I can’t find the place on Yelp so I think it might have closed. It wasn’t all that good so you’re not missing anything there! We finally called it a night and headed back to the hotel.
We both flew out in separate directions the next morning, and the next time I saw Legend was four months later when I arrived in Glasgow.
All in all, managing gluten free Chicago was pretty easy; as you’d expect, in a big city, people tended to be pretty knowledgeable about their ingredients. This trip wasn’t as planned and organized as I would have liked – usually I do lots of research and have a good idea of what to see and do, but this time, I’d done very little to prepare and we just kind of wandered. It was still fun, but I think we could have seen a lot more if we’d known what was around us.
Have you been to Chicago? Where is the best gluten free pizza you’ve ever eaten? Tell me in the comments!