Let me set the scene: we’re navigating downtown Chicago traffic, cars are cutting us off from every direction, nobody’s using turn signals, and someone just ran a red light directly in front of us. This all happened in a five-minute stretch. Five minutes. And naturally, this was one of the rare times I was driving instead of Ethan, so maybe that explains why chaos always finds me behind the wheel. (Stuff always happens when I drive, which is probably why Ethan drives 99% of the time.)
Chicago drivers might be tied with Houston for the absolute worst we’ve encountered on the road. But you know what? Surviving that traffic was completely worth it, because we were in Chicago for one very specific reason: to see Wait Wait… Don’t Tell Me! recorded live.
Why Chicago? (Spoiler: NPR Made Us Do It)
We’ve been fans of WWDTM for years. When we found out they were recording an episode in Chicago at the end of July 2025, we knew we had to make it happen. This also lined up perfectly with our annual friend trip tradition. We try to do at least one big adventure with our Minnesota crew every year. Last year it was Chicago, and this year we’re hoping for San Diego or Hollywood (we’ll see!).
The plan was simple: meet up with Alex, Dan, Kev, and Leah in Chicago for a long weekend. We hadn’t seen them since Christmas 2024, so we were overdue for quality time. The timing was actually perfect too. We had tickets for the show on Thursday night, a full day Friday, a full day Saturday, and then we’d head out Sunday morning to pick up Rooster from his breeder in southern Indiana. (That 16-hour adventure back to Minnesota is a whole other blog post.)
The Urban Van Life Logistics Puzzle
Here’s the thing about visiting a major city in a van: there are no dispersed camping spots, no national forest pullouts, no quiet BLM land. Just urban parking lots and trying not to look too suspicious.
We stayed at a Home Depot in Evanston, which is in the northern part outside downtown. Overnight parking there was fine, and we felt safe the whole time. But during the day, we’d move the van to a nearby Walmart that had a bus station with access to the metro system. Most places only allow overnight parking and don’t want you staying long-term, so we got into a rhythm of moving during the day anyway.
Finding these spots took some research. We used crime maps and The Dyrt with reviews, but honestly, sometimes you just have to go off vibes and ask locals. We had a general idea of where it was safer to park overnight, and thankfully everything worked out. We used SpotAngels to find affordable parking that could actually fit our van. That app is a lifesaver in big cities.
The commute into downtown was about 45 minutes on the metro, but once we were in the city, we could walk almost everywhere or grab a quick Uber. Van life makes visiting cities way cheaper than you’d think. We’re basically just paying for gas and metro tickets, which are pretty affordable compared to hotel rates for a long weekend.
Was it complicated figuring out the metro system? Eh, medium complicated. We definitely got lost a few times and missed stops because we didn’t know exactly where to stand or which direction we needed. But with today’s technology, Reddit, and the apps we use, you get the hang of it pretty quickly. If we didn’t have any idea of the area beforehand, it probably would’ve been more challenging.
One thing that made us feel better about leaving the van during the day: we have security cameras we can check on our phones, plus a fan with temperature control and a separate temperature monitor. The cats (Mav and Goose at this point, no Rooster yet!) were perfectly fine with the setup, especially since the days were pretty cool.
Thursday: Deep Dish, Delayed Friends, and Dream Show
We arrived Thursday afternoon with one stop in mind before the show: Lou Malnati’s Pizzeria for Chicago deep dish. Get the butter crust, trust us. Also, get there with enough time to wait. We waited about an hour for a table, so just keep that in mind when you’re planning. The pizza was worth every minute of that wait though.
Plot twist: our friends were supposed to arrive Thursday afternoon too, but they got stuck in Minneapolis due to bad weather. Devastating for them, best day ever for us (sorry, friends).
The show was incredible. Peter Sagal and Bill Kurtis are exactly as you’d imagine them. Sharp, funny, completely in sync. The panelists that night were Joyelle Nicole Johnson, Adam Burke, and Peter Grosz, and they had Laufey as the guest. It was so cool seeing how they record everything, the behind-the-scenes banter between takes, the way they work the audience. If you’re a fan of the show, seeing it live is an absolute must. We were geeking out the entire time.
After the show, our friends had finally made it to Chicago, so we met them back at Lou Malnati’s so they could try the pizza too. We caught up, told them everything about the show they’d missed, and just enjoyed finally being together after months apart.
Friday: Tourist Mode Activated
Friday was full classic Chicago sightseeing. We hit the Bean (officially Cloud Gate, but come on, it’s the Bean), walked around downtown, and spent time at Navy Pier for lunch and more wandering. The weather was perfect for walking, which was good because we covered a lot of ground.
After all that walking, we headed back to our friends’ hotel to just hang out before the Cubs game that night. Sometimes the best part of trips with friends isn’t the activities. It’s just sitting around talking and laughing in a hotel room for a few hours.
The game that night was White Sox vs Cubs at Guaranteed Rate Field (the White Sox stadium), and let me tell you, the energy was incredible. We had no tie to either team, so we just got to enjoy the rivalry atmosphere without any stress. The Sox ended up winning, which made the crowd go absolutely wild. There’s something special about watching a game when you’re just there for the experience and the energy, not worried about who wins or loses.
We also tried Chicago hot dogs at the game, which is apparently a mandatory experience. Ethan loved it. I, however, was not a fan. Celery salt on a hot dog? Sorry Chicago, I’m not convinced. But hey, at least we can say we tried the real deal!
Saturday: The Bear, The Zoo, The Farewell Dinner
Saturday morning, Ethan and I snuck away from the group for a lunch that became my absolute favorite moment of the whole trip. We went to a place called The Beef for Italian beef sandwiches, and honestly, I could not have been more excited. The second we walked in, it felt exactly like the first episode of The Bear. This is the actual restaurant that inspired the show, and being there felt surreal. The energy, the setup, the whole vibe. I’m pretty sure I had the biggest smile on my face the entire time. We beat the lunch rush and got our sandwiches around 11am, which was perfect timing because by the time we left, the line was absolutely absurd.
If you’re a fan of The Bear, you have to go. The sandwiches are incredible, and the experience of being in that space where so much of the show’s authenticity comes from is worth the trip alone.
After lunch, we met back up with everyone and hit Millennium Park and Lincoln Park Zoo (which is free, by the way. One of the best free attractions in any major city). We spent the afternoon just enjoying the city before our final dinner together at Quartino that evening.
Quartino was the perfect send-off meal. Great food, great company, and that bittersweet feeling of knowing the weekend was ending. After dinner, we said our goodbyes and hit the road. We had about a four-hour drive south toward Indiana to get closer to Rooster’s breeder, and we wanted to get some miles behind us before calling it a night.
Would We Do It Again?
Absolutely. We loved WWDTM so much that we’d go back to Chicago just for another taping. Funny enough, we actually did end up back in Chicago about three weeks later in mid-August for a work meetup, so we got to experience the city twice that summer.
For other van lifers wondering if big cities are worth the logistical headache: yes, completely. Here’s what we learned:
Find overnight parking outside downtown. Evanston worked perfectly for us. Close enough to access the city, far enough to feel safe and have options.
Use the metro system. Driving downtown Chicago is for the bold and maybe the stupid (we totally did it, so maybe we’re both). The metro gets you everywhere you need to go.
Move your van during the day. Most places only allow overnight parking, so plan to relocate during the day anyway. We parked near metro access, which made getting into the city easy.
Use parking apps for downtown spots. SpotAngels was clutch for finding affordable parking that could fit our van when we needed to drive in.
Don’t stress about the cats. With fans, temperature monitoring, and security cameras, they were completely fine during our day adventures.
Plan one “just us” moment. That Italian beef lunch was my favorite part of the weekend. Sometimes you just need to sneak away for your own food adventure.
Van life works even in major cities. The logistics are a little trickier than pulling off into a national forest, but it’s absolutely doable and so worth it. Plus, there’s something satisfying about proving to yourself that you can make it work anywhere, even in downtown Chicago with the worst drivers we’ve ever encountered.
After that weekend, Ethan gladly took back his usual spot behind the wheel. Honestly, we were both relieved.
Wandering with Charlotte 
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