Okay so last month I figured it was high time my family saw something besides our own backyard. Midwest road trip, right? Sounds simple. Spoiler: it wasn’t. Ended up wrestling with plans for weeks before we even packed a toothbrush. Wish I’d had these tips back then.
The Starting Point: Pure Overwhelm
Seriously, I opened my laptop, typed “best Midwest vacation spots”… and bam. Info overload. Lakes? Cities? Corn mazes? Everyone online just throws names at you. Needed a plan, a real one, not just pretty pictures.
Digging Deep: Figuring Out What We Actually Wanted
First thing I did was corner the wife and kids. “What do you losers actually want to do?” Sounds mean, but hey, gotta be honest. Turns out:
- The teenager basically demanded “not boring” and good phone pics.
- The little one just yelled “WATER PARK!” repeatedly.
- The wife gave me that look meaning “somewhere with actual beds, not a tent.”
- Me? I just wanted to drive without needing a second mortgage for gas.
Not exactly the Grand Tour dream, but honest. Midwest trip born.
My 8 Clumsy But Necessary Tips in Action
- Tip 1: Pick Your Actual Battles (Spots). Couldn’t do it all. Sorry, St. Louis Arch. We picked Chicago for hustle and Door County Wisconsin for chillin’, based purely on family screaming.
- Tip 2: Drive Times are Liars. Looked at the map, “Oh, just 5 hours!” Google forgot to mention road construction, pee breaks, and the sudden urge for cheese curds that adds two hours. Budgeted way more drive time. Still ran late.
- Tip 3: Book Sleep Before You Snore. Almost messed this up big time. Waited a week on a Chicago hotel… prices doubled. Panic-booked some place near the airport. Bit noisy, but saved cash. Lesson learned.
- Tip 4: Pack Like a Boy Scout, But Dumber. Seriously. Layers. Chicago winds are brutal one minute, sweaty the next. Packed hoodies and rain jackets and sunscreen. Still forgot my good hat.
- Tip 5: Eat Like a Local (Or At Least Not at Chain #42). Deep dish pizza? Yeah, obviously. But finding that tiny bakery in Wisconsin with mind-blowing cherry pie? Pure gold. Asked the grumpy guy at the gas station for recs. He was right.
- Tip 6: Chill the Heck Out & Just Wander. Had one perfect afternoon in Door County. No schedule. Just found a random beach, skipped rocks, watched the kids chase seagulls. Best moment, easy.
- Tip 7: Budget for “Oooh Shiny!” Syndrome. Look, that overpriced fudge shop? Resistance is futile. Budgeted extra cash for inevitable junk food/souvenir splurges. Kids got weird t-shirts. Everyone happy(ish).
- Tip 8: Apps Are Your Annoying Copilot. Used Google Maps offline like a paranoid weirdo. Also downloaded some random weather app that yelled at me about Wisconsin thunderstorms. Saved us from getting soaked once.
The Twist? It Went Wrong Anyway.
Yeah, following my own darn tips didn’t stop disaster. Hit crazy Chicago traffic. Like, “is this the apocalypse?” traffic. Missed our Navy Pier boat tour. Kids were mutinous. Ended up dragging everyone on an overpriced river cruise instead. They complained… until they saw the skyline. Total win, sort of. Point is, Midwest trips are messy by design. Embrace the chaos, pack snacks.
The Shocking Verdict
After all that planning, stressing, driving, spending… you know what? It was actually pretty great. Saw new places. Laughed a lot (mostly at each other). Ate too much cheese. Learned that Wisconsin mosquitoes are basically vampires. Would I do it again? Actually… yeah. Just maybe let the hotel room air out first next time.
