🦖🍜 Chicago Day 2 Itinerary — Hidden Gems, Amazing Food & Weird Chicago
Ready to explore beyond the usual Chicago tourist spots? 👀 Day 2 is all about dinosaurs, Pokémon, incredible neighborhood food, quirky shops, horror, taxidermy, local bakeries, and some genuine hidden gems. This is a GREAT itinerary if you want to see a completely different side of Chicago! 🏙️
🍵 Start with matcha at Foxtrot Market
Start the morning in River North with a matcha from Foxtrot Market before hopping on the CTA and heading south toward Museum Campus.
🦖 Spend the morning at the Field Museum
Give yourself PLENTY of time for the Field Museum because this place is absolutely massive. You could easily spend hours wandering through its exhibits.
Some highlights include Ancient Americas, The Changing Face of Science, Regenstein Halls of the Pacific, Abbott Hall of Conservation: Restoring Earth, Native Truths: Our Voices, Our Stories, and the incredible Griffin Halls of Evolving Planet, where you’ll find Chicago icon SUE the T. rex! 🦖
And, of course… Pokémon. ⚡️
The Pokémon Fossil Museum is a must for Pokémon fans. It uses Pokémon alongside real-world fossils to teach you about paleontology, fossilization, and excavation. Seeing Pokémon fossils compared with actual prehistoric specimens is such a fun concept!
🎟️ Important: You’ll need a separate timed ticket, so BOOK IN ADVANCE! Even with limited admission, the exhibit space itself is fairly small and can get crowded — especially with lots of excited kids — but it’s absolutely worth checking out.
🍌 Take the CTA to Ukrainian Village for a jibarito
Now for one of my favorite food discoveries of the trip: Smash Jibarito!
A jibarito replaces the bread of a traditional sandwich with crispy fried plantains, and the result is delicious. 🤤 The jibarito here was one of the best and most interesting takes on a “burger” I’ve ever had.
If you want to try something you probably aren’t eating every day back home, PUT THIS ON YOUR LIST.
💩 Make a pilgrimage to the St Fountain
Yes. The St Fountain. 😂
This is absolutely a “we’re nearby, so why not?” attraction, but that’s exactly what makes it fun. Stop by, take your obligatory photo, send it to your friends with zero context, and continue on your way.
🥐 Try Kasama… if you planned ahead!
The acclaimed Filipino bakery and restaurant Kasama is right around the corner. If this is high on your list, plan ahead! We arrived to find a line stretching down the street and unfortunately had to skip it. 😭
🥧 Get a local slice at Hoosier Mama Pie Company
Time for first dessert! Hoosier Mama Pie Company has tons of delicious and often seasonal flavors. It feels like the kind of neighborhood bakery you hope to stumble across while traveling, so grab a slice and see what’s available that day. 🥧
🚇 Find the perfect souvenir at Transit Tees
Public transit nerds, this one is for you. 🚇 Transit Tees has tons of Chicago-inspired designs and CTA-themed merch that make for MUCH more interesting keepsakes than another generic Chicago magnet.
🥐 Make another bakery stop at Mindy’s
Still capable of eating? Excellent.
Stop at Mindy’s Bakery for another sweet treat. 🍪 If you happen to visit toward the end of the day, check out the remaining pastry selection — we found pastries discounted 50% before closing, which made this stop even sweeter.
🔪 Enter horror heaven at The Brewed
Horror fans NEED to check out The Brewed. ☕️🩸 This horror-themed café is packed with creepy decor and themed drinks, making it one of the coolest coffee shops we found in Chicago.
💿 Browse Bric-a-Brac Records
Conveniently, Bric-a-Brac Records is right next door! Flip through their huge selection of old and new records and enjoy all the wonderfully weird stuff packed into the shop.
🦋 Discover one of Chicago’s coolest hidden gems: The Insect Asylum
DO. NOT. SKIP. THIS. PLACE.
The Insect Asylum is a taxidermy museum filled with fascinating specimens, insects, bones, oddities, and even LIVE animals. 🦎🕷️🐢
We saw a tortoise, birds, iguanas, tarantulas, and tons of incredible taxidermy. Tickets were $25 when we visited, and somehow we had the entire museum to ourselves for about an hour!
It was peaceful, fascinating, a little bizarre, and the perfect escape from the Chicago summer heat. Easily one of the biggest hidden gems of the trip. 💯
🍜 Dinner at Akahoshi Ramen
After all that exploring, head to Akahoshi Ramen for dinner.
My order: Aburasoba + Extra Shio Koji Chicken Breast.
The noodles were insanely flavorful and the chicken was SO good. This was easily one of my favorite meals of the day and a fantastic way to end an afternoon of exploring the neighborhoods.
🍦 Dessert at Pretty Cool Ice Cream
Except we’re obviously not actually done eating.
Right across the street is Pretty Cool Ice Cream, an adorable shop specializing in creative ice cream bars! I got the Caramel Horchata Crunch and it was to die for. 🍦
🎬 BONUS: End the night with a 4DX movie
Still have energy? Head to Regal City North and see something in 4DX! 🎥💨💦
If you’ve never experienced one, 4DX turns the movie into basically a theme park ride with moving seats and physical effects synchronized with what’s happening on screen. It’s a chaotic and extremely fun way to end the night.
✨ DAY 2 COMPLETE! ✨
This day takes you away from some of the biggest downtown attractions and into a completely different Chicago — incredible neighborhood restaurants, independent businesses, weird roadside-style attractions, horror, museums, and some of the best food of the trip.
🚇 Tip: The CTA makes this itinerary very doable without a car, but you’ll be moving through several different neighborhoods, so give yourself plenty of time and don’t feel like you need to hit every single stop.
And COME HUNGRY. Seriously. 😂
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