🏡🌮 Chicago Day 3 Itinerary — Oak Park, Pilsen & Chinatown!
For Day 3, venture beyond downtown Chicago and spend the day exploring three completely different neighborhoods and areas: Oak Park, Pilsen, and Chinatown! 🏡🎨🏮
This itinerary is perfect if you love architecture, local food, art, neighborhood exploring, and discovering parts of Chicago with completely different personalities. Plus, you can do the entire day using public transit! 🚇
🥐 Take the Green Line to Oak Park & start at Broken Tart
Start your morning by hopping on the CTA Green Line and heading west to Oak Park.
First stop: Broken Tart, an absolutely adorable neighborhood bakery and café. Everything we tried was incredible, but I especially recommend the biscuits, banana bread, or cookies. Honestly, you really can’t go wrong here! 🍪🍌
It’s the perfect cozy start before a morning of architecture and exploring.
🏡 Tour the Frank Lloyd Wright Home & Studio
After breakfast, walk over to the Frank Lloyd Wright Home and Studio for a guided tour!
Even if you’re not an architecture expert, this is such an interesting experience. You’ll learn about Frank Lloyd Wright’s life and career while actually walking through the home and studio where he lived, experimented with design, and developed some of the ideas that would define his work.
There are so many beautiful architectural details to notice throughout the house, so take your time looking around! ✨
🎁 And definitely stop in the gift shop afterward. There were tons of beautiful and surprisingly well-priced gifts and souvenirs.
🏘️ Take an architecture walk through Oak Park
Before leaving, spend a little time walking around the surrounding neighborhood. Oak Park has an incredible concentration of homes designed or remodeled by Frank Lloyd Wright, so the architecture tour doesn’t have to end when you leave his studio!
Just remember that these are real homes where people actually live, so admire and photograph them respectfully. 📸
🌮 Next stop: Pilsen!
For the second part of the day, make your way to Pilsen, one of Chicago’s most vibrant Mexican-American neighborhoods.
Come hungry because your first stop should be Carniceria Maribel for some incredibly delicious and authentic Mexican food. 🇲🇽 This food stop is in the back of a bodega, so don’t be afraid or back out when you walk in and don’t see it. Just keep walking to the back and soon you’ll be greeted with an amazing smell!
🌮 GET THE TACOS. They’re packed with flavor and absolutely worth the trip!
🎨 Visit the National Museum of Mexican Art
After lunch, head over to the National Museum of Mexican Art, one of my biggest recommendations in Pilsen.
Best of all: admission is FREE! 🙌
The museum showcases an incredible collection of artwork by Mexican artists and art exploring Mexican identity, history, culture, and experiences in both Mexico and the United States. It’s a wonderful cultural stop and easily worth fitting into your Chicago itinerary.
🖼️ Explore Pilsen’s murals & street art
Don’t immediately leave after the museum! Part of the fun of visiting Pilsen is simply walking around and seeing the neighborhood itself.
Keep an eye out for the colorful murals and street art covering buildings, walls, and viaducts throughout the area. 🎨📸 There are beautiful works everywhere, so give yourself some time to wander!
🏮 Finish the day in Chicago’s Chinatown
For the final part of the day, head to Chinatown!
🚇 CTA tip: If you’re taking the Red Line south, check whether there’s a baseball game happening that day. The trains can get VERY crowded with fans heading toward the stadium!
🥢 Put your name down at Chubby Skewers FIRST
If you’re planning to eat at Chubby Skewers, make this your first stop when you arrive in Chinatown.
There WILL probably be a wait. We waited around 1 hour and 45 minutes for our table! 😳
But don’t let that scare you away. Put your name down immediately and use the wait as your built-in Chinatown exploration time.
And yes — I thought it was worth the wait! 🍢 The ingredients were great quality, there’s a huge variety to choose from, and the different spice mixes and seasonings were SO flavorful.
🛍️ Explore Chinatown while you wait
Now you have the perfect excuse to wander!
Explore the plazas, side streets, shops, bakeries, restaurants, and drink spots throughout Chinatown. Some fun places to check out include The Midi, Ichiban Candy & Snacks, and Joy Yee. 🧋🍬
📸 Don’t forget to look UP!
Head to the second level of Chinatown Square for some fantastic photo opportunities.
The elevated walkways give you great perspectives looking down into the alleys and plaza, and you can also get some really cool urban shots incorporating the Chicago skyline, CTA station, and elevated train tracks. 🚇🏙️
Chinatown is especially fun to photograph as the sun starts going down and everything begins lighting up!
🍢 Finally, dinner at Chubby Skewers!
Once your table is ready, head back for dinner and start ordering!
One of the best things about this restaurant is the variety, so it’s a great opportunity to order lots of different skewers for the table and try a little bit of everything. The seasoning makes it especially memorable. 🌶️🥢
🍵 End with dessert at Matcha En
You can’t end the night without dessert!
Head to Matcha En for a selection of delicious matcha drinks and Japanese-inspired sweets. 🍵💚
If you can’t decide what to order, go for the taiyaki! 🐟 It’s the perfect sweet ending after a long day of exploring.
✨ DAY 3 COMPLETE! ✨
This was one of my favorite ways to experience how diverse Chicago and the surrounding area can be. In a single day, you can go from the quiet, architecture-filled streets of Oak Park 🏡 to the colorful murals and Mexican-American culture of Pilsen 🎨🇲🇽 and finally the food, shops, lights, and energy of Chinatown 🏮🥢.
🚇 Tip: This itinerary covers a LOT of ground, so use the CTA whenever possible and wear comfortable shoes. Each area is also worth slowing down for — the best parts aren’t necessarily individual attractions, but all the little things you’ll discover while walking between them.
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