☕ Chicago Coffee Crawl: 6 Cozy Shops for the Perfect Fall Weekend

There’s something about crisp fall air, golden leaves, and the smell of espresso that just feels right. So this past weekend, I decided to do something I’ve been wanting to try for ages — a little solo (and very caffeinated) getaway to Chicago. No big agenda, just a long weekend of wandering, sipping, and soaking up the city in full autumn mode.

Here’s the plan I followed: one coffee shop in the morning, one in the afternoon, for two full days — and then one final double-header before heading home. It turned out to be the perfect rhythm — and now I’m sharing my top 6 coffee shop picks in case you want to recreate this little fall ritual yourself.

Day 1: Cozy Beginnings & Creative Sips

☀️ Morning Stop: Intelligentsia Coffee – Broadway

I kicked off the trip at Intelligentsia, a Chicago staple. Their Broadway location has the perfect neighborhood vibe — casual but elevated. I ordered a maple spice latte (because fall, obviously) and grabbed a seat by the window. It was the kind of slow, grounding start every weekend should have.

• My order: Maple spice latte + butter croissant

• Vibe: Calm, clean, early-morning energy

• 📍 3123 N Broadway St, Chicago, IL 60657

🍂 Afternoon Stop: Sawada Coffee – West Loop

Sawada is one of those spots that just feels cool without trying too hard. Industrial, moody lighting, and a matcha latte that completely lives up to the hype. I brought a notebook, stayed way too long, and left buzzing (in the best way).

• My order: Matcha cortado

• Vibe: Artsy, edgy, great people-watching

• 📍 112 N Green St, Chicago, IL 60607

Day 2: Bold Brews & Retro Vibes

☀️ Morning Stop: Dark Matter Coffee – Star Lounge

Day 2 started with a bang. Dark Matter doesn’t play around — their coffee is rich, flavorful, and just the right amount of weird (in a good way). The Star Lounge location is part coffee shop, part vintage living room. I could’ve stayed all day.

• My order: “Unicorn Blood” drip + almond milk

• Vibe: Loud, warm, unapologetically bold

• 📍 2521 W Chicago Ave, Chicago, IL 60622

🍂 Afternoon Stop: The Wormhole Coffee – Wicker Park

If you love a little nostalgia with your caffeine, The Wormhole is a dream. Think vintage movie posters, a DeLorean in the back, and some seriously good seasonal drinks. I sipped a caramel apple latte while flipping through a book I’d been saving. Perfectly cozy.

• My order: Caramel apple latte

• Vibe: Retro, playful, very “main character in a coffee shop” energy

• 📍 1462 N Milwaukee Ave, Chicago, IL 60622

Day 3: A Grand Finale

☀️ Morning Stop: Big Shoulders Coffee – River North

Before heading home, I made one final morning stop at Big Shoulders. Clean lines, great music, and a latte that hit just right. It felt like the grown-up version of all the cozy coffee shop moments I’d had that weekend.

• My order: Vanilla oat latte

• Vibe: Simple, polished, calm reset before re-entry

• 📍 858 N State St, Chicago, IL 60610

🍂 Afternoon Stop: Starbucks Reserve Roastery – Magnificent Mile

I wrapped up the trip with a little indulgence: the Starbucks Reserve Roastery. Yes, it’s corporate. Yes, it’s extra. But honestly? It’s worth it. Four floors of coffee experiences, a cocktail bar, pastries, experimental brews… it’s a coffee lover’s playground. I grabbed a seasonal espresso martini (because vacation), sat at the bar, and let the whole weekend settle in.

• My order: Espresso martini + roasted hazelnut affogato (check out our other classic fall rec's from Starbucks here)

• Vibe: Luxe, touristy (in a fun way), a true fall finale

• 📍 646 Michigan Ave, Chicago, IL 60611

The Takeaway

This little fall coffee crawl was exactly what I needed 🧡— slow mornings, sweet sips, and quiet pockets of joy in the middle of a buzzing city. If you’re planning a trip to Chicago this fall (or just want to romanticize your weekend), I highly recommend this kind of intentional, low-key itinerary.

It was also the perfect way to soak in seasonal inspiration — for drinkware, table styling, and even content planning. I found myself dreaming up new color palettes and product names in every cozy corner.

So pack a bag, grab your favorite tumbler, and plan your own version of this pour-over weekend. You deserve it.