A city with a landmark called “The Bean” feels like a quiet promise that coffee matters here — and Chicago absolutely delivers.

Morning + Afternoon Stops to Explore

Stop 1: Intelligentsia Coffee – Broadway (Lakeview)

One of Chicago’s most beloved coffee institutions, Intelligentsia’s Broadway location is a perfect first stop. The vibe is welcoming yet refined — great for easing into the day.

Why go: Classic espresso drinks, consistent quality, neighborhood atmosphere
Try: A latte or your favorite espresso drink with a pastry
📍 3123 N Broadway, Chicago, IL

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Stop 2: Sawada Coffee – West Loop

A beloved local spot with a distinct energy and plenty of personality. Sawada’s matcha and espresso drinks have a loyal following and make for a refreshing midday pick-me-up.

Why go: Unique drinks, creative presentation, relaxed vibe
Try: Matcha cortado or signature espresso drink
📍 112 N Green St., Chicago, IL

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Stop 3: Dark Matter Coffee – Star Lounge (West Town)

Dark Matter is known for rich, bold coffee and an atmosphere that feels like a cozy neighborhood hangout. Each location has its own character, and the Star Lounge blends richly roasted brews with inviting communal space.

Why go: Bold flavors, playful aesthetic, perfect for lingering
Try: Any dark roast coffee or seasonal pour-over
📍 2521 W Chicago Ave., Chicago, IL

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Stop 4: The Wormhole Coffee – Wicker Park

For a dose of nostalgia alongside your caffeine, The Wormhole delivers. With its retro décor (including a DeLorean in the corner) and friendly service, it’s a destination for both coffee and ambiance.

Why go: Retro surroundings, comfortable seating, fun vibe
Try: Caramel latte or your favorite seasonal flavor
📍 1462 N Milwaukee Ave., Chicago, IL

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Stop 5: Big Shoulders Coffee – River North

Big Shoulders strikes the balance between cozy and polished — ideal for reflecting on your crawl so far or squeezing in one last cup before the day transitions. Great music and a simple, satisfying menu.

Why go: Calm reset, quality coffee, good atmosphere
Try: Vanilla oat latte or classic drip
📍 858 N State St., Chicago, IL

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Stop 6: Starbucks Reserve Roastery – Magnificent Mile

For a different kind of coffee experience, the Starbucks Reserve Roastery is worth a stop. While it’s a larger, more corporate setting than the others on this list, the multi-floor space offers innovative brews, unique pours, and even crafted coffee cocktails — a fun way to end your crawl.

Why go: Unique coffee experiences, specialty drinks, memorable atmosphere
Try: Specialty espresso flight or Reserve pour-over
📍 646 Michigan Ave., Chicago, IL

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How to Make This Your Own

A coffee crawl doesn’t need to be rigid — swap in neighborhood favorites, take breaks for snacks or people-watching, and give yourself permission to meander between stops. Chicago’s coffee scene thrives on variety, community, and creativity. Let your day unfold in a way that feels joyful and unhurried — just like your pour. ☕

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Tips for Coffee Day Adventures

• Plan your route ahead of time: Chicago is big, and many coffee neighborhoods are walkable if you group stops by area.
• Try something new: Ask baristas for their favorite drink if you’re unsure what to order.
• Take breaks: Coffee crawls are about the experience — not just the caffeine. Enjoy pauses, people-watch, and the vibe of each place.
• Bring a reusable tumbler: Sustainable and perfect for extending sipping moments throughout the day.

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Found A Favorite? Recreate it!

Found a latte that you can’t shake? When we got home we had post coffee crawl blues too, it’s hard to shake when you’ve had a perfect cup! Part of the follow up fun can be a quest to try and recreate the magic back at home. See our favorite coffee makers and resources to try and recreate your favorite drink from the crawl!

Please leave us a comment on your favorite Chicago coffee stops and which drinks are your favorite!