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Intelligentsia in Chicago is the Monadnock Building flagship of the third-wave roaster (founded 1995 by Doug Zell) on Jackson Boulevard, with Black Cat espresso.
Signature drink: Black Cat espresso
Tip: Order the Black Cat as a single-shot macchiato; it shows off the roast better than a long milk drink.
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Metric Coffee in Chicago is Xavier Alexander and Darko Arandjelovic's West Town roaster-cafe on Fulton, in a former blacksmith shop, with single-origin pour-overs.
Signature drink: Single-origin pour-over
Tip: Ask for the bar seat by the pour-over station; the baristas talk you through the cup as they brew it.
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Big Shoulders Coffee in Chicago is the Noble Square cafe on Chicago Avenue with a strong cortado and a small back room of communal-table seating for the laptop hour.
Signature drink: Cortado
Tip: The breakfast bagels from Beard Papa next door work well at this counter; carry one in and pair it with a cortado.
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Dark Matter in Chicago is the Ukrainian Village roaster cafe (the Mothership) on Chicago Avenue, a heavy roaster with Unicorn espresso and rotating gallery walls.
Signature drink: Unicorn espresso blend
Tip: The cold brew on tap is the high point. Get one for the walk to the next stop on Chicago Avenue.
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The Wormhole in Chicago is the Wicker Park cafe on Milwaukee Avenue with a DeLorean in the shop, pop-culture latte art and a comfortable back-room study scene.
Signature drink: Pop-culture latte art
Tip: Closes at 19:00 most nights. The back room is the working seat; the front is for picture-taking by the DeLorean.
Valois Cafeteria in Chicago is the Hyde Park cafeteria on 53rd Street since 1921, an Obama-era regular, with the See Your Food sign and a steam-table breakfast.
Signature drink: Coffee and the daily breakfast plate
Tip: Cash only. The Obama-favorite tray is scrambled eggs, two sausages, hash browns and toast for under $7.