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CaféWork-friendlyWifi
Sawada Coffee in Chicago is Hiroshi Sawada's West Loop cafe on Green Street, doored with Green Street Smoked Meats, home of the matcha-espresso-cocoa.
DrinkMilitary latte (matcha, espresso, cocoa)
TipThe window counter has the best light; the back of the room is louder than it looks because it shares with the BBQ kitchen.
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CaféWork-friendlyWifi
Intelligentsia in Chicago is the Monadnock Building flagship of the third-wave roaster (founded 1995 by Doug Zell) on Jackson Boulevard, with Black Cat.
DrinkBlack Cat espresso
TipOrder the Black Cat as a single-shot macchiato; it shows off the roast better than a long milk drink.
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CaféWork-friendlyWifi
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.
DrinkSingle-origin pour-over
TipAsk for the bar seat by the pour-over station; the baristas talk you through the cup as they brew it.
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CaféWork-friendlyWifi
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.
DrinkCortado
TipThe 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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CaféWork-friendlyWifi
Dark Matter in Chicago is the Ukrainian Village roaster cafe (the Mothership) on Chicago Avenue, a heavy roaster with Unicorn espresso and rotating gallery.
DrinkUnicorn espresso blend
TipThe cold brew on tap is the high point. Get one for the walk to the next stop on Chicago Avenue.
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CaféWork-friendlyWifi
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.
DrinkPop-culture latte art
TipCloses at 19:00 most nights. The back room is the working seat; the front is for picture-taking by the DeLorean.
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Café
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.
DrinkCoffee and the daily breakfast plate
TipCash only. The Obama-favorite tray is scrambled eggs, two sausages, hash browns and toast for under $7.
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Lou Mitchell's in Chicago is the West Loop diner on West Jackson since 1923, the historic Route 66 starting point breakfast, with Milk Duds passed out.
DrinkCoffee and Milk Duds at the door
TipOrder the Greek omelette and an orange-cup fresh juice. Saturday queue is 45 minutes; arrive at 07:30.
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CaféWork-friendlyWifi
La Colombe in Chicago is the West Loop branch on Randolph of the Philadelphia roaster, with the draft latte (nitrogen-infused) and a large airy front room.
DrinkDraft latte
TipDraft latte is the room's signature; buy the can to take home if you don't want to wait for the tap pour.
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CaféAvondaleWork-friendlyWifi
Milli by Metric is the 12,000-square-foot all-day Avondale cafe Metric Coffee opened in September 2025. Order the metric house espresso and seasonal filter.
DrinkMetric house espresso and seasonal filter