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.
Tip: Order the Black Cat as a single-shot macchiato; it shows off the roast better than a long milk drink.
Address: 53 W Jackson Blvd, Chicago, IL 60604
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.
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.
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.
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.
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 at the door.
Signature drink: Coffee and Milk Duds at the door
Tip: Order the Greek omelette and an orange-cup fresh juice. Saturday queue is 45 minutes; arrive at 07:30.
