Day-by-day eating plans for Chicago. weekend classics, family routes, vegan plans, on-a-budget editions.
Day-by-day plans
Chicago coffee and bakery day ★ 4.5
Chicago built one of the deepest specialty coffee scenes in America, anchored by Intelligentsia, Dark Matter, Metric and Big Shoulders. The bakery culture runs alongside at Kasama, Defloured and Stan's Donuts. This single-day plan strings the canonical roasters and bakeries from morning to late espresso.
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Day 1: Day 1: morning bakery, lunch coffee, late espresso
- Morning
- Open at Kasama Bakery on Chicago Avenue from 07:00 for the Filipino-French morning bun and a flat white. Walk Ukrainian Village.
- Afternoon
- Lunch at Intelligentsia Monadnock for a single-origin filter and seasonal sandwich. Walk the Loop then on to Stan's Donuts.
- Evening
- Wind down at Dark Matter Coffee for a late espresso, then close at Sawada Coffee in the West Loop for the third roaster of the day.
Chicago weekend: the classics, done right ★ 4.5
A weekend built around Chicago's invented foods, the rooms that codified them, and one tasting menu to close.
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Day 1: Saturday: hot dog, Italian beef, deep-dish, cocktail
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Day 2: Sunday: brunch, market, tasting menu
Chicago family three days: friendly, fed, fun ★ 4.3
A three-day plan for a family with school-age kids: tactile food experiences, kid-friendly tables, plenty of cookies along the way.
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Day 1: Day 1: cinnamon rolls, river, hot dogs
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Day 2: Day 2: market, museum, taco lunch, pretzel dinner
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Day 3: Day 3: zoo, brunch, beach pizza
Chicago on a budget: under $40 a day ★ 4.3
A two-day plan to eat Chicago well for under $40 per person per day, leaning on taquerias, hot dog stands, Polish counters and Italian beef.
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Day 1: Day 1: beef, taco, tavern thin
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Day 2: Day 2: biryani, jibarito, popcorn, rib tips