Friday
- 8:00 PM
Girl & The Goat
Modern American · $$$ · West LoopKick the night off — Stephanie Izard's wood-fired plates, share everything.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in West Loop — short walk from your other stops
- ·A shoulder-season favorite
- 2:00 AM
Au Cheval
Diner / Burgers · $$ · West LoopLate-night fix — Two-hour wait for the country's most-talked-about cheeseburger.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in West Loop — short walk from your other stops
- ·A shoulder-season favorite
Saturday
- 12:00 PM
Pequod's Pizza
Deep-dish · $$ · Lincoln ParkRecovery brunch — Caramelized cheese crust — the locals' deep-dish pick.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in Lincoln Park — short walk from your other stops
- ·A shoulder-season favorite
- 3:00 PMMillennium ParkOutdoors · Loop
Anish Kapoor's Bean (Cloud Gate), free concerts at Pritzker Pavilion.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in Loop — short walk from your other stops
- ·A shoulder-season favorite
- 8:30 PM
Lou Mitchell's
Diner · $ · West LoopRoute 66 diner since 1923 — fluffy omelets and free Milk Duds.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in West Loop — short walk from your other stops
- ·A shoulder-season favorite
- 12:30 AM
Bar-hop the district
Pick the busiest nightlife strip and crawl three rooms — sports bar warm-up, cocktail lounge, then dance floor.
Sunday
- 1:00 PM
Alinea
Modernist tasting · $$$$ · Lincoln ParkSlow brunch — Grant Achatz's three-star theater on a plate.
Why this pick- ·Built for a real boys' night — high energy, late hours
- ·Keeps you in Lincoln Park — short walk from your other stops
- ·A shoulder-season favorite
Want a different vibe?
Try one of the other ready-made Chicago plans.