THEMOVE

Chicago /

North Side

The Wells Street Classic

first-date~$180–280 for twoNorth Side

  1. 6:00 PM Dinner at Kayao, 1252 N Wells — Peruvian-Nikkei — reserve
  2. 7:30 PM Two blocks up to Jeni's for a scoop
  3. 7:50 PM Doors at The Second City, 1616 N Wells — 8 PM Mainstage revue, Tue–Sun
  4. 10:00 PM Post-show drink back on Wells if the night's going well

Why it lands: Dinner, ice cream stroll, and the sketch stage that launched half of SNL — all on the same three blocks, zero logistics.

Weather backup: Everything's indoors and the walks are under five minutes. This one doesn't check the forecast.

On the radar in North Side

Proven spots in North Side

Kayao

Peruvian-Nikkei dinner · Old Town · $$$

Peruvian × Japanese mashup on Wells — adventurous without being intimidating.

The Second City Mainstage

Comedy institution · Old Town · $$$

The SNL pipeline, live. Guaranteed laughs and built-in conversation after.

Jeni's Splendid Ice Creams

Dessert & stroll · Old Town · $

Half a block from Second City — the obvious pre-show scoop.

One email. Friday plans, done.

Every Thursday morning: this week's best dates in your city, fully planned — book one thing, look like you did the research. Free.

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