Chicago river & skyline
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🎊
The mission, should you choose to accept it: get Nate properly, thoroughly, deep-dish-fully celebrated in Chicago.
📍 Chicago, IL · September 25, 2026 → September 28, 2026
🏠 Home base: 2154 W Ohio St, 1E · Airbnb listing
✨ Gayle's hotel: The Pendry — 230 N Michigan Ave
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⚡ Locked In Items
The four things to build your weekend around — everything else is optional fun:
- 🎂 Friday 8:00pm — Birthday dinner at Ada Street (booked — just show up hungry)
- 🚤 Saturday 4:30pm — Sunset River Architecture Tour — whole group, no exceptions
- 🏅 Sunday early AM — Chicago Half Marathon (racers run, everyone else cheers and eats junk food)
- 🍕 Sunday 6:00pm — Pequod's deep dish, then 🎵 Kingston Mines blues at 8:00pm
🥯 Friday, Sept 25 — Arrival & the Birthday Dinner
Chicago at night
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🧳
Check-in isn't until 4:00pm — we're working on an early luggage drop at the Airbnb garage. If that falls through: bags go to friends nearby and we bike the west side instead.
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- Midday — Land, drop bags, exhale
- Afternoon (optional) — Lunch at Small Cheval 📍 Map or a Divvy ride on the 606 trail 📍 Map
- Evening — Pre-dinner drinks (spot TBD — watch the group chat)
- 8:00pm — 🎂 Nate's Birthday Dinner at Ada Street 📍 Map — booked, nothing to do but show up
- Late — Nightcap at Third Rail 📍 Map or Damen Tavern 📍 Map
🏛️ Saturday, Sept 26 — The Bean, the Art & the River
Cloud Gate, Millennium Park