MySitti
Your AI travel companion

Chicago, Illinois is 16 days away ✦

I'm watching your trip around the clock — flights, weather, events, and everything you still need to do. Here's where things stand today.

16
days to go
4
nights
5
days planned
3
events saved
78°F
avg. forecast
Reminders — the road to takeoff
THIS WEEK
Book your hotel
The Langham river-view rooms for your dates historically sell out ~2 weeks ahead. You're inside the smart-booking window now.
THIS WEEK
Lock in flights
Fares to ORD for late August are in the normal range. Best window: Friday morning out, Tuesday evening back.
AUG 14
Buy remaining event tickets
Salt Shed (Billy Currington & Kip Moore) is an outdoor show — these move fast in good-weather forecasts.
AUG 19
Packing day
I'll send your packing list for the trip — matched to the forecast for your dates.
AUG 20
Check in for your flight
I'll remind you the minute check-in opens, with your terminal and CTA Blue Line directions ready.
Day 1 briefing — preview

Every morning of your trip, I'll drop a briefing like this before you're out of bed.

Friday, Aug 21 — Arrival day

Landing early afternoon — the Blue Line beats a rideshare to downtown at that hour (45 min, $5). Drop bags in Lincoln Park, then golden hour on the Riverwalk around 6:40 PM. Your deep-dish table at Gino's Eastis best booked for 7:30 — they don't take same-day walk-ins lightly on Fridays. Tonight's alternative if energy is high: blues at Kingston Mines runs till late.

Ask Sitti anything, anytime

“Is the Salt Shed show rain-or-shine? What should we do if it rains Sunday? Where's the best skyline photo at night?” — I know your itinerary, your dates, and your city. Ask away.

Budget tracker

Planned vs. your $2,400 comfort budget.

Hotel · 4 nights$880 – 1,050
Flights · 2 travelers$340 – 520
Food & drinks~$430
Activities & tours~$260
Total planned$2,090 – 2,440
Estimates — live prices always on the booking platforms.
Forecast watch
Fri Aug 2179° · sunny
Sat Aug 2281° · sunny
Sun Aug 2377° · pm clouds
Mon Aug 2474° · showers?
Tue Aug 2576° · sunny
Monday looks damp — good thing that's museum day. I'll re-check daily and re-plan if needed.
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