Chicago skyline with Willis Tower and Lake Michigan
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The Quick Business Trip

Chicago, IL

Sales VP, 47, needs to be in Chicago for a client dinner. Budget: Company policy allows up to $800 for domestic flights. Here's how we turned their vision into a booked trip.

3 minutes
Time to book
Tomorrow
Planning window
$347 outbound
Final price
12-15 minutes
Time saved

The Brief

"ORD tomorrow, any afternoon flight, economy is fine, aisle. Back Thursday red-eye."

Their requirements:

  • American AAdvantage member
  • Seat preference: Aisle
  • TSA PreCheck number on file
  • Work email for receipts

Our Process

What we ruled out:

  • × United 892 — $312, but wouldn't earn AA miles

What we considered:

  • AA 1245 — 2:15pm, aisle 14C, $347
  • AA 1892 — 4:30pm, aisle 12D, $289

The Booking

American Airlines 1245, Seat 14C + Thursday red-eye return

  • Why it won: Met timing requirements, earns miles, aisle seat
  • Price: $347 outbound
  • Extras added: AAdvantage miles earned automatically, receipt sent to work email

The Outcome

DIY Research Estimate

12-15 minutes

With Otherwhere

3 minutes


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