Cheap flights from Southend to Chicago
Cheapest current fares: $473 in October 2026 on connecting flights.
Cheapest month-by-month fares
Lowest available fare per calendar month from Southend (SEN) to Chicago (ORD). Refreshed daily.
Southend (SEN) → Chicago (ORD)
- October 2026 $473
- September 2026 $506
- August 2026 $678
Frequently asked questions
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What is the cheapest month to fly from Southend to Chicago?
Based on current 6-month forward fare data, October 2026 is the cheapest month to fly from Southend (SEN) to Chicago (ORD), with fares starting from $473.
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What is the lowest current fare from SEN to ORD?
The lowest currently-listed fare from Southend (SEN) to Chicago (ORD) is $473 on 2026-10-12.
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Is there a direct flight from Southend to Chicago?
There is currently no non-stop service from SEN to ORD. Most travellers connect through a hub airport. See our route page for current stopover options.
Related guides for this route
Sibling pages — full route detail, airport overviews, visa context, per-airline routes.