What is the cheapest month to fly from Chicago to Southend?

Based on current 6-month forward fare data, October 2026 is the cheapest month to fly from Chicago (ORD) to Southend (SEN), with fares starting from $378.

What is the lowest current fare from ORD to SEN?

The lowest currently-listed fare from Chicago (ORD) to Southend (SEN) is $378 on 2026-10-07.

Is there a direct flight from Chicago to Southend?

There is currently no non-stop service from ORD to SEN. Most travellers connect through a hub airport. See our route page for current stopover options.

Cheap flights from Chicago to Southend

Cheapest current fares: $378 in October 2026 on connecting flights.

Last updated August 8, 2026 · By Flightmaps Editorial

Cheapest month-by-month fares

Lowest available fare per calendar month from Chicago (ORD) to Southend (SEN). Refreshed daily.

Chicago (ORD) → Southend (SEN)

October 2026 $378
August 2026 $435
December 2026 $502

Frequently asked questions

What is the cheapest month to fly from Chicago to Southend?

Based on current 6-month forward fare data, October 2026 is the cheapest month to fly from Chicago (ORD) to Southend (SEN), with fares starting from $378.
What is the lowest current fare from ORD to SEN?

The lowest currently-listed fare from Chicago (ORD) to Southend (SEN) is $378 on 2026-10-07.
Is there a direct flight from Chicago to Southend?

There is currently no non-stop service from ORD to SEN. 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.