American AirlinesDepart15:16
Sat, Nov 14SWO → ORD
4h 06m · 1 stop
$269one way, per person
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- Cheapest fare
- $269
- Cheapest month
- November
- Direct flights
- Not recently
- Quickest trip
- 4h 06m
American Airlines · Sat, Nov 14
from $269
Usually 1+ stop
1,030 km
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Cheapest month to fly from Stillwater to Chicago
Lowest one-way fare per person in each month. Choose a month to see every date.
Cheapest dates in November 2026
The lowest fares we've seen for each day, cheapest first.
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About flights from Stillwater to Chicago
Stillwater (SWO) and Chicago (CHI) are about 1,030 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 4h 06m. Over the next few months, one-way fares start from $269, and November 2026 is currently the cheapest month to fly.
These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.
Frequently asked questions
How much is a flight from Stillwater to Chicago?
The cheapest one-way fare we've seen recently is $269 with American Airlines, departing Saturday, November 14, 2026.
What is the cheapest month to fly from Stillwater to Chicago?
November 2026 currently has the lowest fares, from $269 one way.
Are there direct flights from Stillwater to Chicago?
We haven't seen direct fares recently, so most journeys include at least one stop.
How long is the flight from Stillwater to Chicago?
The quickest journey we've seen takes about 4h 06m. Stillwater and Chicago are around 1,030 km apart.
Which airlines fly from Stillwater to Chicago?
Recent fares on this route were with American Airlines.
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