Cheap flights from San Francisco to Chicago

One-way fares from $108 · SFO → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → San Francisco
Cheapest fare
$108

Alaska Airlines · Mon, Nov 23

Cheapest month
November

from $108

Direct flights
Not recently

Usually 1+ stop

Quickest trip
5h 02m

2,990 km

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Cheapest month to fly from San Francisco to Chicago

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $108
  2. March 2027 $203

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

Alaska Airlines
Depart08:25 Mon, Nov 23SFO → ORD 5h 57m · 1 stop
$108one way, per person
View deal
Frontier Airlines
Depart15:41 Thu, Nov 26SFO → ORD 5h 06m · 1 stop
$122one way, per person
View deal
Frontier Airlines
Depart21:23 Wed, Nov 25SFO → ORD 5h 02m · 1 stop
$128one way, per person
View deal
Frontier Airlines
Depart18:04 Thu, Nov 12SFO → ORD 6h 19m · 2 stops
$167one way, per person
View deal
Frontier Airlines
Depart22:20 Thu, Nov 5SFO → ORD 6h 57m · 1 stop
$192one way, per person
View deal
See every date in November 2026 →

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Where to stay, what to do and getting around, from our travel partners.

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Getting around

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About flights from San Francisco to Chicago

San Francisco (SFO) and Chicago (CHI) are about 2,990 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 5h 02m. Over the next few months, one-way fares start from $108, 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 San Francisco to Chicago?

The cheapest one-way fare we've seen recently is $108 with Alaska Airlines, departing Monday, November 23, 2026. Over the coming months, the lowest fare in each month ranges from $108 to $203.

What is the cheapest month to fly from San Francisco to Chicago?

November 2026 currently has the lowest fares, from $108 one way.

Are there direct flights from San Francisco to Chicago?

We haven't seen direct fares recently, so most journeys include at least one stop.

How long is the flight from San Francisco to Chicago?

The quickest journey we've seen takes about 5h 02m. San Francisco and Chicago are around 2,990 km apart.

Which airlines fly from San Francisco to Chicago?

Recent fares on this route were with Alaska Airlines and Frontier Airlines.

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