Cheap flights from San Francisco to Chicago from $143 SFO → MDW, ORD, RFD

Found recently, and the cheapest we hold

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $116 to $301.

At $333, the cheapest return found recently is above that range.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other 6-night return fares leaving within 3 days of 25 Dec to compare.

Every date we hold

120 fares on 6 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $217.

Found recently, and the cheapest we hold

It is also the cheapest one-way we hold, of any age.

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $85 to $203.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

No. We hold one-way fares on 1 other departure date within 3 days of 25 Dec, and it is not cheaper.

Every date we hold

5 fares on 5 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $143.

Return

Fares 30 to 59 days before departure were typically 40% lower than 0 to 6 days before departure.

From the cheapest return each day between 24 Sept and 11 Nov (49 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

One-way

Fares 60 to 89 days before departure were typically 30% lower than 30 to 59 days before departure.

From the cheapest one-way each day between 24 Sept and 11 Nov (49 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

How much is a return flight from San Francisco to Chicago?

The cheapest return found recently is $333 with Frontier Airlines, 25 Dec to 31 Dec, found yesterday. The cheapest return we hold, of any age, is $217 with Frontier Airlines, 7 Dec to 10 Dec, found 7 days ago. The cheapest return fare on each of 6 departure dates is usually $334 to $373.

How much is a one-way flight from San Francisco to Chicago?

The cheapest one-way found recently is $143 with Frontier Airlines, 25 Dec, found yesterday. The cheapest one-way fare on each of 5 departure dates is usually $177 to $193.

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

December 2026 is the cheapest month for a return, from $217, 7 Dec to 10 Dec, found 7 days ago. It is the cheapest month for a one-way too, from $143, 25 Dec, found yesterday.

How far ahead should I book a flight from San Francisco to Chicago?

In 49 days of prices between 24 Sept and 11 Nov, return fares 30 to 59 days before departure were typically 40% lower than 0 to 6 days before departure. One-way fares 60 to 89 days before departure were typically 30% lower than 30 to 59 days before departure.

Is there a direct flight from San Francisco to Chicago?

Yes, the cheapest nonstop return found recently is $379 with American Airlines, 30 Dec to 3 Jan 2027, found 3 days ago.

How long is the flight from San Francisco to Chicago?

The cheapest one-way found recently, with Frontier Airlines on 25 Dec, takes 6 h 33 min with 1 stop.

Which airlines have the cheapest flights from San Francisco to Chicago?

Between 7 Dec and 1 Jul 2027, Frontier Airlines has the cheapest return on 4 of the 6 departure dates we hold, and Alaska Airlines on 2. Between 24 Dec and 19 Apr 2027, Alaska Airlines has the cheapest one-way on 3 of the 5 departure dates we hold, and Frontier Airlines on 2.