Cheap flights from Chicago to San Francisco from $187 MDW, ORD, RFD → SFO

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 $214 to $354.

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

Could nearby dates be cheaper?

We hold no other 8-night return fares leaving within 3 days of 5 Jan 2027 to compare.

Every date we hold

227 fares on 10 departure dates

Which month looks cheapest?

December 2026 is the cheapest month — from $214.

Found recently, and the cheapest we hold

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $57 to $182.

At $187, the cheapest one-way 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 one-way fares leaving within 3 days of 10 May 2027 to compare.

Every date we hold

9 fares on 4 departure dates

Which month looks cheapest?

February 2027 is the cheapest month — from $140.

Return

Fares 30 to 59 days before departure were typically 30% 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

The cheapest fares were 14 to 29 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 Chicago to San Francisco?

The cheapest return found recently is $226 with Allegiant Air, 5 Jan 2027 to 13 Jan 2027, found 2 days ago. The cheapest return we hold, of any age, is $214 with Frontier Airlines, 3 Dec to 5 Dec, found 7 days ago. The cheapest return fare on each of 10 departure dates is usually $240 to $376.

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

The cheapest one-way found recently is $187 with Alaska Airlines, 10 May 2027, found 3 days ago. The cheapest one-way we hold, of any age, is $140 with Frontier Airlines, 26 Feb 2027, found 5 days ago. The cheapest one-way fare on each of 4 departure dates is usually $175 to $193.

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

December 2026 is the cheapest month for a return, from $214, 3 Dec to 5 Dec, found 7 days ago. February 2027 is the cheapest month for a one-way, from $140, 26 Feb 2027, found 5 days ago.

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

In 49 days of prices between 24 Sept and 11 Nov, return fares 30 to 59 days before departure were typically 30% lower than 0 to 6 days before departure. One-way fares were cheapest 14 to 29 days before departure.

Is there a direct flight from Chicago to San Francisco?

Yes, the cheapest nonstop return found recently is $297 with American Airlines, 5 Jan 2027 to 12 Jan 2027, found 2 days ago. The cheapest nonstop one-way found recently is $200 with Southwest Airlines, 19 Apr 2027, found 5 days ago.

Every nonstop date from Chicago to San Francisco

How long is the flight from Chicago to San Francisco?

The cheapest nonstop one-way found recently, with Southwest Airlines on 19 Apr 2027, takes 4 h 45 min from Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO). The cheapest one-way found recently, with Alaska Airlines on 10 May 2027, takes 7 h 50 min with 1 stop.

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

Between 22 Nov and 16 Apr 2027, Frontier Airlines has the cheapest return on 6 of the 10 departure dates we hold, Alaska Airlines on 3 and Allegiant Air on 1. Between 26 Feb 2027 and 10 May 2027, Alaska Airlines has the cheapest one-way on 2 of the 4 departure dates we hold, Frontier Airlines on 1 and Southwest Airlines on 1.