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Chicago to San Francisco flights

The cheapest round trip we found from Chicago to San Francisco is $283 (Dec 25 – 31, 1 stop), 16% below the usual $336.

CHI to SFO · Round trip · Economy · Prices per person in USD · Price found (3 days ago)

Cheapest found

$283 16% less
Dec 25 – 31 · 1 stop · Usually $336
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Good price — book if the dates work 16% below the usual $336. Based on 44 days of prices.
Not ready to book? We'll email you when Chicago → San Francisco drops below $265.
Dec – Jan · 5–7 nights · Change

Cheapest round trip by month

Lowest fare found per departure month
Cheapest month Below usual Usual price $336
Cheapest round trip from Chicago to San Francisco by departure month
MonthCheapest round trip
November 2026$376
December 2026$283
January 2027$226 (cheapest month)
February 2027$303
March 2027No fares found yet
April 2027$368
May 2027$381

Cheapest dates in the next 4 months

Round trip, per person
  • Dec 25 – 31 6 nights · leave Fri
    $283 −16% vs usual
    Frontier Airlines 1 stop · 6h 19m
    Book
  • Dec 25 – 30 5 nights · leave Fri
    $286 −15% vs usual
    Frontier Airlines 1 stop · 6h 19m
    Book
  • Feb 9 – 13, 2027 4 nights · leave Tue
    $303 −10% vs usual
    Frontier Airlines 1 stop · 5h 55m
    Book
  • Dec 2 – 5 3 nights · leave Wed
    $311 −7% vs usual
    Frontier Airlines 1 stop · 6h 28m
    Book
  • Feb 10 – 13, 2027 3 nights · leave Wed
    $340
    Frontier Airlines 1 stop · 5h 45m
    Book
  • Nov 19 – 21 2 nights · leave Thu
    $380 +13% vs usual
    Frontier Airlines 1 stop · 5h 52m
    Book
  • Nov 25 – 30 5 nights · leave Wed
    $399 +19% vs usual
    Frontier Airlines 1 stop · 7h 51m
    Book
  • Nov 25 – 29 4 nights · leave Wed
    $520 +55% vs usual
    Frontier Airlines 1 stop · 7h 51m
    Book

Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert

Things to do in San Francisco

One Go City pass for Golden Gate Bay Cruise, Exploratorium, Filoli and more

More things to do in San Francisco →

Go City prices checked Oct 23, 2026; the final price is on Go City. Partner links: we may earn a commission if you book, at no extra cost to you.

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San Francisco · Dec 25 – 31

Airport transfer · Kiwitaxi

Partner links: we may earn a commission if you book, at no extra cost to you.

Good to know

Airline Frontier Airlines Every cheap fare we track on this route is on Frontier Airlines.
Most expensive month May Cheapest round trip that month is $381, vs $226 in the cheapest month.

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Flights to San Francisco from other cities

All flights to San Francisco Flying the other way? San Francisco to Chicago from $268

Chicago to San Francisco: questions

How much does a flight from Chicago to San Francisco cost?

The cheapest round trip we have found right now is $283, leaving December 25 and returning December 31. The usual price on this route is about $336, so this fare is 16% less. Prices are per person, economy, in USD.

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

January 2027, with round trips from $226. The most expensive month in our data is May (from $381). Based on the 6 months ahead we have prices for.

Which airports do Chicago to San Francisco flights use?

Chicago airports include O'Hare International (ORD), Chicago Midway International (MDW) and Chicago Rockford International (RFD). San Francisco airports include San Francisco International (SFO). The prices on this page cover every airport in both cities (CHI and SFO are the city codes).

About this route

We track round-trip economy fares from Chicago (United States) to San Francisco (United States) using Travelpayouts / Aviasales data. The cheapest round trip we've found is $283, departing December 25 and returning December 31, about 16% below the usual $336. Right now we're following 8 upcoming date combinations on this route. The cheapest month to fly in our data is January, from $226. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.

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