Cheap flights from Chicago to San Francisco
The cheapest round trip from Chicago to San Francisco that travelers found recently is $263 with a carry-on: a $263 fare on United, which usually includes a carry-on. It leaves Wed, Nov 25 and comes back Mon, Dec 7.
Live prices for Wed, Nov 25 to Mon, Dec 7
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Wed, Nov 25 | Mon, Dec 7 | United | ORD → SFO | Nonstop | $263 | Included | $263 | Live price |
| Wed, Apr 14 | Sun, Apr 18 | Alaska Airlines | ORD → SFO | 1 stop | $349 | Included | $349 | Live price |
| Fri, Apr 16 | Sat, Apr 17 | Alaska Airlines | ORD → SJC | 1 stop | $350 | Included | $350 | Live price |
| Fri, Apr 16 | Sun, Apr 18 | Alaska Airlines | ORD → SJC | 1 stop | $350 | Included | $350 | Live price |
| Sun, Apr 18 | Sun, Apr 25 | Alaska Airlines | ORD → SJC | 1 stop | $353 | Included | $353 | Live price |
| Thu, Apr 15 | Sun, Apr 18 | Alaska Airlines | ORD → SJC | 1 stop | $354 | Included | $354 | Live price |
| Fri, Nov 13 | Mon, Nov 16 | Frontier | ORD → SFO | 1 stop | $266 | +$110 | $376 | Live price |
| Wed, Nov 18 | Sat, Nov 21 | Frontier | ORD → SFO | 1 stop | $271 | +$110 | $381 | Live price |
| Wed, Nov 18 | Fri, Nov 20 | Frontier | ORD → SFO | 1 stop | $337 | +$110 | $447 | Live price |
| Sun, Nov 8 | Fri, Nov 20 | Frontier | ORD → SFO | 1 stop | $391 | +$110 | $501 | Live price |
Round-trip prices per person, from real fares travelers found in the last few days. Carry-on fees are our estimate for each airline, both ways. Prices change fast: check the live price before you book.
Cheapest month to fly
| Month | Cheapest trip | From | Live prices |
|---|---|---|---|
| October 2026 | Fri, Oct 23 to Sun, Oct 25, 2 nights | $521 | Live price |
| November 2026 | Wed, Nov 25 to Mon, Dec 7, 12 nights | $263 | Live price |
| April 2027 | Wed, Apr 14 to Sun, Apr 18, 4 nights | $349 | Live price |
Bag fees on this route
What the airlines flying Chicago to San Francisco usually charge for one bag each way. Budget airlines often sell the cheapest fares and charge the most for bags, so compare the total, not the fare.
| Airline | Carry-on, each way | Checked bag, each way |
|---|---|---|
| Alaska Airlines | Included | $40 |
| Frontier | $55 | $50 |
| United | Included | $40 |
Our estimates: fees depend on the fare type and when you pay. Check the airline's own price when you book.
How these prices work
These are real round-trip fares that travelers found on Aviasales recently, not a live search, so they can change or sell out. Dipt adds an estimate of each airline's carry-on fee, so a cheap fare with expensive bags doesn't look cheaper than it is. "Live price" opens Dipt's live flight search for those dates, where you book with the airline or travel site you pick. Dipt may earn a commission when you book, at no extra cost to you (how Dipt makes money).
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