Cheap flights from Chicago to San Diego
The cheapest round trip from Chicago to San Diego that travelers found recently is $294 with a carry-on: a $294 fare on Alaska Airlines, which usually includes a carry-on. It leaves Thu, Dec 24 and comes back Mon, Dec 28.
Live prices for Thu, Dec 24 to Mon, Dec 28
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Thu, Dec 24 | Mon, Dec 28 | Alaska Airlines | ORD → SAN | Nonstop | $294 | Included | $294 | Live price |
| Sat, Nov 28 | Wed, Dec 2 | American Airlines | ORD → SAN | Nonstop | $353 | Included | $353 | Live price |
| Thu, Nov 5 | Tue, Nov 10 | Frontier | ORD → SAN | 1 stop | $264 | +$110 | $374 | 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 |
|---|---|---|---|
| November 2026 | Sat, Nov 28 to Wed, Dec 2, 4 nights | $353 | Live price |
| December 2026 | Thu, Dec 24 to Mon, Dec 28, 4 nights | $294 | Live price |
Bag fees on this route
What the airlines flying Chicago to San Diego 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 |
| American Airlines | Included | $40 |
| Frontier | $55 | $50 |
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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