Cheap flights from Seattle to Chicago
The cheapest round trip from Seattle to Chicago that travelers found recently is $295 with a carry-on: a $295 fare on Southwest, which usually includes a carry-on. It leaves Fri, Dec 25 and comes back Fri, Jan 1.
Live prices for Fri, Dec 25 to Fri, Jan 1
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Fri, Dec 25 | Fri, Jan 1 | Southwest | SEA → MDW | Nonstop | $295 | Included | $295 | Live price |
| Tue, Feb 9 | Tue, Feb 16 | Alaska Airlines | SEA → ORD | Nonstop | $322 | Included | $322 | Live price |
| Wed, Nov 4 | Sun, Nov 8 | Frontier | SEA → ORD | 1 stop | $322 | +$110 | $432 | Live price |
| Thu, Nov 5 | Sun, Nov 8 | Frontier | SEA → ORD | 1 stop | $328 | +$110 | $438 | Live price |
| Tue, Nov 24 | Sat, Nov 28 | American Airlines | SEA → ORD | Nonstop | $438 | Included | $438 | 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 | Wed, Nov 4 to Sun, Nov 8, 4 nights | $432 | Live price |
| December 2026 | Fri, Dec 25 to Fri, Jan 1, 7 nights | $295 | Live price |
| February 2027 | Tue, Feb 9 to Tue, Feb 16, 7 nights | $322 | Live price |
Bag fees on this route
What the airlines flying Seattle to Chicago 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 |
| Southwest | Included | $35 |
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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