Cheap flights from Los Angeles to Chicago
The cheapest round trip from Los Angeles to Chicago that travelers found recently is $159 with a carry-on: a $159 fare on American Airlines, which usually includes a carry-on. It leaves Tue, Dec 22 and comes back Tue, Jan 5.
Live prices for Tue, Dec 22 to Tue, Jan 5
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Tue, Dec 22 | Tue, Jan 5 | American Airlines | LAX → ORD | Nonstop | $159 | Included | $159 | Live price |
| Fri, Jan 15 | Fri, Jan 22 | United | LAX → ORD | Nonstop | $164 | Included | $164 | Live price |
| Tue, Nov 10 | Thu, Nov 12 | American Airlines | LAX → ORD | Nonstop | $186 | Included | $186 | Live price |
| Wed, Nov 11 | Sun, Nov 15 | Southwest | LAX → MDW | Nonstop | $194 | Included | $194 | Live price |
| Sat, Dec 12 | Tue, Dec 15 | American Airlines | LAX → ORD | Nonstop | $205 | Included | $205 | Live price |
| Fri, Nov 6 | Sun, Nov 8 | United | LAX → ORD | Nonstop | $206 | Included | $206 | Live price |
| Mon, Nov 2 | Wed, Nov 4 | Southwest | ONT → MDW | 1 stop | $235 | Included | $235 | Live price |
| Sat, Nov 7 | Mon, Nov 9 | Southwest | LAX → MDW | 1 stop | $236 | Included | $236 | Live price |
| Fri, Oct 23 | Fri, Oct 30 | Frontier | LAX → ORD | Nonstop | $215 | +$110 | $325 | Live price |
| Wed, Nov 18 | Sun, Nov 22 | Frontier | LAX → MDW | 1 stop | $225 | +$110 | $335 | 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 Fri, Oct 30, 7 nights | $325 | Live price |
| November 2026 | Tue, Nov 10 to Thu, Nov 12, 2 nights | $186 | Live price |
| December 2026 | Tue, Dec 22 to Tue, Jan 5, 14 nights | $159 | Live price |
| January 2027 | Fri, Jan 15 to Fri, Jan 22, 7 nights | $164 | Live price |
Bag fees on this route
What the airlines flying Los Angeles 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 |
|---|---|---|
| American Airlines | Included | $40 |
| Frontier | $55 | $50 |
| Southwest | Included | $35 |
| 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).
Not sure where to go? Tell Dipt your budget and vibe and it finds the trip.
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