Cheap flights from Chicago to New Orleans
The cheapest round trip from Chicago to New Orleans that travelers found recently is $249 with a carry-on: a $249 fare on Southwest, which usually includes a carry-on. It leaves Mon, Oct 26 and comes back Wed, Oct 28.
Live prices for Mon, Oct 26 to Wed, Oct 28
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Mon, Oct 26 | Wed, Oct 28 | Southwest | MDW → MSY | 1 stop | $249 | Included | $249 | Live price |
| Fri, Oct 30 | Mon, Nov 2 | Southwest | MDW → MSY | 1 stop | $271 | Included | $271 | Live price |
| Fri, Oct 16 | Mon, Oct 19 | Frontier | ORD → MSY | 1 stop | $220 | +$110 | $330 | Live price |
| Thu, Apr 22 | Mon, Apr 26 | Southwest | MDW → MSY | 1 stop | $350 | Included | $350 | Live price |
| Wed, Dec 30 | Fri, Jan 1 | Frontier | ORD → MSY | 1 stop | $257 | +$110 | $367 | Live price |
| Thu, Nov 12 | Sun, Nov 15 | Frontier | ORD → MSY | 1 stop | $261 | +$110 | $371 | Live price |
| Tue, Dec 29 | Sat, Jan 2 | Frontier | ORD → MSY | 1 stop | $368 | +$110 | $478 | 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 | Mon, Oct 26 to Wed, Oct 28, 2 nights | $249 | Live price |
| November 2026 | Thu, Nov 12 to Sun, Nov 15, 3 nights | $371 | Live price |
| December 2026 | Wed, Dec 30 to Fri, Jan 1, 2 nights | $367 | Live price |
| April 2027 | Thu, Apr 22 to Mon, Apr 26, 4 nights | $350 | Live price |
Bag fees on this route
What the airlines flying Chicago to New Orleans 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 |
|---|---|---|
| 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).
Not sure where to go? Tell Dipt your budget and vibe and it finds the trip.
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