Cheap flights from New York to Chicago
The cheapest round trip from New York to Chicago that travelers found recently is $184 with a carry-on: a $184 fare on Southwest, which usually includes a carry-on. It leaves Tue, Nov 17 and comes back Thu, Nov 19.
Live prices for Tue, Nov 17 to Thu, Nov 19
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Tue, Nov 17 | Thu, Nov 19 | Southwest | LGA → MDW | Nonstop | $184 | Included | $184 | Live price |
| Thu, Nov 26 | Wed, Dec 2 | Southwest | LGA → MDW | Nonstop | $207 | Included | $207 | Live price |
| Thu, Nov 26 | Tue, Dec 1 | United | EWR → ORD | Nonstop | $214 | Included | $214 | Live price |
| Tue, Nov 10 | Fri, Nov 13 | JetBlue | JFK → ORD | 1 stop | $218 | Included | $218 | Live price |
| Mon, Jan 11 | Sun, Jan 17 | United | LGA → ORD | Nonstop | $239 | Included | $239 | Live price |
| Tue, Nov 24 | Mon, Nov 30 | Southwest | LGA → MDW | 1 stop | $242 | Included | $242 | Live price |
| Mon, Dec 14 | Mon, Dec 21 | Southwest | LGA → MDW | Nonstop | $247 | Included | $247 | Live price |
| Thu, Nov 5 | Sun, Nov 8 | United | EWR → ORD | Nonstop | $254 | Included | $254 | Live price |
| Fri, Nov 27 | Wed, Dec 2 | American Airlines | LGA → ORD | Nonstop | $262 | Included | $262 | Live price |
| Fri, Apr 23 | Sun, Apr 25 | United | EWR → ORD | Nonstop | $270 | Included | $270 | 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 30 to Mon, Nov 2, 3 nights | $289 | Live price |
| November 2026 | Tue, Nov 17 to Thu, Nov 19, 2 nights | $184 | Live price |
| December 2026 | Mon, Dec 14 to Mon, Dec 21, 7 nights | $247 | Live price |
| January 2027 | Mon, Jan 11 to Sun, Jan 17, 6 nights | $239 | Live price |
| April 2027 | Fri, Apr 23 to Sun, Apr 25, 2 nights | $270 | Live price |
| June 2027 | Sun, Jun 6 to Wed, Jun 9, 3 nights | $327 | Live price |
Bag fees on this route
What the airlines flying New York 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 |
| JetBlue | Included | $40 |
| 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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