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Cheap flights from Chicago to New York

The cheapest round trip from Chicago to New York that travelers found recently is $146 with a carry-on: a $146 fare on Southwest, which usually includes a carry-on. It leaves Thu, Nov 26 and comes back Tue, Dec 1.

Live prices for Thu, Nov 26 to Tue, Dec 1

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$146Cheapest round trip, carry-on included (est.)
$335Typical round trip found recently
NovemberCheapest month in the next few, from $146
55%Of these fares are nonstop

Cheapest trips travelers found recently

LeaveReturnAirlineAirportsStopsFareCarry-on (est.)TotalLive prices
Thu, Nov 26Tue, Dec 1SouthwestMDW → LGANonstop$146Included$146Live price
Sat, Nov 14Thu, Nov 26American AirlinesORD → EWRNonstop$208Included$208Live price
Tue, Oct 27Wed, Oct 28UnitedORD → EWRNonstop$224Included$224Live price
Sat, Nov 21Wed, Nov 25American AirlinesORD → LGANonstop$234Included$234Live price
Thu, Nov 12Sun, Nov 15American AirlinesORD → EWRNonstop$246Included$246Live price
Fri, Oct 23Tue, Oct 27American AirlinesORD → LGANonstop$247Included$247Live price
Mon, Mar 1Sun, Mar 7American AirlinesORD → LGANonstop$250Included$250Live price
Thu, Nov 5Sun, Nov 8UnitedORD → EWRNonstop$254Included$254Live price
Sun, Nov 22Thu, Nov 26UnitedORD → EWRNonstop$254Included$254Live price
Fri, Oct 23Sun, Oct 25FrontierORD → EWR1 stop$158+$110$268Live 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

MonthCheapest tripFromLive prices
October 2026Tue, Oct 27 to Wed, Oct 28, 1 night$224Live price
November 2026Thu, Nov 26 to Tue, Dec 1, 5 nights$146Live price
December 2026Fri, Dec 11 to Sun, Dec 13, 2 nights$268Live price
March 2027Mon, Mar 1 to Sun, Mar 7, 6 nights$250Live price
April 2027Fri, Apr 16 to Sun, Apr 18, 2 nights$328Live price
May 2027Sat, May 1 to Tue, May 4, 3 nights$335Live price

Bag fees on this route

What the airlines flying Chicago to New York 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.

AirlineCarry-on, each wayChecked bag, each way
American AirlinesIncluded$40
Frontier$55$50
SouthwestIncluded$35
UnitedIncluded$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).

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