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Chicago to New York flights in December 2026 from $248 MDW, ORD, RFD → EWR, JFK, LGA

Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD) → Newark Liberty International Airport (EWR), John F. Kennedy International Airport (JFK), LaGuardia Airport (LGA)

For departures in December 2026, the cheapest return found recently is $248 with Frontier Airlines, 5 Dec – 8 Dec, found 2 days ago. The cheapest one-way found recently is $277 with Allegiant Air, 8 Dec, found 2 days ago.

Return

In December 2026, the cheapest return fare on each of 13 departure dates is usually $248 to $329. Across all 37 departure dates we hold on this route, it is usually $268 to $345. Of the 7 months with enough return fares to compare, 2 are usually cheaper than December 2026.

Cheapest return found recently

$248

5 Dec – 8 Dec · Frontier Airlines

O'Hare International Airport (ORD) → Newark Liberty International Airport (EWR)

out 1 stop, back 1 stop

found 2 days ago

See prices for these datesCheck today's price

Cheapest we hold, of any age

$236

8 Dec – 11 Dec · Frontier Airlines

O'Hare International Airport (ORD) → Newark Liberty International Airport (EWR)

out 1 stop, back 1 stop

found 5 days ago

See prices for these datesCheck today's price

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The cheapest dates in December 2026

DatesFromAirlineStopsFound
8 Dec – 11 Dec$236Frontier Airlinesout 1 stop, back 1 stopfound 5 days agoSee prices for these dates
9 Dec – 11 Dec$240Frontier Airlinesout 1 stop, back 1 stopfound 7 days agoSee prices for these dates
24 Dec – 28 Dec$243United Airlinesout nonstop, back nonstopfound 5 days agoSee prices for these dates
5 Dec – 8 Dec$248Frontier Airlinesout 1 stop, back 1 stopfound 2 days agoSee prices for these dates
4 Dec – 9 Dec$255Frontier Airlinesout 1 stop, back 1 stopfound 5 days agoSee prices for these dates

Every date we hold

13 departure dates

4 Dec – 9 Dec: $255, found 5 days ago5 Dec – 8 Dec: $248, found 2 days ago8 Dec – 11 Dec: $236, found 5 days ago9 Dec – 11 Dec: $240, found 7 days ago11 Dec – 11 Dec: $333, found 3 days ago13 Dec – 19 Dec: $317, found 4 days ago14 Dec – 20 Dec: $329, found 4 days ago18 Dec – 20 Dec: $314, found 5 days ago22 Dec – 29 Dec: $295, found 4 days ago23 Dec – 26 Dec: $292, found 5 days ago24 Dec – 28 Dec: $243, found 5 days ago28 Dec – 31 Dec: $345, found 7 days ago31 Dec – 3 Jan 2027: $348, found 7 days agoDec
See the chart as a table
The cheapest price seen for each departure date — per traveler in Economy.
DatesFromAirlineAirportsStopsFound
4 Dec – 9 Dec$255Frontier AirlinesChicago Midway International Airport (MDW) → Newark Liberty International Airport (EWR)out 1 stop, back 1 stopfound 5 days agoSee prices for these dates
5 Dec – 8 Dec$248Frontier AirlinesO'Hare International Airport (ORD) → Newark Liberty International Airport (EWR)out 1 stop, back 1 stopfound 2 days agoSee prices for these dates
8 Dec – 11 Dec$236Frontier AirlinesO'Hare International Airport (ORD) → Newark Liberty International Airport (EWR)out 1 stop, back 1 stopfound 5 days agoSee prices for these dates
9 Dec – 11 Dec$240Frontier AirlinesChicago Midway International Airport (MDW) → Newark Liberty International Airport (EWR)out 1 stop, back 1 stopfound 7 days agoSee prices for these dates
11 Dec – 11 Dec$333United AirlinesO'Hare International Airport (ORD) → Newark Liberty International Airport (EWR)out nonstop, back nonstopfound 3 days agoSee prices for these dates
13 Dec – 19 Dec$317American AirlinesO'Hare International Airport (ORD) → John F. Kennedy International Airport (JFK)out nonstop, back nonstopfound 4 days agoSee prices for these dates
14 Dec – 20 Dec$329Frontier AirlinesO'Hare International Airport (ORD) → Newark Liberty International Airport (EWR)out 1 stop, back nonstopfound 4 days agoSee prices for these dates
18 Dec – 20 Dec$314American AirlinesO'Hare International Airport (ORD) → LaGuardia Airport (LGA)out nonstop, back nonstopfound 5 days agoSee prices for these dates
22 Dec – 29 Dec$295United AirlinesO'Hare International Airport (ORD) → Newark Liberty International Airport (EWR)out nonstop, back nonstopfound 4 days agoSee prices for these dates
23 Dec – 26 Dec$292United AirlinesO'Hare International Airport (ORD) → Newark Liberty International Airport (EWR)out nonstop, back nonstopfound 5 days agoSee prices for these dates
24 Dec – 28 Dec$243United AirlinesO'Hare International Airport (ORD) → Newark Liberty International Airport (EWR)out nonstop, back nonstopfound 5 days agoSee prices for these dates
28 Dec – 31 Dec$345Frontier AirlinesO'Hare International Airport (ORD) → LaGuardia Airport (LGA)out 1 stop, back 1 stopfound 7 days agoSee prices for these dates
31 Dec – 3 Jan 2027$348United AirlinesO'Hare International Airport (ORD) → Newark Liberty International Airport (EWR)out nonstop, back nonstopfound 7 days agoSee prices for these dates

Which month looks cheapest?

February 2027 is the cheapest month — from $195.

November 2026From $2924 departure dates26 Nov – 2 Dec · found 7 days agoSee prices for these dates
December 2026From $23613 departure dates8 Dec – 11 Dec · found 5 days agoSee prices for these dates
January 2027From $2393 departure dates15 Jan 2027 – 19 Jan 2027 · found 6 days agoSee prices for these dates
February 2027From $195Cheapest seen4 departure dates3 Feb 2027 – 9 Feb 2027 · found yesterdaySee prices for these dates
March 2027From $3102 departure dates1 Mar 2027 – 7 Mar 2027 · found 6 days agoSee prices for these dates
April 2027From $3593 departure dates3 Apr 2027 – 6 Apr 2027 · found 5 days agoSee prices for these dates
May 2027From $3441 departure date7 May 2027 – 23 May 2027 · found 4 days agoSee prices for these dates
July 2027From $3383 departure dates21 Jul 2027 – 21 Jul 2027 · found 4 days agoSee prices for these dates
October 2027From $7304 departure dates5 Oct 2027 – 12 Oct 2027 · found 3 days agoSee prices for these dates

One-way

In December 2026, the cheapest one-way fare on each of 9 departure dates is usually $135 to $236. Across all 23 departure dates we hold on this route, it is usually $141 to $180. Of the 3 months with enough one-way fares to compare, 1 is usually cheaper than December 2026.

Cheapest one-way found recently

$277

8 Dec · Allegiant Air

Chicago Rockford International Airport (RFD) → John F. Kennedy International Airport (JFK)

2 stops

found 2 days ago

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Cheapest we hold, of any age

$103

15 Dec · Frontier Airlines

O'Hare International Airport (ORD) → Newark Liberty International Airport (EWR)

1 stop

found 4 days ago

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The cheapest dates in December 2026

DatesFromAirlineStopsFound
15 Dec$103Frontier Airlines1 stopfound 4 days agoOpen this trip
10 Dec$134Frontier Airlines1 stopfound 4 days agoOpen this trip
31 Dec$135Frontier Airlines1 stopfound 7 days agoOpen this trip
17 Dec$153Frontier Airlines1 stopfound 6 days agoOpen this trip
20 Dec$153Frontier Airlines1 stopfound 4 days agoOpen this trip

Every date we hold

9 departure dates

2 Dec: $490, found 2 days ago8 Dec: $277, found 2 days ago10 Dec: $134, found 4 days ago14 Dec: $161, found 4 days ago15 Dec: $103, found 4 days ago17 Dec: $153, found 6 days ago20 Dec: $153, found 4 days ago27 Dec: $236, found 6 days ago31 Dec: $135, found 7 days agoDec
See the chart as a table
The cheapest price seen for each departure date — per traveler in Economy.
DatesFromAirlineAirportsStopsFound
2 Dec$490Allegiant AirChicago Rockford International Airport (RFD) → LaGuardia Airport (LGA)3 stopsfound 2 days agoOpen this trip
8 Dec$277Allegiant AirChicago Rockford International Airport (RFD) → John F. Kennedy International Airport (JFK)2 stopsfound 2 days agoOpen this trip
10 Dec$134Frontier AirlinesO'Hare International Airport (ORD) → Newark Liberty International Airport (EWR)1 stopfound 4 days agoOpen this trip
14 Dec$161Allegiant AirChicago Rockford International Airport (RFD) → Newark Liberty International Airport (EWR)2 stopsfound 4 days agoOpen this trip
15 Dec$103Frontier AirlinesO'Hare International Airport (ORD) → Newark Liberty International Airport (EWR)1 stopfound 4 days agoOpen this trip
17 Dec$153Frontier AirlinesChicago Midway International Airport (MDW) → LaGuardia Airport (LGA)1 stopfound 6 days agoOpen this trip
20 Dec$153Frontier AirlinesChicago Midway International Airport (MDW) → LaGuardia Airport (LGA)1 stopfound 4 days agoOpen this trip
27 Dec$236Frontier AirlinesChicago Midway International Airport (MDW) → LaGuardia Airport (LGA)1 stopfound 6 days agoOpen this trip
31 Dec$135Frontier AirlinesChicago Midway International Airport (MDW) → Newark Liberty International Airport (EWR)1 stopfound 7 days agoOpen this trip

Which month looks cheapest?

November 2026 is the cheapest month — from $96.

November 2026From $96Cheapest seen5 departure dates19 Nov · found 2 days agoOpen this trip
December 2026From $1039 departure dates15 Dec · found 4 days agoOpen this trip
February 2027From $1082 departure dates3 Feb 2027 · found 3 days agoOpen this trip
March 2027From $1811 departure date24 Mar 2027 · found 6 days agoOpen this trip
May 2027From $1733 departure dates7 May 2027 · found 4 days agoOpen this trip
July 2027From $1801 departure date24 Jul 2027 · found 4 days agoOpen this trip
August 2027From $1661 departure date2 Aug 2027 · found 6 days agoOpen this trip
October 2027From $2251 departure date9 Oct 2027 · found 4 days agoOpen this trip

Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work