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New York to Chicago flights in December 2026 from $128 EWR, JFK, LGA → MDW, ORD, RFD

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

For departures in December 2026, the cheapest return found recently is $193 with Frontier Airlines, 2 Dec – 9 Dec, found yesterday. The cheapest one-way found recently is $128 with United Airlines, 28 Dec, found 2 days ago.

Return

In December 2026, the cheapest return fare on each of 9 departure dates is usually $327 to $372. Across all 38 departure dates we hold on this route, it is usually $317 to $363. Of the 6 months with enough return fares to compare, 3 are usually cheaper than December 2026.

Cheapest return found recently

$193

2 Dec – 9 Dec · Frontier Airlines

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

out 1 stop, back 1 stop

found yesterday

See prices for these datesCheck today's price

It is also the cheapest return we hold, of any age.

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The cheapest dates in December 2026

DatesFromAirlineStopsFound
2 Dec – 9 Dec$193Frontier Airlinesout 1 stop, back 1 stopfound yesterdaySee prices for these dates
11 Dec – 18 Dec$296Frontier Airlinesout 1 stop, back nonstopfound 4 days agoSee prices for these dates
26 Dec – 30 Dec$327Southwest Airlinesout nonstop, back nonstopfound 3 days agoSee prices for these dates
27 Dec – 15 Jan 2027$328Southwest Airlinesout nonstop, back 1 stopfound 5 days agoSee prices for these dates
20 Dec – 15 Jan 2027$349American Airlinesout nonstop, back 1 stopfound 5 days agoSee prices for these dates

Every date we hold

9 departure dates

2 Dec – 9 Dec: $193, found yesterday11 Dec – 18 Dec: $296, found 4 days ago20 Dec – 15 Jan 2027: $349, found 5 days ago22 Dec – 15 Jan 2027: $372, found 5 days ago23 Dec – 25 Dec: $427, found 2 days ago24 Dec – 27 Dec: $435, found 5 days ago26 Dec – 30 Dec: $327, found 3 days ago27 Dec – 15 Jan 2027: $328, found 5 days ago30 Dec – 3 Jan 2027: $362, found 4 days agoDec
See the chart as a table
The cheapest price seen for each departure date — per traveler in Economy.
DatesFromAirlineAirportsStopsFound
2 Dec – 9 Dec$193Frontier AirlinesNewark Liberty International Airport (EWR) → O'Hare International Airport (ORD)out 1 stop, back 1 stopfound yesterdaySee prices for these dates
11 Dec – 18 Dec$296Frontier AirlinesNewark Liberty International Airport (EWR) → Chicago Midway International Airport (MDW)out 1 stop, back nonstopfound 4 days agoSee prices for these dates
20 Dec – 15 Jan 2027$349American AirlinesLaGuardia Airport (LGA) → O'Hare International Airport (ORD)out nonstop, back 1 stopfound 5 days agoSee prices for these dates
22 Dec – 15 Jan 2027$372United AirlinesNewark Liberty International Airport (EWR) → O'Hare International Airport (ORD)out nonstop, back 1 stopfound 5 days agoSee prices for these dates
23 Dec – 25 Dec$427American AirlinesNewark Liberty International Airport (EWR) → O'Hare International Airport (ORD)out nonstop, back nonstopfound 2 days agoSee prices for these dates
24 Dec – 27 Dec$435American AirlinesNewark Liberty International Airport (EWR) → O'Hare International Airport (ORD)out nonstop, back nonstopfound 5 days agoSee prices for these dates
26 Dec – 30 Dec$327Southwest AirlinesLaGuardia Airport (LGA) → Chicago Midway International Airport (MDW)out nonstop, back nonstopfound 3 days agoSee prices for these dates
27 Dec – 15 Jan 2027$328Southwest AirlinesLaGuardia Airport (LGA) → Chicago Midway International Airport (MDW)out nonstop, back 1 stopfound 5 days agoSee prices for these dates
30 Dec – 3 Jan 2027$362Southwest AirlinesLaGuardia Airport (LGA) → Chicago Midway International Airport (MDW)out nonstop, back nonstopfound 4 days agoSee prices for these dates

Which month looks cheapest?

December 2026 is the cheapest month — from $193.

November 2026From $2547 departure dates21 Nov – 24 Nov · found 6 days agoSee prices for these datesEvery date in November 2026
December 2026From $193Cheapest seen9 departure dates2 Dec – 9 Dec · found yesterdaySee prices for these dates
January 2027From $2446 departure dates28 Jan 2027 – 1 Feb 2027 · found 4 days agoSee prices for these dates
February 2027From $2621 departure date16 Feb 2027 – 19 Feb 2027 · found 6 days agoSee prices for these dates
March 2027From $3592 departure dates4 Mar 2027 – 7 Mar 2027 · found 6 days agoSee prices for these dates
April 2027From $3323 departure dates25 Apr 2027 – 26 Apr 2027 · found 6 days agoSee prices for these dates
May 2027From $3591 departure date4 May 2027 – 6 May 2027 · found 6 days agoSee prices for these dates
June 2027From $3331 departure date6 Jun 2027 – 9 Jun 2027 · found 7 days agoSee prices for these dates
July 2027From $3443 departure dates19 Jul 2027 – 21 Jul 2027 · found 4 days agoSee prices for these dates
September 2027From $3584 departure dates24 Sept 2027 – 26 Sept 2027 · found 3 days agoSee prices for these dates
October 2027From $8201 departure date9 Oct 2027 – 17 Oct 2027 · found 4 days agoSee prices for these dates

One-way

In December 2026, the cheapest one-way fare on each of 8 departure dates is usually $129 to $161. Across all 23 departure dates we hold on this route, it is usually $126 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

$128

28 Dec · United Airlines

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

nonstop

found 2 days ago

Open this tripCheck today's price

Cheapest we hold, of any age

$127

25 Dec · United Airlines

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

nonstop

found 3 days ago

Open this tripCheck today's price

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The cheapest dates in December 2026

DatesFromAirlineStopsFound
25 Dec$127United Airlinesnonstopfound 3 days agoOpen this trip
28 Dec$128United Airlinesnonstopfound 2 days agoOpen this trip
27 Dec$129United Airlinesnonstopfound 7 days agoOpen this trip
13 Dec$135Frontier Airlines1 stopfound 2 days agoOpen this trip
6 Dec$140Frontier Airlines1 stopfound 3 days agoOpen this trip

Every date we hold

8 departure dates

6 Dec: $140, found 3 days ago11 Dec: $156, found 3 days ago13 Dec: $135, found 2 days ago22 Dec: $197, found 5 days ago24 Dec: $177, found 5 days ago25 Dec: $127, found 3 days ago27 Dec: $129, found 7 days ago28 Dec: $128, found 2 days agoDec
See the chart as a table
The cheapest price seen for each departure date — per traveler in Economy.
DatesFromAirlineAirportsStopsFound
6 Dec$140Frontier AirlinesNewark Liberty International Airport (EWR) → O'Hare International Airport (ORD)1 stopfound 3 days agoOpen this trip
11 Dec$156American AirlinesJohn F. Kennedy International Airport (JFK) → O'Hare International Airport (ORD)nonstopfound 3 days agoOpen this trip
13 Dec$135Frontier AirlinesLaGuardia Airport (LGA) → Chicago Midway International Airport (MDW)1 stopfound 2 days agoOpen this trip
22 Dec$197American AirlinesLaGuardia Airport (LGA) → O'Hare International Airport (ORD)nonstopfound 5 days agoOpen this trip
24 Dec$177American AirlinesLaGuardia Airport (LGA) → O'Hare International Airport (ORD)nonstopfound 5 days agoOpen this trip
25 Dec$127United AirlinesNewark Liberty International Airport (EWR) → O'Hare International Airport (ORD)nonstopfound 3 days agoOpen this trip
27 Dec$129United AirlinesNewark Liberty International Airport (EWR) → O'Hare International Airport (ORD)nonstopfound 7 days agoOpen this trip
28 Dec$128United AirlinesNewark Liberty International Airport (EWR) → O'Hare International Airport (ORD)nonstopfound 2 days agoOpen this trip

Which month looks cheapest?

November 2026 is the cheapest month — from $99.

November 2026From $99Cheapest seen3 departure dates15 Nov · found 8 days agoSee prices for these datesEvery date in November 2026
December 2026From $1278 departure dates25 Dec · found 3 days agoOpen this trip
January 2027From $1212 departure dates10 Jan 2027 · found 6 days agoOpen this trip
February 2027From $1142 departure dates17 Feb 2027 · found 4 days agoOpen this trip
April 2027From $1664 departure dates19 Apr 2027 · found 7 days agoOpen this trip
May 2027From $1802 departure dates5 May 2027 · found 4 days agoOpen this trip
September 2027From $1891 departure date1 Sept 2027 · found 3 days agoOpen this trip
October 2027From $2261 departure date9 Oct 2027 · found 2 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