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New York to Chicago flights in November 2026 from $113 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 November 2026, the cheapest return found recently is $316 with Frontier Airlines, 18 Nov – 20 Nov, found 3 days ago. The cheapest one-way found recently is $113 with American Airlines, 21 Nov, found 2 days ago.

Return

In November 2026, the cheapest return fare on each of 7 departure dates is usually $292 to $358. 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, 1 is usually cheaper than November 2026.

Cheapest return found recently

$316

18 Nov – 20 Nov · Frontier Airlines

Newark Liberty International Airport (EWR) → Chicago Midway International Airport (MDW)

out 1 stop, back 1 stop

found 3 days ago

See prices for these datesCheck today's price

Cheapest we hold, of any age

$254

21 Nov – 24 Nov · Frontier Airlines

Newark Liberty International Airport (EWR) → Chicago Midway International Airport (MDW)

out 1 stop, back 1 stop

found 6 days ago

See prices for these datesCheck today's price

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The cheapest dates in November 2026

DatesFromAirlineStopsFound
21 Nov – 24 Nov$254Frontier Airlinesout 1 stop, back 1 stopfound 6 days agoSee prices for these dates
23 Nov – 3 Dec$268Frontier Airlinesout 1 stop, back 1 stopfound 7 days agoSee prices for these dates
18 Nov – 20 Nov$316Frontier Airlinesout 1 stop, back 1 stopfound 3 days agoSee prices for these dates
19 Nov – 3 Dec$334Frontier Airlinesout 1 stop, back 1 stopfound 7 days agoSee prices for these dates
15 Nov – 17 Nov$339Frontier Airlinesout 1 stop, back 1 stopfound 6 days agoSee prices for these dates

Every date we hold

7 departure dates

13 Nov – 19 Nov: $438, found 4 days ago15 Nov – 17 Nov: $339, found 6 days ago18 Nov – 20 Nov: $316, found 3 days ago19 Nov – 3 Dec: $334, found 7 days ago21 Nov – 24 Nov: $254, found 6 days ago23 Nov – 3 Dec: $268, found 7 days ago24 Nov – 28 Nov: $377, found 6 days agoNov
See the chart as a table
The cheapest price seen for each departure date — per traveler in Economy.
DatesFromAirlineAirportsStopsFound
13 Nov – 19 Nov$438Frontier AirlinesLaGuardia Airport (LGA) → Chicago Midway International Airport (MDW)out 1 stop, back 1 stopfound 4 days agoSee prices for these dates
15 Nov – 17 Nov$339Frontier AirlinesLaGuardia Airport (LGA) → Chicago Midway International Airport (MDW)out 1 stop, back 1 stopfound 6 days agoSee prices for these dates
18 Nov – 20 Nov$316Frontier AirlinesNewark Liberty International Airport (EWR) → Chicago Midway International Airport (MDW)out 1 stop, back 1 stopfound 3 days agoSee prices for these dates
19 Nov – 3 Dec$334Frontier AirlinesNewark Liberty International Airport (EWR) → Chicago Midway International Airport (MDW)out 1 stop, back 1 stopfound 7 days agoSee prices for these dates
21 Nov – 24 Nov$254Frontier AirlinesNewark Liberty International Airport (EWR) → Chicago Midway International Airport (MDW)out 1 stop, back 1 stopfound 6 days agoSee prices for these dates
23 Nov – 3 Dec$268Frontier AirlinesNewark Liberty International Airport (EWR) → O'Hare International Airport (ORD)out 1 stop, back 1 stopfound 7 days agoSee prices for these dates
24 Nov – 28 Nov$377United AirlinesLaGuardia Airport (LGA) → O'Hare International Airport (ORD)out nonstop, back nonstopfound 6 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 dates
December 2026From $193Cheapest seen9 departure dates2 Dec – 9 Dec · found yesterdaySee prices for these datesEvery date in December 2026
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 November 2026, the cheapest one-way fare on each of 3 departure dates is usually $106 to $115. 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, November 2026 is usually the cheapest.

Cheapest one-way found recently

$113

21 Nov · American 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

$99

15 Nov · American Airlines

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

nonstop

found 8 days ago

See prices for these datesCheck today's price

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The cheapest dates in November 2026

DatesFromAirlineStopsFound
15 Nov$99American Airlinesnonstopfound 8 days agoSee prices for these dates
21 Nov$113American Airlinesnonstopfound 2 days agoOpen this trip
17 Nov$116American Airlinesnonstopfound 2 days agoOpen this trip

Every date we hold

3 departure dates

15 Nov: $99, found 8 days ago17 Nov: $116, found 2 days ago21 Nov: $113, found 2 days agoNov
See the chart as a table
The cheapest price seen for each departure date — per traveler in Economy.
DatesFromAirlineAirportsStopsFound
15 Nov$99American AirlinesNewark Liberty International Airport (EWR) → O'Hare International Airport (ORD)nonstopfound 8 days agoSee prices for these dates
17 Nov$116American AirlinesNewark Liberty International Airport (EWR) → O'Hare International Airport (ORD)nonstopfound 2 days agoOpen this trip
21 Nov$113American 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 dates
December 2026From $1278 departure dates25 Dec · found 3 days agoOpen this tripEvery date in December 2026
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