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Chicago to New York in October 2026 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 October 2026, the cheapest return found recently is $286 with Frontier Airlines, 21 Oct – 23 Oct, found yesterday. The cheapest one-way found recently is $134 with Frontier Airlines, 20 Oct, found 3 days ago.

Return

In October 2026, the cheapest return fare on each of 9 departure dates is usually $276 to $306. Across all 33 departure dates we hold on this route, it is usually $252 to $306. Of the 3 months with enough return fares to compare, 1 is usually cheaper than October 2026.

Cheapest return found recently

$286

21 Oct – 23 Oct · Frontier Airlines

O'Hare International Airport (ORD) → LaGuardia Airport (LGA)

out 1 stop, back 1 stop

found yesterday

See prices for these datesCheck today's price

Cheapest we hold, of any age

$250

31 Oct – 3 Nov · Frontier Airlines

Chicago Midway International Airport (MDW) → LaGuardia Airport (LGA)

out 1 stop, back 1 stop

found 2 days ago

See prices for these datesCheck today's price

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The cheapest dates in October 2026

DatesFromAirlineStopsFound
31 Oct – 3 Nov$250Frontier Airlinesout 1 stop, back 1 stopfound 2 days agoSee prices for these dates
29 Oct – 9 Nov$276Frontier Airlinesout 1 stop, back 1 stopfound 5 days agoSee prices for these dates
30 Oct – 9 Nov$276Frontier Airlinesout 1 stop, back 1 stopfound 5 days agoSee prices for these dates
21 Oct – 23 Oct$286Frontier Airlinesout 1 stop, back 1 stopfound yesterdaySee prices for these dates
27 Oct – 30 Oct$287Frontier Airlinesout 1 stop, back 1 stopfound todaySee prices for these dates

Every date we hold

9 departure dates

20 Oct – 23 Oct: $306, found 2 days ago21 Oct – 23 Oct: $286, found yesterday22 Oct – 4 Nov: $302, found yesterday24 Oct – 25 Oct: $331, found 5 days ago25 Oct – 26 Oct: $387, found yesterday27 Oct – 30 Oct: $287, found today29 Oct – 9 Nov: $276, found 5 days ago30 Oct – 9 Nov: $276, found 5 days ago31 Oct – 3 Nov: $250, found 2 days agoOct
See the chart as a table
The cheapest price seen for each departure date — per traveler in Economy.
DatesFromAirlineAirportsStopsFound
20 Oct – 23 Oct$306Frontier AirlinesO'Hare International Airport (ORD) → LaGuardia Airport (LGA)out 1 stop, back nonstopfound 2 days agoSee prices for these dates
21 Oct – 23 Oct$286Frontier AirlinesO'Hare International Airport (ORD) → LaGuardia Airport (LGA)out 1 stop, back 1 stopfound yesterdaySee prices for these dates
22 Oct – 4 Nov$302Frontier AirlinesO'Hare International Airport (ORD) → Newark Liberty International Airport (EWR)out 1 stop, back 1 stopfound yesterdaySee prices for these dates
24 Oct – 25 Oct$331Frontier AirlinesO'Hare International Airport (ORD) → LaGuardia Airport (LGA)out 1 stop, back 1 stopfound 5 days agoSee prices for these dates
25 Oct – 26 Oct$387American AirlinesO'Hare International Airport (ORD) → Newark Liberty International Airport (EWR)out nonstop, back nonstopfound yesterdaySee prices for these dates
27 Oct – 30 Oct$287Frontier AirlinesChicago Midway International Airport (MDW) → LaGuardia Airport (LGA)out 1 stop, back 1 stopfound todaySee prices for these dates
29 Oct – 9 Nov$276Frontier AirlinesChicago Midway International Airport (MDW) → LaGuardia Airport (LGA)out 1 stop, back 1 stopfound 5 days agoSee prices for these dates
30 Oct – 9 Nov$276Frontier AirlinesO'Hare International Airport (ORD) → LaGuardia Airport (LGA)out 1 stop, back 1 stopfound 5 days agoSee prices for these dates
31 Oct – 3 Nov$250Frontier AirlinesChicago Midway International Airport (MDW) → LaGuardia Airport (LGA)out 1 stop, back 1 stopfound 2 days agoSee prices for these dates

Which month looks cheapest?

November 2026 is the cheapest month — from $223.

October 2026From $2509 departure dates31 Oct – 3 Nov · found 2 days agoSee prices for these dates
November 2026From $223Cheapest seen14 departure dates26 Nov – 1 Dec · found 18 hours agoSee prices for these datesEvery date in November 2026
December 2026From $2327 departure dates22 Dec – 26 Dec · found 3 days agoSee prices for these datesEvery date in December 2026
March 2027From $3221 departure date9 Mar 2027 – 11 Mar 2027 · found 2 days agoSee prices for these dates
April 2027From $3232 departure dates4 Apr 2027 – 6 Apr 2027 · found 5 days agoSee prices for these dates

One-way

In October 2026, the cheapest one-way fare on each of 4 departure dates is usually $152 to $169. Across all 27 departure dates we hold on this route, it is usually $132 to $168. Of the 5 months with enough one-way fares to compare, 2 are usually cheaper than October 2026.

Cheapest one-way found recently

$134

20 Oct · Frontier Airlines

O'Hare International Airport (ORD) → LaGuardia Airport (LGA)

1 stop

found 3 days ago

Open this tripCheck today's price

It is also the cheapest one-way we hold, of any age.

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The cheapest dates in October 2026

DatesFromAirlineStopsFound
20 Oct$134Frontier Airlines1 stopfound 3 days agoOpen this trip
23 Oct$158American Airlinesnonstopfound 6 days agoOpen this trip
25 Oct$163Southwest Airlinesnonstopfound 4 days agoOpen this trip
28 Oct$186Allegiant Air1 stopfound 5 days agoOpen this trip

Every date we hold

4 departure dates

20 Oct: $134, found 3 days ago23 Oct: $158, found 6 days ago25 Oct: $163, found 4 days ago28 Oct: $186, found 5 days agoOct
See the chart as a table
The cheapest price seen for each departure date — per traveler in Economy.
DatesFromAirlineAirportsStopsFound
20 Oct$134Frontier AirlinesO'Hare International Airport (ORD) → LaGuardia Airport (LGA)1 stopfound 3 days agoOpen this trip
23 Oct$158American AirlinesO'Hare International Airport (ORD) → LaGuardia Airport (LGA)nonstopfound 6 days agoOpen this trip
25 Oct$163Southwest AirlinesChicago Midway International Airport (MDW) → LaGuardia Airport (LGA)nonstopfound 4 days agoOpen this trip
28 Oct$186Allegiant AirChicago Rockford International Airport (RFD) → Newark Liberty International Airport (EWR)1 stopfound 5 days agoOpen this trip

Which month looks cheapest?

November 2026 is the cheapest month — from $102.

October 2026From $1344 departure dates20 Oct · found 3 days agoOpen this trip
November 2026From $102Cheapest seen7 departure dates11 Nov · found yesterdayOpen this tripEvery date in November 2026
December 2026From $1156 departure dates2 Dec · found yesterdayOpen this tripEvery date in December 2026
February 2027From $1241 departure date8 Feb 2027 · found 3 days agoOpen this trip
March 2027From $1743 departure dates22 Mar 2027 · found yesterdayOpen this trip
April 2027From $1301 departure date12 Apr 2027 · found 5 days agoOpen this trip
July 2027From $1625 departure dates17 Jul 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