New York to Chicago in September 2026

Dated one-way fares from New York to Chicago in September 2026. Use the calendar to see which days are cheaper.

Lowest this month $105

Highest this month $165

Sample fare $90

Airports EWR–MDW

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September 2026 price calendar

From $105 · up to $165

Mon

Tue

Wed

Thu

Fri

Sat

Sun

1 $120 2 $111 3 $165 4 $132 5 $135 6 $127 7 $127 8 $127 9 $126 10 $134 11 $112 12 $110 13 $105 14 $138 15 $105 16 $115 17 $117 18 $124 19 $116 20 $121 21 $115 22 $110 23 $111 24 $112 25 $114 26 $116 27 $116 28 $113 29 $113 30 $110

Chicago CHI

$105

Sep 15, 1:30pm · 7h 59m · 1 stop

EWR → ORD · Frontier Airlines

Chicago CHI

$105

Sep 13, 5:55am · 18h 4m · 1 stop

EWR → ORD · Frontier Airlines

Chicago CHI

$110

Sep 22, 11:35am · 7h 48m · 1 stop

EWR → ORD · Frontier Airlines

This page is only September 2026 on the New York to Chicago route. Open the full route if you want the next months side by side.

Prices move as seats sell. Confirm the live itinerary before you book New York to Chicago in September 2026.