Cheap flights from Manhattan to Chicago

One-way fares from $459 · MHK → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Manhattan
Cheapest fare
$459

American Airlines · Sat, Nov 14

Cheapest month
November

from $459

Direct flights
Yes

American Airlines

Flight time
2h 04m

820 km

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Cheapest month to fly from Manhattan to Chicago

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $459

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

American Airlines
Depart07:06 Sat, Nov 14MHK → ORD 2h 04m · Direct
$459one way, per person
View deal
American Airlines
Depart07:06 Fri, Nov 13MHK → ORD 2h 04m · Direct
$483one way, per person
View deal
See every date in November 2026 →

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Where to stay, what to do and getting around, from our travel partners.

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Things to do

Things to do in ChicagoTours, attractions and day trips on Klook Explore →

Getting around

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About flights from Manhattan to Chicago

Manhattan (MHK) and Chicago (CHI) are about 820 km apart. Direct flights take around 2h 04m, and recent direct fares were with American Airlines. Over the next few months, one-way fares start from $459, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Manhattan to Chicago?

The cheapest one-way fare we've seen recently is $459 with American Airlines, departing Saturday, November 14, 2026.

What is the cheapest month to fly from Manhattan to Chicago?

November 2026 currently has the lowest fares, from $459 one way.

Are there direct flights from Manhattan to Chicago?

Yes. Recent direct fares were with American Airlines.

How long is the flight from Manhattan to Chicago?

A direct flight takes about 2h 04m. Manhattan and Chicago are around 820 km apart.

Which airlines fly from Manhattan to Chicago?

Recent fares on this route were with American Airlines.

More cheap flights from Manhattan

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