New York to Chicago: what the flight costs
In the last 60 days we checked this route 9 times. The typical round trip was $364 per person and the lowest $337, taxes and fees included.
| Per person | |
|---|---|
| Lowest seen | $337 |
| Typical (median) | $364 |
| Price checks, 60 days | 9 |
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Trips we picked on this route
$363 per person, round trip, taxes and fees included
Every fare we found in the last 30 days
| Checked | Trip dates | Per person | Airline | Stops | Duration | Source |
|---|---|---|---|---|---|---|
| Oct 12, 2026 | Oct 23–25, 2026 | $497 | B6 + F9 | with a stop | 2h 54m | Kiwi.com |
| Oct 11, 2026 | Oct 23–25, 2026 | $337 | United | nonstop | 2h 48m | Google Flights |
| Oct 11, 2026 | Oct 23–25, 2026 | $337 | United | nonstop | 2h 48m | Google Flights |
| Oct 11, 2026 | Oct 16–18, 2026 | $363 | B6 | nonstop | 5h 14m | Kiwi.com |
| Oct 11, 2026 | Oct 16–18, 2026 | $363 | B6 | nonstop | 5h 14m | Kiwi.com |
| Oct 11, 2026 | Oct 23–25, 2026 | $451 | B6 + F9 | with a stop | 2h 54m | Kiwi.com |
| Oct 11, 2026 | Oct 16–18, 2026 | $364 | B6 | nonstop | 2h 54m | Kiwi.com |
| Oct 11, 2026 | Oct 23–25, 2026 | $451 | B6 + F9 | with a stop | 2h 54m | Kiwi.com |
| Oct 11, 2026 | Oct 16–18, 2026 | $364 | B6 | nonstop | 2h 54m | Kiwi.com |
About Chicago
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Chicago from every city: when to go, where to stay, what to do
Questions about New York to Chicago
What does a round trip from New York to Chicago usually cost?
Over the last 60 days the typical price we found was $364 per person, taxes and fees included, across 9 checks; the lowest was $337.
When is the best time to fly from New York to Chicago?
Chicago is at its best in May, June, July, August, September and October. Avoid December, January, February, March: Bitter cold and wind off the lake
Do I need a passport to fly from New York to Chicago?
No, a government photo ID is enough for US citizens.