Cheap Flights from New York City to Chicago
No deal from New York City to Chicago has cleared our price bar yet. What we have seen on the route is below.
Across 3 months of observations from New York City to Chicago, the lowest round-trip fare we recorded was $147, in August. The typical fare was $243. August was the cheapest month we saw and October the dearest.
The most recent price we saw on this route was $211 on Frontier, seen Oct 16. It is an unverified observation and may have changed.
See every deal <a href="/from/new-york-city">from New York City</a>, <a href="/to/chicago">to Chicago</a>, or the return direction <a href="/from/chicago/to/new-york-city">Chicago to New York City</a>.
Latest price we saw: New York City to Chicago
The most recent round-trip fare our sweep found on this route. It is not verified and may have changed since the date shown.
| From | Price | Per mile | Travel dates | Airline | Seen | Check price |
|---|---|---|---|---|---|---|
| New York City (EWR) to Chicago (ORD) | $211 | 14.7¢ | Dec 7 – Dec 15 | Frontier | Oct 16 | Check price |
Price history: New York City to Chicago
What we observed by month, from our signals database. Unverified observations, not bookable prices.
| Month | Low | Typical | Sightings |
|---|---|---|---|
| Oct 2026 | $176 | $237 | 295 |
| Sep 2026 | $174 | $267 | 477 |
| Aug 2026 | $147 | $226 | 755 |
Frequently asked questions
How many flight deals from New York City to Chicago are on Sparkflights right now?
There are 0 verified deals from New York City to Chicago on the board right now. The list refreshes hourly.
What is the lowest price ever seen from New York City to Chicago?
The lowest fare we've recorded from New York City to Chicago is $147, based on 1527 price observations over 3 months.
How much does a flight from New York City to Chicago cost?
The typical round-trip fare we observed from New York City to Chicago is $243, against a recorded low of $147. These are observations, not quotes.
When is the cheapest month to fly New York City to Chicago?
August was the cheapest month we observed from New York City to Chicago and October the dearest, over 3 months of data.
What is the current price from New York City to Chicago?
The most recent fare our sweep saw from New York City to Chicago is $211, on Oct 16. It is an unverified observation rather than a verified deal, so check it before booking.