Cheap Flights from Chicago to Boston
No deal from Chicago to Boston has cleared our price bar yet. What we have seen on the route is below.
Across 3 months of observations from Chicago to Boston, the lowest round-trip fare we recorded was $156, in August. The typical fare was $316. August was the cheapest month we saw and October the dearest.
The most recent price we saw on this route was $285 on Frontier and Southwest, seen Oct 16. It is an unverified observation and may have changed.
See every deal <a href="/from/chicago">from Chicago</a>, <a href="/to/boston">to Boston</a>, or the return direction <a href="/from/boston/to/chicago">Boston to Chicago</a>.
Latest price we saw: Chicago to Boston
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 |
|---|---|---|---|---|---|---|
| Chicago (MDW) to Boston (BOS) | $285 | 16.6¢ | Dec 31 – Jan 8 | Frontier and Southwest | Oct 16 | Check price |
Price history: Chicago to Boston
What we observed by month, from our signals database. Unverified observations, not bookable prices.
| Month | Low | Typical | Sightings |
|---|---|---|---|
| Oct 2026 | $192 | $367 | 142 |
| Sep 2026 | $180 | $295 | 53 |
| Aug 2026 | $156 | $286 | 227 |
Frequently asked questions
How many flight deals from Chicago to Boston are on Sparkflights right now?
There are 0 verified deals from Chicago to Boston on the board right now. The list refreshes hourly.
What is the lowest price ever seen from Chicago to Boston?
The lowest fare we've recorded from Chicago to Boston is $156, based on 422 price observations over 3 months.
How much does a flight from Chicago to Boston cost?
The typical round-trip fare we observed from Chicago to Boston is $316, against a recorded low of $156. These are observations, not quotes.
When is the cheapest month to fly Chicago to Boston?
August was the cheapest month we observed from Chicago to Boston and October the dearest, over 3 months of data.
What is the current price from Chicago to Boston?
The most recent fare our sweep saw from Chicago to Boston is $285, on Oct 16. It is an unverified observation rather than a verified deal, so check it before booking.