Logan International (BOS) to O'Hare International (ORD).
| Departure | Return | Price |
|---|---|---|
| 05/23/2026 | 05/30/2026 | $177 |
| 05/21/2026 | 05/30/2026 | $182 |
| 05/23/2026 | 05/28/2026 | $182 |
| 05/23/2026 | 05/29/2026 | $182 |
| 05/24/2026 | 05/30/2026 | $182 |
| 05/25/2026 | 05/30/2026 | $182 |
| 05/28/2026 | 06/02/2026 | $182 |
| 05/28/2026 | 06/03/2026 | $182 |
| 05/29/2026 | 06/03/2026 | $182 |
| 05/30/2026 | 06/04/2026 | $182 |
Based on current fares, May is the cheapest month to fly from Boston to Chicago, with average fares around $185 round trip (as low as $177).
See the full month-by-month and day-of-week price analysis
Best Time to Fly BOS → ORDDeparture date prices (economy, round trip). Green = cheap, red = expensive.
The cheapest month to fly from Boston to Chicago is May, with average round-trip fares around $185. Fares in May start as low as $177. The most expensive month is August, averaging $200.
A nonstop flight from Boston to Chicago takes approximately 2h 30m.
The cheapest flight from Boston to Chicago currently starts at $177 round trip in economy class.
The average round-trip flight price from Boston to Chicago is $202 in economy class.
The distance is 867 miles (1395 km). with a nonstop flight time of about 2h 30m. The lowest fare currently available is $177 departing in May. The average round-trip fare is $202.
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