May is the cheapest month to fly this route, with average fares around $188 round trip.
Average round-trip fares by departure month, based on current availability.
| Month | Avg Price | Lowest | Relative Cost | |
|---|---|---|---|---|
| May 2026 | $188 | $177 | Best | |
| June 2026 | $200 | $187 | Peak | |
| July 2026 | $198 | $190 | ||
| August 2026 | $198 | $190 |
Departing on Tuesday offers the lowest average fares at $192. Monday departures are the most expensive at $204, a difference of $12.
The best time to fly is May. Set up an alert and we'll notify you when prices drop.
Get Started Free →The cheapest month to fly from Chicago to Boston is May, with average round-trip fares around $188. The lowest fare found in May is $177.
Tuesday departures are the cheapest, averaging $192 round trip. The most expensive day is Monday at $204.
Based on current pricing trends, booking for May travel offers the best value. Avoid June if possible, as fares average $200 compared to $188 in the cheapest month. August is a solid middle-ground option at $198.
Flying in May instead of June can save you approximately $12 per round trip. The cheapest month averages $188 while the most expensive averages $200.
Airlines, flight times, price calendar, and more for Chicago to Boston
View ORD → BOS Details