$94 Find Cheap Flights from Chicago to Massachusetts - Compare and Save

The cheapest ticket to Massachusetts from Chicago found in the last 5 days was to Boston, at $148 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 5 days was $148.

The cheapest time of day to fly to Massachusetts is generally at night, when round-trip flights cost $231 on average. Morning departures are around 13% cheaper than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the evening, which is peak travel time and where the average cost of a ticket is $301.

No, with an average price for the route of $396, prices are generally cheapest when you fly direct.

The cheapest month for flights from Chicago to Massachusetts is January, when tickets cost $199 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $280 and $271 respectively.

If you are looking for a flight deal from Chicago to Massachusetts, look for departures on Saturdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Massachusetts, Friday is the cheapest day to fly and Sunday is the most expensive.

To get a below average price on the flight from Chicago to Massachusetts, you should book around 3 weeks before departure, which saves you about 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

There are 5 airlines that fly nonstop from Chicago to Massachusetts. They are: American Airlines, JetBlue, Southwest, Delta and United Airlines. The cheapest price of all airlines flying this route was found with JetBlue at $69 for a round-trip flight to Boston (BOS). On average, JetBlue offers the best prices for nonstop flights between Chicago and Massachusetts.

Chicago and Massachusetts are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (77 flights per week), American Airlines (73 flights per week), and Air New Zealand (72 flights per week).

The duration of a flight to Massachusetts depends on your arrival airport. The shortest routes to Massachusetts from Chicago are to Boston, which takes 2h 15m, Boston, which takes 2h 42m, and Boston, which takes 2h 50m.

There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

The earliest flight from Chicago to Massachusetts departs at 6:00 am, landing in Boston at 9:34 am.

If you prefer to fly at night, the latest flight from Chicago to Massachusetts jets off at 9:45 pm and lands in Boston at 1:15 am.