What’s the cost of a flight from Chicago Midway to Boston?

Prices vary based on date, airline, and availability. Compare several options if you're flying between Chicago and Boston.

Choose a date to explore the best fares now.

If possible, avoid holiday periods: ticket prices tend to rise quickly and availability drops, especially on busy routes. Morning and evening flights are often in high demand too — book early to get a good fare.

Airport options between Chicago and Boston

Even for routes around 858 mi, using different airports might affect flight cost and travel time.

• Airports in Chicago: You can fly from 3 airports in Chicago - Midway, O'Hare, Rockford.
• Airports in Boston: Boston - Logan is the only functioning airport.

Checking the average travel time to the airport can help you plan better. For some routes, changing your arrival or departure airport might also affect the price.

Explore flights from Chicago Midway to Boston your way

On Jetcost, you can filter by round-trip or one-way, time of day, airline, number of stops, and even by agency like eDreams or Expedia. Options include Delta, United, American, and more.

Other popular destinations

Also interested in United States? Check out: Las Vegas, Los Angeles, Miami, New York City, Orlando.

If you’re flexible with dates, try checking the days before and after to see if prices vary. Some routes are offered by multiple agencies — comparing fares can really pay off.