How much is a ticket from Boston to Chicago Midway?

Depending on when you travel and how far in advance you book, fares between Boston and Chicago can differ a lot.

Choose a date to explore the best fares now.

If you’re flexible with timing, consider overnight flights — they often cost less and are less crowded. Exploring multiple date and time combinations can help you find the cheapest solution.

Flying from or to Boston and Chicago? Here are your airport options

Knowing your full list of nearby airports can make flight planning easier, especially when routes vary.

• Airports in Boston: Only Boston - Logan is available for departures.
• Airports in Chicago: Arrivals into Chicago are possible from 3 airports - Midway, O'Hare, Rockford.

For families or those traveling with assistance, smaller airports can be easier to navigate. Cities served by multiple airports often allow for more flexible travel planning.

Find flights from Boston to Chicago Midway that suit your schedule

Use Jetcost to sort and filter results based on your preferred flight time, number of stops, price range, or airline. View deals from Ryanair, British Airways, Easyjet, and booking sites like Expedia and eDreams.

Other popular destinations

Interested in United States? These cities are also in demand: Atlanta, Los Angeles, Miami, New York City, Orlando.

Connecting flights can be cheaper but often mean longer layovers. You can easily select either direct or connecting flights with a single click using the filters.