Cheap flights from Boston to Chicago Midway

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How much is a flight from Boston to Chicago Midway?

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

Pick a travel date to see today’s available fares.

Fares change often — checking several times throughout the week can make a big difference. Booking in advance often means access to lower prices for the Boston - Chicago Midway route.

Which airports serve Boston and Chicago?

When planning a trip of about 1381 km, it's a good idea to check flights from surrounding airports too.

  • Airports in Boston: Boston - Logan is the only operational airport in the area.
  • Airports in Chicago: Chicago offers flights from 3 airports - Midway, O'Hare, Rockford.

The closest airport isn’t always the cheapest — it’s worth checking the alternatives too. In some cities, smaller airports offer lower fares than the main ones.

Flights from Boston - Logan to Chicago - Midway

Compare flights from Boston to Chicago Midway with advanced filters

Find your ideal flight using Jetcost. Select whether you want nonstop or connecting flights, round-trip or one-way, and filter by airline, price, or booking site.

Other popular destinations

Looking for alternatives in United States? Travelers also liked: Las Vegas, Los Angeles, Miami, New York City, Orlando.

If you have a preferred time to leave or arrive, filters can help you show only the matching flights. You can also filter by your favorite airline and see only those deals.
Frequently Asked Questions

Frequently asked questions about flights from Boston to Chicago Midway.

How much does an airline ticket from Boston to Chicago Midway cost?

Flight prices can vary a lot depending on the period and destination. At the moment, this information is not available for flights from Boston to Chicago Midway.

How far is Boston from Chicago?

Boston is about 1381 km from Chicago.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the airports in Boston?

Boston has one airport: Boston - Logan.

What are the most popular cities in United States?

The most popular cities in United States according to our users' searches are: Las Vegas, Los Angeles, Miami, New York City, Orlando.

When should I book a flight from Boston to Chicago?

The best time to book a flight from Boston to Chicago is 2 months in advance, while the worst time is 9 weeks in advance.

What is the cheapest month to fly from Boston to Chicago?

This information is not available at the moment.

What is the most expensive month to fly from Boston to Chicago?

This information is not available at the moment.

What is the best day of the week to fly from Boston to Chicago?

This information is not available at the moment.