Cheap flights from Chicago Midway to Boston

Flights tailored to your budget

Selected dates may not give results due to COVID-19. We suggest you change the dates.
Multi-city Round trip One way
Round trip
One way
Multi-city
From
No results match your search criteria
To
No results match your search criteria
{{ weekDay }}
Dates
{{ panel.label }}
Looking for a one-way flight?

Flexible dates can save you money

Explore nearby dates to find lower fares

{{ fromDate | dateToLongNamedDate }}
?
Flexible dates
Depart {{ flexibleFromDateLabel }}
{{ option.label }}
?
Return {{ flexibleToDateLabel }}
{{ option.label }}
Passengers / Class
Number of passengers
Adults
{{ adults }}
Children
{{ children }}
Infants
{{ infants }}
Class
Economy
Available for Economy only
New Multi-city experience

Discover a new Multi-city search experience from Jetcost, designed to handle more complex itineraries. By continuing, you’ll be taken to a dedicated page powered by Kiwi.com.
How do we get the info you see here? Please note that we offer an online comparison service and that all information and prices regarding services and/or products available on our website are provided by our third-party partners. We do our best to show you up-to-date information, but please note that we are not responsible for the completeness or accuracy of the information published, so please check all conditions carefully on the website of the partner before making a booking. Please check our Terms and Conditions for more details. Read more

What’s the price of flying from Chicago Midway to Boston?

It depends. Prices for flights from Chicago to Boston fluctuate based on several factors.

Choose a date to explore the best fares now.

Checking flights with stopovers can sometimes lead to big savings, especially on longer routes. Also, airfare often depends on availability — it’s wise to track price changes regularly.

Exploring all airports near Chicago and Boston

Checking all the airports available in the area can give you more departure and arrival options for your trip.

  • Airports in Chicago: 3 different airports operate in Chicago - Midway, O'Hare, Rockford.
  • Airports in Boston: Boston - Logan is the only option available right now.

Looking at expected traffic to the airport can help avoid surprises on departure day. On busy routes, flying from a quieter airport might also save you money.

Flights from Chicago - Midway to Boston - Logan

Plan your journey from Chicago Midway to Boston with ease

Use Jetcost to tailor your search — direct or connecting flights, round-trip or one-way, filtered by airline, price, travel time, or agency.

Other popular destinations

Exploring options in United States? These cities are trending: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Flight availability can change quickly — refresh the results if you’ve been away from the page for a while.
Frequently Asked Questions

Frequently asked questions about flights from Chicago Midway to Boston.

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

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

How far is Chicago from Boston?

Chicago is about 1381 km from Boston.

What are the airports in Boston?

Boston has one airport: Boston - Logan.

What are the airports in Chicago?

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

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 Chicago to Boston?

This information is not available at the moment.

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

This information is not available at the moment.

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

This information is not available at the moment.

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

This information is not available at the moment.