Cheap flights from Massachusetts (MA) to Chicago (CHI)

Flight FAQs

From Massachusetts to Chicago

Are flight prices decreasing from Massachusetts to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Massachusetts and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Massachusetts to Chicago to control the spread of COVID-19?

Delta is one of the many airlines that have implemented additional safety measures to control the spread of COVID-19. New policies for travelers booking flights from Massachusetts to Chicago include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

Which airlines flying from Massachusetts to Chicago have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Massachusetts to Chicago that may be offering flexible cancellation policies are United Airlines, American Airlines, and JetBlue. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Massachusetts to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Massachusetts to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $38, but on average you can expect to pay $47.

Are there nonstop flights from Massachusetts to Chicago for under $100 on Cheapflights?

Cheapflights has at least 20 direct flights from Massachusetts to Chicago under $100. A good price for a nonstop flight from Massachusetts to Chicago is less than $48.

Are there last-minute flights available from Massachusetts to Chicago for under $100?

There are currently 20+ open flights from Massachusetts to Chicago within the next 7 days for less than $100.

What days are nonstop flights available from Massachusetts to Chicago?

You can find nonstop flights on the following days: Monday, Tuesday, Wednesday, Thursday, Friday, Saturday.

What are the most popular airlines that fly from Massachusetts to Chicago?

Consider Major Airline, American Airlines or JetBlue when booking your flight. These represent the most popular airlines when flying from Massachusetts to Chicago.

What are the most popular routes from Massachusetts to Chicago?

Most travelers choose Boston Logan Intl - Chicago O'Hare Intl, Boston Logan Intl - Chicago Midway or Boston Logan Intl - Chicago Greater Rockford when deciding on the best route from Massachusetts to Chicago.

What are the cheapest Flights from Massachusetts to Chicago?

On average you can expect to pay $345 for a flight from Massachusetts to Chicago. The cheapest flight overall is $54 while the most popular route, (Boston Logan Intl - Chicago O'Hare Intl) is currently priced at $38.

What are the most reliable airlines from Massachusetts to Chicago?

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Massachusetts to Chicago on time: Japan Airlines(97%), ANA(89%), United Airlines(86%.)

How long is the flight from Massachusetts to Chicago?

Departing from Massachusetts to Chicago will take you 2h 50m. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What is the cheapest airline to fly from Massachusetts to Chicago round-trip?

Currently priced at $38, Spirit Airlines will fly you from Massachusetts to Chicago and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip.

What are the cheapest airlines to fly from Massachusetts to Chicago one-way?

One-way options have recently been found by users for as low as $18 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $43 and Frontier from $52 one-way.