Cheap flights from Massachusetts to Chicago (CHI)

BOS — CHI
Aug 14 — Aug 211

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

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, January can be a great choice for travel to Chicago. Flights to Chicago from Massachusetts in January are about $218 on average during January, but can be found for as low as $97.

When is the cheapest time to fly from Massachusetts to Chicago (MA - CHI)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Massachusetts to Chicago as you normally would.

Cheap flights from Massachusetts to Chicago in August, September 2022

The best prices found for Massachusetts to CHI flights for August, September
Sep 18 - Sep 21
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 52m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 17m
$127

American Airlines

Pick Dates

Deal found 7.8.22

Sep 13 - Sep 21
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 56m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 17m
$128

JetBlue

Pick Dates

Deal found 8.8.22

Sep 3 - Sep 6
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

3h 03m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 26m
$133

JetBlue

Pick Dates

Deal found 6.8.22

Massachusetts to Chicago 2022 flight deals

Cheap flights to Chicago from Massachusetts found for this year
Oct 29 - Oct 29
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

3h 03m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 26m
$122

JetBlue

Pick Dates

Deal found 8.8.22

Sep 18 - Sep 21
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 52m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 17m
$127

American Airlines

Pick Dates

Deal found 7.8.22

Sep 13 - Sep 21
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 56m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 17m
$128

JetBlue

Pick Dates

Deal found 8.8.22

Cheap United Airlines flights from Massachusetts to Chicago

Sep 8 - Sep 11
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 51m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 21m
$158

United Airlines

Pick Dates

Deal found 8.8.22

Aug 31 - Sep 5
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 50m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 21m
$168

United Airlines

Pick Dates

Deal found 6.8.22

Aug 17 - Aug 18
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 50m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

1 stop

5h 02m
$172

United Airlines

Pick Dates

Deal found 7.8.22

Cheap Delta flights from Massachusetts to Chicago

Aug 25 - Aug 30
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 58m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 25m
$163

Delta

Pick Dates

Deal found 8.8.22

Aug 23 - Aug 30
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 58m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 25m
$173

Delta

Pick Dates

Deal found 8.8.22

Sep 21 - Sep 30
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 39m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 34m
$174

Delta

Pick Dates

Deal found 8.8.22

Non-stop flights to Chicago from Massachusetts

Save time with Massachusetts to Chicago direct flight deals
Oct 29 - Oct 29
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

3h 03m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 26m
$122

JetBlue

Pick Dates

Deal found 8.8.22

Sep 13 - Sep 27
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 41m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 34m
$127

Delta

Pick Dates

Deal found 9.8.22

Sep 13 - Sep 20
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

3h 02m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 24m
$128

JetBlue

Pick Dates

Deal found 9.8.22

Last minute flights from Massachusetts to Chicago

Late deals on return flights to Chicago from Massachusetts, departing today and this week
Aug 16 - Aug 16
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

1 stop

5h 05m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 17m
$141

American Airlines

Pick Dates

Deal found 8.8.22

Aug 16 - Aug 17
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

1 stop

8h 15m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

Nonstop

2h 18m
$145

American Airlines

Pick Dates

Deal found 8.8.22

Aug 16 - Aug 16
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

1 stop

5h 22m
ORD

Chicago O'Hare Intl

BOS

Boston Logan Intl

1 stop

5h 51m
$149

American Airlines

Pick Dates

Deal found 8.8.22

One-way flights to Chicago from Massachusetts

The cheapest one-way flights from Massachusetts to Chicago
Sep 7
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

3h 02m
$64

JetBlue

Pick Dates

Deal found 8.8.22

Sep 4
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 50m
$69

United Airlines

Pick Dates

Deal found 8.8.22

Oct 17
BOS

Boston Logan Intl

ORD

Chicago O'Hare Intl

1 stop

9h 00m
$71

Spirit Airlines

Pick Dates

Deal found 6.8.22

Related info for your journey

Useful info, stats and facts about Massachusetts to Chicago flights.

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 $200 on Cheapflights?

Yes, there are multiple flights from Massachusetts to Chicago for under $200. The cheapest flight booked recently is on JetBlue for just $122, but on average you can expect to pay $142.

Are there nonstop flights from Massachusetts to Chicago for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Massachusetts to Chicago under $200. A good price for a nonstop flight from Massachusetts to Chicago is less than $149.

Are there last-minute flights available from Massachusetts to Chicago for under $200?

There are currently 20+ open flights from Massachusetts to Chicago within the next 7 days for less than $200.

What days are nonstop flights available from Massachusetts to Chicago?

Nonstop flights are available for this route on the following days: Sunday, Wednesday, Friday, Saturday.

How many flights depart from Massachusetts to Chicago on average per day?

On average, you can expect to see 9 flights from Massachusetts to Chicago a day.
Morning (6am - Noon) - 56% of flight departures
Evening (6pm - Midnight) - 44% of flight departures

How long is the flight from Massachusetts to Chicago?

A quick flight from Massachusetts to Chicago can take about 2h 51m. JetBlue provides one of the quickest options available for as low as $122. The distance from Massachusetts to Chicago is about 869 mi. All flights are typically nonstop.

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

To fly one-way, consider booking your trip with JetBlue, which is currently one of the cheapest options available, starting at $64. United Airlines flights start at $69 while deals on Spirit Airlines start at $71 one-way.

What are the most popular routes from Massachusetts to Chicago?

While some choose either Boston Logan Intl - Chicago Midway or Worcester - Chicago O'Hare Intl, Boston Logan Intl - Chicago O'Hare Intl is the most popular route from Massachusetts to Chicago.

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

Consider Undisclosed Carrier, American Airlines or Alaska Airlines when booking your flight. These represent the most popular airlines when flying from Massachusetts to Chicago.

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: ANA (92%), Japan Airlines (83%), United Airlines (83%).

What are the cheapest flights from Massachusetts to Chicago?

Looking for the cheapest flight from Massachusetts to Chicago? While on average our users pay $462, our data indicates the cheapest price to be $73. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $122.

Departure points for flights from Massachusetts to Chicago

Select to see more specific information for flights to Chicago from all departure points in Massachusetts

Top 7 airlines flying from Massachusetts to Chicago

The chart below displays the airlines Cheapflights users traveling from Massachusetts to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$14Average$23FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
Spirit AirlinesCheapest$53Average$161FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
JetBlueCheapest$58Average$220FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search JetBlue flights
DeltaCheapest$69Average$269FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
United AirlinesCheapest$83Average$218FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
American AirlinesCheapest$97Average$299FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
Alaska AirlinesCheapest$249Average$343FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights

Hourly flight availability from Massachusetts to Chicago

See what time of day planes typically take off from Massachusetts to Chicago
17%of flight departuresEarly morningMidnight to 6 am
32%of flight departuresMorning6 am to noon
42%of flight departuresAfternoonNoon to 6 pm
9%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM