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$67+ Cheap flights from Massachusetts to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
abr. 29 — may. 61
mié. 4/29
mié. 5/6
1 adult, Economy
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Cheap flight deals from Massachusetts to Chicago

Cheapest flights from Massachusetts to Chicago
Explore the most affordable flight options available from Massachusetts to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on marzo 30, 2026.

This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/147:20 am
BOS
-
MDW
Nonstop2h 45m
Southwest
mar. 4/2112:45 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 3/25$135
This American Airlines deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/133:16 pm
BOS
-
ORD
Nonstop3h 14m
American Airlines
mar. 5/196:00 am
ORD
-
BOS
Nonstop2h 27m
American Airlines
Deal found 3/25$135
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/1410:45 am
BOS
-
MDW
Nonstop2h 40m
Southwest
mié. 4/153:15 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 3/26$136
This American Airlines deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/153:16 pm
BOS
-
ORD
Nonstop3h 14m
American Airlines
mié. 4/226:00 am
ORD
-
BOS
Nonstop2h 27m
American Airlines
Deal found 3/26$136
This SmartFares deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/307:02 am
BOS
-
ORD
Nonstop2h 57m
JetBlue
dom. 5/36:00 am
ORD
-
BOS
Nonstop2h 15m
JetBlue
Deal found 3/29$137
This Priceline deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/287:35 pm
BOS
-
ORD
Nonstop3h 04m
Multiple Airlines
lun. 5/44:28 pm
ORD
-
BOS
1 stop8h 03m
Multiple Airlines
Deal found 3/26$138
This Expedia deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/211:16 am
BOS
-
MDW
1 stop21h 25m
Frontier
lun. 5/42:15 pm
MDW
-
BOS
1 stop10h 16m
Frontier
Deal found 3/25$140
This Frontier deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/2712:31 pm
BOS
-
ORD
1 stop11h 30m
Frontier
mar. 5/51:59 pm
ORD
-
BOS
1 stop10h 25m
Frontier
Deal found 3/27$140
This flygcity.se deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/307:02 am
BOS
-
ORD
Nonstop2h 57m
JetBlue
lun. 5/46:00 am
ORD
-
BOS
Nonstop2h 15m
JetBlue
Deal found 3/25$141
This Priceline deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/2712:42 pm
BOS
-
ORD
1 stop10h 57m
Multiple Airlines
mié. 4/299:41 am
ORD
-
BOS
Nonstop2h 28m
Multiple Airlines
Deal found 3/25$143
This Super.com deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/66:47 pm
BOS
-
ORD
Nonstop3h 06m
JetBlue
jue. 5/77:20 am
ORD
-
BOS
Nonstop2h 26m
JetBlue
Deal found 3/26$144
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/226:00 pm
BOS
-
MDW
1 stop5h 15m
Southwest
mié. 4/293:15 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 3/25$145

Find flight deals from Massachusetts to Chicago

Keep the following information in mind while searching for Massachusetts to Chicago flight deals. Data was last updated marzo 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$135
(Southwest)

One-way from

$67
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$267

Good round-trip deal

$239 or less

Good one-way deal

$129 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
Search Deals
From Massachusetts to Chicago (CHI)
Search Deals
One-way flight from Massachusetts to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Massachusetts to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Massachusetts to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated marzo 30, 2026.
Use the filters below to find and compare flights from Massachusetts to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mar. 5/26

6:00 am-7:58 am

Nonstop2h 58m

Chicago O'Hare Intl

dom. 5/31

6:15 am-9:39 am

Nonstop2h 24m

$146

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 4/30

7:10 am-9:15 am

Nonstop3h 05m

Chicago O'Hare Intl

lun. 5/4

6:50 am-10:11 am

Nonstop2h 21m

$156

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 7/30

6:45 pm-8:45 pm

Nonstop3h 00m

Chicago O'Hare Intl

mar. 8/4

9:35 pm-1:08 am

Nonstop2h 33m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

dom. 5/10

7:35 am-9:27 am

Nonstop2h 52m

Chicago O'Hare Intl

sáb. 5/16

7:00 am-10:35 am

Nonstop2h 35m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jue. 6/4

4:45 pm-6:35 pm

Nonstop2h 50m

Chicago Midway

mar. 6/9

2:35 pm-10:40 pm

1 stop7h 05m

$167

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

sáb. 4/25

3:15 pm-8:05 pm

1 stop5h 50m

Chicago Midway

mié. 4/29

7:45 am-11:00 am

Nonstop2h 15m

$167

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

vie. 5/8

6:39 pm-8:40 pm

Nonstop3h 01m

Chicago O'Hare Intl

dom. 5/10

7:30 am-11:01 am

Nonstop2h 31m

$167

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

mié. 5/13

8:10 am-3:45 pm

2 stops8h 35m

Chicago Midway

lun. 5/18

7:40 am-10:55 am

Nonstop2h 15m

$172

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 8/20

7:30 am-9:28 am

Nonstop2h 58m

Chicago O'Hare Intl

dom. 8/30

7:00 am-10:28 am

Nonstop2h 28m

$177

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

vie. 5/8

7:26 pm-11:37 pm

1 stop5h 11m

Chicago O'Hare Intl

lun. 5/11

6:00 am-9:25 am

Nonstop2h 25m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Massachusetts to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Massachusetts with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Massachusetts to Chicago

What is the cheapest month to book a flight from Massachusetts to Chicago?

Currently, September is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $91). Flying from Massachusetts to Chicago in January is currently the most expensive (average of $123). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MA to CHI?

Find hourly flight availability from Massachusetts to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated marzo 30, 2026.

When flying from Massachusetts to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 47% versus a flight in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Chicago. Price data was last updated on March 28, 2026.

Travelers seeking maximum savings on their Massachusetts to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Massachusetts to Chicago

Explore weekly flight availability from Massachusetts to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated marzo 30, 2026.

The most flights from USMA to CHI are scheduled on a Sunday (67 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).

How much does it cost to fly round-trip from Massachusetts to Chicago?

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Massachusetts to Chicago?

    A quick flight from Massachusetts to Chicago can take about 2h 50m. United Airlines provides one of the quickest options available for as low as $167. The distance from Massachusetts to Chicago is about 857 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 Southwest, which is currently one of the cheapest options available, starting at $58. Delta flights start at $58 while deals on JetBlue start at $58 one-way.

  • What are the most popular routes from Massachusetts to Chicago?

    While some choose either Boston Logan Intl - Chicago Midway or Hartford Bradley Intl - Chicago O'Hare Intl, Boston Logan Intl - Chicago O'Hare Intl is the most popular route 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: Icelandair (100%), WestJet (87%), Air France (80%).

  • What are the cheapest flights from Massachusetts to Chicago?

    Looking for the cheapest flight from Massachusetts to Chicago? While on average our users pay $558, our data indicates the cheapest price to be $75. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $152.

  • Can I find deals for flights from Massachusetts to Chicago that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Chicago.

  • Can I find deals for business class flights from Massachusetts to Chicago?

    Yes. Cheapflights offers flight deals from Massachusetts to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Massachusetts to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $91). Flying from Massachusetts to Chicago in January is currently the most expensive (average of $123). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Massachusetts to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Massachusetts to Chicago

Discover the top 6 airlines that operate flights from Massachusetts to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated marzo 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$32Average$162FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$67Average$177FlexibilityNo cancel feeOn-time62%
DeltaCheapest$84Average$320FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$117Average$219FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$117Average$260FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$128Average$258FlexibilityNo cancel feeOn-time71%

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