$69+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Jul 8 — Jul 151
1 adult, Economy
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Find cheap flights from Massachusetts to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Massachusetts to Chicago
Keep the following information in mind while searching for Massachusetts to Chicago flight deals. Data was last updated July 3, 2025.
Round-trip from | $137 (Southwest) |
|---|---|
One-way from | $69 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $223 |
Good round-trip deal | $137 or less |
Good one-way deal | $123 or less |
Find flight deals from Massachusetts to Chicago
Cheapest flights from Massachusetts to ChicagoExplore 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 July 3, 2025.
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 July 3, 2025.
This Southwest deal was found by Cheapflights users on 7/2. 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.
Thu 7/105:15 amBOS - MDW
Nonstop2h 35mSouthwest
Tue 7/155:05 amMDW - BOS
Nonstop2h 10mSouthwest
Deal found 7/2![Southwest logo]()
$137
This Delta deal was found by Cheapflights users on 7/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/237:20 amBOS - ORD
Nonstop2h 58mDelta
Mon 7/287:00 amORD - BOS
Nonstop2h 31mDelta
Deal found 7/3![Delta logo]()
$137
This FlightHub deal was found by Cheapflights users on 7/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/306:15 amBOS - ORD
1 stop10h 16mSpirit Airlines
Wed 8/65:05 amORD - BOS
1 stop13h 29mSpirit Airlines
Deal found 7/2![Spirit Airlines logo]()
$138
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Tue 7/152:55 pmBOS - ORD
Nonstop3h 07mAmerican Airlines
Thu 7/178:30 pmORD - BOS
Nonstop2h 44mAmerican Airlines
Deal found 7/2![American Airlines logo]()
$139
This United Airlines deal was found by Cheapflights users on 7/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/157:04 pmBOS - ORD
1 stop5h 37mUnited Airlines
Tue 7/223:48 pmORD - BOS
Nonstop2h 30mUnited Airlines
Deal found 7/1![United Airlines logo]()
$143
This Priceline deal was found by Cheapflights users on 7/3. 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.
Thu 7/176:00 amBOS - ORD
1 stop9h 04mFrontier
Sat 7/1912:20 pmORD - BOS
1 stop11h 19mFrontier
Deal found 7/3![Frontier logo]()
$144
This Priceline deal was found by Cheapflights users on 7/3. 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.
Sun 8/249:20 amBOS - ORD
1 stop10h 21mMultiple Airlines
Wed 8/2711:36 amORD - BOS
1 stop11h 13mMultiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$145
This Priceline deal was found by Cheapflights users on 7/2. 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.
Sat 8/169:40 amBOS - MDW
1 stop11h 42mFrontier
Sun 8/173:58 pmMDW - BOS
1 stop7h 40mFrontier
Deal found 7/2![Frontier logo]()
$149
This Southwest deal was found by Cheapflights users on 7/3. 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.
Tue 7/155:45 amBOS - ORD
1 stop7h 05mSouthwest
Sat 7/191:30 pmORD - BOS
1 stop6h 35mSouthwest
Deal found 7/3![Southwest logo]()
$157
This JetBlue deal was found by Cheapflights users on 7/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/267:00 amBOS - ORD
Nonstop2h 55mJetBlue
Tue 7/298:40 amORD - BOS
Nonstop2h 24mJetBlue
Deal found 7/3![JetBlue logo]()
$182
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Mon 7/213:29 pmORH - ORD
2 stops9h 28mAmerican Airlines
Wed 7/238:41 pmORD - ORH
1 stop17h 23mAmerican Airlines
Deal found 7/1![American Airlines logo]()
$198
This Mytrip deal was found by Cheapflights users on 7/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:10 amBOS - RFD
2 stops9h 15mMultiple Airlines
Mon 9/2910:37 amRFD - BOS
2 stops23h 36mMultiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$209
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 July 3, 2025.
Use the filters below to find and compare flights from Massachusetts to Chicago that are best for you.
Fly from
Massachusetts
Fly to
Chicago
Route
Depart
Return
Price
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 7/15
7:20 am-9:00 am
Nonstop2h 40m
Chicago Midway
Thu 7/17
8:05 am-11:20 am
Nonstop2h 15m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 7/23
7:20 am-9:18 am
Nonstop2h 58m
Chicago O'Hare Intl
Mon 7/28
7:00 am-10:31 am
Nonstop2h 31m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 7/30
8:39 pm-8:55 am
1 stop13h 16m
Chicago O'Hare Intl
Tue 8/5
5:05 am-7:34 pm
1 stop13h 29m
$138
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/15
2:55 pm-5:02 pm
Nonstop3h 07m
Chicago O'Hare Intl
Thu 7/17
8:30 pm-12:14 am
Nonstop2h 44m
$139
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/15
7:04 pm-11:41 pm
1 stop5h 37m
Chicago O'Hare Intl
Tue 7/22
3:48 pm-7:18 pm
Nonstop2h 30m
$143
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 7/17
6:00 am-2:04 pm
1 stop9h 04m
Chicago O'Hare Intl
Sat 7/19
12:20 pm-12:39 am
1 stop11h 19m
$144
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 8/24
9:20 am-6:41 pm
1 stop10h 21m
Chicago O'Hare Intl
Wed 8/27
11:36 am-11:49 pm
1 stop11h 13m
$145
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 8/16
9:40 am-8:22 pm
1 stop11h 42m
Chicago Midway
Sun 8/17
3:58 pm-12:38 am
1 stop7h 40m
$149
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/15
5:45 am-11:50 am
1 stop7h 05m
Chicago O'Hare Intl
Sat 7/19
1:30 pm-9:05 pm
1 stop6h 35m
$157
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 7/26
7:00 am-8:55 am
Nonstop2h 55m
Chicago O'Hare Intl
Tue 7/29
8:40 am-12:04 pm
Nonstop2h 24m
$182
Showing 1-10 of 60 results
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, August is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $245). Flying from Massachusetts to Chicago in March is currently the most expensive (average of $321). 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 July 3, 2025.
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.
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 July 3, 2025.
The most flights from USMA to CHI are scheduled on a Thursday (80 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 3, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Massachusetts to Chicago have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.2
Entertainment
7.6
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
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.
Traveling to a place near Massachusetts?
Book flights to Massachusetts if you plan to visit one of these locationsMerrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton
Browse thousands of different options on Cheapflights for your next trip
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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.
Top 7 airlines flying from Massachusetts to Chicago
Discover the top 7 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 July 3, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$41 | Average$111 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$78 | Average$203 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$94 | Average$312 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$97 | Average$233 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$100 | Average$117 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$124 | Average$303 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$136 | Average$254 | FlexibilityNo cancel fee | On-time71% |