$67+ Cheap flights from Massachusetts to Illinois
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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Feb 19 — Feb 261
1 adult, Economy
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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 Illinois
Cheapest flights from Massachusetts to IllinoisExplore the most affordable flight options available from Massachusetts to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 20, 2026.
Explore the most affordable flight options available from Massachusetts to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 20, 2026.
This Southwest deal was found by Cheapflights users on 1/20. 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.
Sat 2/75:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sun 2/81:50 pm
MDW
- BOS
1 stop6h 35m
Southwest
Deal found 1/20![Southwest logo]()
$132
This Flysmarter deal was found by Cheapflights users on 1/18. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/73:35 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Mon 2/99:40 am
ORD
- BOS
1 stop4h 54m
JetBlue
Deal found 1/18![JetBlue logo]()
$132
This Expedia deal was found by Cheapflights users on 1/18. 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.
Tue 2/33:35 pm
BOS
- ORD
Nonstop3h 08m
Multiple Airlines
Tue 2/106:07 pm
ORD
- BOS
1 stop6h 06m
Multiple Airlines
Deal found 1/18![Multiple Airlines logo]()
$133
This American Airlines deal was found by Cheapflights users on 1/20. 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.
Sat 2/285:54 pm
BOS
- ORD
Nonstop3h 06m
American Airlines
Sun 3/16:26 am
ORD
- BOS
Nonstop2h 28m
American Airlines
Deal found 1/20![American Airlines logo]()
$134
This Southwest deal was found by Cheapflights users on 1/19. 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.
Fri 2/65:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Mon 2/96:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 1/19![Southwest logo]()
$135
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Thu 1/296:00 am
BOS
- ORD
Nonstop3h 04m
United Airlines
Thu 1/294:15 pm
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 1/20![United Airlines logo]()
$135
This American Airlines deal was found by Cheapflights users on 1/18. 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.
Sat 2/76:10 am
BOS
- ORD
Nonstop3h 10m
American Airlines
Mon 2/94:30 pm
ORD
- BOS
Nonstop2h 14m
American Airlines
Deal found 1/18![American Airlines logo]()
$136
This Southwest deal was found by Cheapflights users on 1/17. 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.
Sun 1/255:20 am
BOS
- MDW
Nonstop2h 50m
Southwest
Tue 1/272:00 pm
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 1/17![Southwest logo]()
$137
This Delta deal was found by Cheapflights users on 1/20. 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.
Sat 2/75:15 pm
BOS
- ORD
Nonstop3h 11m
Delta
Sun 2/87:05 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 1/20![Delta logo]()
$137
This Southwest deal was found by Cheapflights users on 1/19. 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.
Sat 2/712:55 pm
BOS
- MDW
2 stops6h 45m
Southwest
Mon 2/96:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 1/19![Southwest logo]()
$138
This Bravofly deal was found by Cheapflights users on 1/18. 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 Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Wed 3/116:04 am
ORD
- BOS
1 stop7h 16m
JetBlue
Deal found 1/18![JetBlue logo]()
$138
This Rumbo deal was found by Cheapflights users on 1/19. 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 Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/710:15 am
BOS
- ORD
1 stop10h 16m
JetBlue
Sun 2/87:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Deal found 1/19![JetBlue logo]()
$140
Find flight deals from Massachusetts to Illinois
Keep the following information in mind while searching for Massachusetts to Illinois flight deals. Data was last updated January 20, 2026.
Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $132 (Southwest) |
One-way from | $67 (Kiwi.com) |
Popular in | April |
Cheapest in | September |
Average price | $205 |
Good round-trip deal | $228 or less |
Good one-way deal | $129 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Illinois 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 January 20, 2026.
Use the filters below to find and compare flights from Massachusetts to Illinois that are best for you.
Fly from
Massachusetts
Fly to
Illinois
Route
Depart
Return
Price
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 3/11
7:15 am-9:25 am
Nonstop3h 10m
Chicago O'Hare Intl
Tue 3/17
7:00 am-10:25 am
Nonstop2h 25m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 3/25
7:15 am-9:25 am
Nonstop3h 10m
Chicago O'Hare Intl
Sun 4/5
6:15 am-9:40 am
Nonstop2h 25m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 4/14
7:35 pm-9:29 pm
Nonstop2h 54m
Chicago O'Hare Intl
Mon 4/20
7:00 am-10:30 am
Nonstop2h 30m
$135
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 1/23
5:30 am-7:20 am
Nonstop2h 50m
Chicago Midway
Fri 1/30
5:35 pm-8:50 pm
Nonstop2h 15m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 2/2
3:35 pm-5:43 pm
Nonstop3h 08m
Chicago O'Hare Intl
Fri 2/6
7:40 am-11:05 am
Nonstop2h 25m
$137
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sun 3/1
5:00 am-6:55 am
Nonstop2h 55m
Chicago Midway
Tue 3/3
2:00 pm-5:10 pm
Nonstop2h 10m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 2/7
5:15 pm-7:26 pm
Nonstop3h 11m
Chicago O'Hare Intl
Sun 2/8
7:05 am-10:40 am
Nonstop2h 35m
$137
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 2/7
12:55 pm-6:40 pm
2 stops6h 45m
Chicago Midway
Mon 2/9
6:35 pm-9:50 pm
Nonstop2h 15m
$138
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 3/24
12:07 pm-5:01 pm
1 stop5h 54m
Chicago O'Hare Intl
Tue 3/31
11:17 am-2:48 pm
Nonstop2h 31m
$141
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 4/13
6:55 pm-8:45 pm
Nonstop2h 50m
Chicago Midway
Thu 4/16
7:00 pm-10:20 pm
Nonstop2h 20m
$142
Showing 1-10 of 60 results
Best time to book a flight from Massachusetts to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois 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 Illinois
What is the cheapest month to book a flight from Massachusetts to Illinois?
Currently, April is the cheapest month in which you can book a flight from Massachusetts to Illinois (average of $89). Flying from Massachusetts to Illinois 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 IL?
Find hourly flight availability from Massachusetts to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 20, 2026.
A simple way to save on the total cost of your ticket is to fly from Massachusetts to Illinois in the evening. If you’re flexible enough to do this you can expect to save up to 59% on your trip compared to booking a flight in the morning.
What is the cheapest day to fly from Massachusetts to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Illinois. Price data was last updated on January 17, 2026.
Travelers seeking maximum savings on their Massachusetts to Illinois flight should consider departing on Wednesday at noon 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 Illinois
Explore weekly flight availability from Massachusetts to Illinois. 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 January 20, 2026.
The most flights from USMA to USIL are scheduled on a Monday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated January 20, 2026.
See what other customers who have flown with Southwest, Delta, and United Airlines from Massachusetts to Illinois have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Massachusetts to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Massachusetts to Illinois
Discover the top 6 airlines that operate flights from Massachusetts to Illinois. 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 January 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$45 | Average$145 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$67 | Average$178 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$82 | Average$282 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$217 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$117 | Average$392 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$128 | Average$424 | FlexibilityNo cancel fee | On-time71% |