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$67+ Cheap flights from Boston (BOS) 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Boston to Illinois

Keep the following information in mind while searching for Boston to Illinois flight deals. Data was last updated September 11, 2025.

Round-trip from

$125
(Southwest)

One-way from

$67
(Southwest)

Popular in

March

Cheapest in

September

Average price

$184

Good round-trip deal

$192 or less

Good one-way deal

$114 or less
From Boston Logan Intl to Illinois
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One-way flight from Boston Logan Intl to Illinois
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Highest demand for flights based on searches. 7% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Boston Logan Intl to Illinois.
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Price to beat on a one-way flight from Boston Logan Intl to Illinois.
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Find flight deals from Boston to Illinois

Cheapest flights from Boston to Illinois
Explore the most affordable flight options available from Boston to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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 10/256:30 amBOS - MDW
2 stops10h 55mSouthwest
Mon 10/2711:25 amMDW - BOS
1 stop6h 50mSouthwest
Deal found 9/11$125
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Wed 10/89:53 amBOS - ORD
Nonstop2h 50mUnited Airlines
Tue 10/149:00 amORD - BOS
Nonstop2h 35mUnited Airlines
Deal found 9/10$125
This Southwest deal was found by Cheapflights users on 9/11. 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 10/315:00 amBOS - MDW
Nonstop2h 40mSouthwest
Mon 11/36:40 amMDW - BOS
1 stop8h 55mSouthwest
Deal found 9/11$126
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:16 amBOS - ORD
1 stop13h 22mSpirit Airlines
Tue 10/216:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Deal found 9/11$126
This Delta deal was found by Cheapflights users on 9/10. 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 10/259:00 amBOS - ORD
1 stop4h 40mDelta
Mon 10/277:10 pmORD - BOS
Nonstop2h 35mDelta
Deal found 9/10$127
This Southwest deal was found by Cheapflights users on 9/10. 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 11/45:35 pmBOS - MDW
1 stop4h 30mSouthwest
Wed 11/58:25 amMDW - BOS
2 stops7h 10mSouthwest
Deal found 9/10$129
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/76:57 amBOS - ORD
Nonstop2h 58mAmerican Airlines
Sun 10/127:00 amORD - BOS
Nonstop2h 21mAmerican Airlines
Deal found 9/10$129
This Southwest deal was found by Cheapflights users on 9/9. 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 10/256:30 amBOS - MDW
2 stops10h 55mSouthwest
Mon 11/36:40 amMDW - BOS
1 stop8h 55mSouthwest
Deal found 9/9$130
This Southwest deal was found by Cheapflights users on 9/11. 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.
Wed 10/296:45 amBOS - ORD
1 stop8h 15mSouthwest
Wed 11/121:45 pmORD - BOS
1 stop7h 30mSouthwest
Deal found 9/11$130
This Southwest deal was found by Cheapflights users on 9/11. 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 10/305:15 amBOS - MDW
Nonstop2h 40mSouthwest
Sun 11/25:45 amMDW - BOS
1 stop10h 25mSouthwest
Deal found 9/11$131
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Fri 10/34:25 pmBOS - ORD
Nonstop2h 55mUnited Airlines
Sun 10/1211:05 amORD - BOS
Nonstop2h 35mUnited Airlines
Deal found 9/10$131
This Southwest deal was found by Cheapflights users on 9/11. 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 10/249:35 pmBOS - MDW
Nonstop2h 40mSouthwest
Sun 10/266:05 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/11$132

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston 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 September 11, 2025.
Use the filters below to find and compare flights from Boston to Illinois that are best for you.

Fly from

Boston

Fly to

Illinois

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/31

5:00 am-6:40 am

Nonstop2h 40m

Chicago Midway

Mon 11/3

6:40 am-4:35 pm

1 stop8h 55m

$126

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 11/13

5:29 am-8:52 am

1 stop4h 23m

Chicago Midway

Mon 11/17

6:48 pm-11:55 pm

1 stop4h 07m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 11/25

5:35 pm-7:50 pm

Nonstop3h 15m

Chicago O'Hare Intl

Sat 11/29

8:25 pm-11:57 pm

Nonstop2h 32m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 11/13

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sun 11/16

6:15 am-9:30 am

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 11/10

1:45 pm-3:30 pm

Nonstop2h 45m

Chicago Midway

Fri 11/14

7:15 pm-10:30 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 10/15

5:34 am-8:40 am

1 stop4h 06m

Chicago Midway

Tue 10/21

1:08 pm-8:01 pm

1 stop5h 53m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/25

4:40 pm-6:55 pm

Nonstop3h 15m

Chicago O'Hare Intl

Sat 9/27

9:51 am-1:20 pm

Nonstop2h 29m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 10/15

5:15 am-6:55 am

Nonstop2h 40m

Chicago Midway

Sat 10/18

12:45 pm-4:00 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 11/1

5:45 am-1:08 pm

1 stop8h 23m

Chicago Midway

Sat 11/8

1:06 pm-5:52 pm

1 stop3h 46m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 11/1

11:45 am-1:40 pm

Nonstop2h 55m

Chicago O'Hare Intl

Sat 11/8

10:25 am-1:55 pm

Nonstop2h 30m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 60 results
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Best time to book a flight from Boston to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Boston 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 Boston to Illinois

What is the cheapest month to book a flight from Boston to Illinois?

Currently, August is the cheapest month in which you can book a flight from Boston to Illinois (average of $245). Flying from Boston to Illinois 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 BOS to IL?

Find hourly flight availability from Boston 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 September 11, 2025.

When flying from Boston to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Boston to Illinois

Explore weekly flight availability from Boston 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 September 11, 2025.

The most flights from BOS to USIL are scheduled on a Thursday (77 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 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 September 11, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Boston to Illinois to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,913 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

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

  • What airport do you fly from for flights from Boston to Illinois?

    If you book a flight to Illinois from Boston, you will be flying from Logan Intl, which is the city’s only airport. Boston Logan Intl (BOS) is located 2.6 mi from the center of Boston.

  • How long is the flight from Boston to Illinois?

    Departing from Boston to Illinois will take you 2h 40m. There are 857 mi between Boston and Illinois. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Boston to Illinois one-way?

    The cheapest airlines for a one-way flight from Boston to Illinois are Southwest ($67), Delta ($69), and American Airlines ($126).

  • What are the most popular routes from Boston to Illinois?

    The most popular flight routes from Boston to Illinois are Boston Logan Intl - Chicago O'Hare Intl, Boston Logan Intl - Chicago Midway and Boston Logan Intl - Lambert-St Louis.

  • What are the most reliable airlines from Boston to Illinois?

    No one likes to see their flight delayed. When booking a flight from Boston to Illinois consider choosing Icelandair (89%), TAP AIR PORTUGAL (89%) or Avianca (85%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Boston to Illinois?

    While on average a flight from Boston to Illinois is generally $761, our data shows the cheapest flight currently is $59. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay $117 for that flight.

  • Can I find deals for flights from Boston to Illinois that include hotel bookings?

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

  • How can I find direct flights from Boston to Illinois?

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

  • Can I find deals for business class flights from Boston to Illinois?

    Yes. Cheapflights offers flight deals from Boston to Illinois 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 Boston to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Boston to Illinois (average of $245). Flying from Boston to Illinois 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.

See more FAQs

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Alternative routes for Boston to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Boston to Illinois

Discover the top 7 airlines that operate flights from Boston 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$203FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$81Average$199FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$97Average$456FlexibilityNo cancel feeOn-time69%
DeltaCheapest$98Average$356FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$107FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$121Average$233FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$137Average$433FlexibilityNo cancel feeOn-time71%

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