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$64+ 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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Jul 19 — Jul 261
Sat 7/19
Sat 7/26
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 July 14, 2025.

Round-trip from

$137
(Southwest)

One-way from

$64
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$223

Good round-trip deal

$161 or less

Good one-way deal

$132 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. 9% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 14, 2025.

This Southwest deal was found by Cheapflights users on 7/14. 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 10/39:35 pmBOS - MDW
Nonstop2h 40mSouthwest
Sun 10/56:05 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 7/14$137
This JetBlue deal was found by Cheapflights users on 7/13. 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.
Wed 8/206:00 amBOS - ORD
Nonstop2h 55mJetBlue
Wed 8/278:40 amORD - BOS
Nonstop2h 24mJetBlue
Deal found 7/13$137
This FlightHub deal was found by Cheapflights users on 7/13. 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 8/203:37 pmBOS - ORD
1 stop7h 45mSpirit Airlines
Wed 8/2711:36 amORD - BOS
1 stop11h 13mSpirit Airlines
Deal found 7/13$138
This Southwest deal was found by Cheapflights users on 7/14. 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 8/305:20 amBOS - ORD
1 stop7h 30mSouthwest
Wed 9/36:00 amORD - BOS
2 stops10h 05mSouthwest
Deal found 7/14$142
This Delta deal was found by Cheapflights users on 7/13. 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.
Thu 9/254:05 pmBOS - ORD
Nonstop2h 54mDelta
Sat 9/277:25 amORD - BOS
Nonstop2h 30mDelta
Deal found 7/13$147
This American Airlines deal was found by Cheapflights users on 7/12. 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.
Fri 8/155:28 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Tue 8/196:15 amORD - BOS
Nonstop2h 28mAmerican Airlines
Deal found 7/12$165
This United Airlines deal was found by Cheapflights users on 7/12. 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 8/205:30 amBOS - ORD
1 stop5h 06mUnited Airlines
Wed 8/203:48 pmORD - BOS
Nonstop2h 31mUnited Airlines
Deal found 7/12$177
This Mytrip deal was found by Cheapflights users on 7/14. 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 9/58:59 amBOS - MDW
1 stop8h 44mAllegiant Air
Mon 9/87:50 pmMDW - BOS
1 stop12h 53mAllegiant Air
Deal found 7/14$201
This Mytrip deal was found by Cheapflights users on 7/13. 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.
Thu 9/116:49 pmBOS - MDW
2 stops22h 54mMultiple Airlines
Mon 9/157:50 pmMDW - BOS
1 stop12h 53mMultiple Airlines
Deal found 7/13$239
This Mytrip deal was found by Cheapflights users on 7/13. 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.
Mon 7/289:32 amBOS - PIA
1 stop6h 26mMultiple Airlines
Fri 8/19:06 pmPIA - BOS
2 stops25h 42mMultiple Airlines
Deal found 7/13$242
This Mytrip deal was found by Cheapflights users on 7/13. 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 10/2411:34 amBOS - RFD
1 stop8h 19mMultiple Airlines
Sun 10/264:45 pmRFD - BOS
1 stop16h 51mMultiple Airlines
Deal found 7/13$244
This FlightHub deal was found by Cheapflights users on 7/14. 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.
Sun 8/3110:36 amBOS - MDW
1 stop5h 05mFrontier
Thu 9/45:04 pmMDW - BOS
1 stop15h 54mFrontier
Deal found 7/14$244

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 July 14, 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 10/3

9:35 pm-11:15 pm

Nonstop2h 40m

Chicago Midway

Sun 10/5

6:05 am-9:20 am

Nonstop2h 15m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 8/20

6:00 am-7:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Wed 8/27

8:40 am-12:04 pm

Nonstop2h 24m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 8/20

3:37 pm-10:22 pm

1 stop7h 45m

Chicago O'Hare Intl

Wed 8/27

11:36 am-11:49 pm

1 stop11h 13m

$138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/30

5:20 am-11:50 am

1 stop7h 30m

Chicago O'Hare Intl

Wed 9/3

6:00 am-5:05 pm

2 stops10h 05m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 8/5

7:20 am-9:18 am

Nonstop2h 58m

Chicago O'Hare Intl

Fri 8/8

7:10 pm-10:50 pm

Nonstop2h 40m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 8/22

6:16 pm-8:10 pm

Nonstop2h 54m

Chicago O'Hare Intl

Sun 8/24

6:30 am-9:56 am

Nonstop2h 26m

$155

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 8/18

5:28 am-7:24 am

Nonstop2h 56m

Chicago O'Hare Intl

Sat 8/23

5:32 pm-8:53 pm

Nonstop2h 21m

$165

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 9/5

8:59 am-4:43 pm

1 stop8h 44m

Chicago Midway

Mon 9/8

7:50 pm-9:43 am

1 stop12h 53m

$201

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/11

6:49 pm-4:43 pm

2 stops22h 54m

Chicago Midway

Mon 9/15

7:50 pm-9:43 am

1 stop12h 53m

$239

BostonPeoria

BOS - PIA

BOSPIA

Boston Logan Intl

Mon 7/28

9:32 am-2:58 pm

1 stop6h 26m

Greater Peoria

Fri 8/1

9:06 pm-11:48 pm

2 stops25h 42m

$242

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/13

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 July 14, 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 July 14, 2025.

The most flights from BOS to USIL are scheduled on a Monday (78 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (46 on average).

How much does it cost to fly round-trip from Boston to Illinois?

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 July 14, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

EUG - SEA

Mobility support was fabulous No flight entertainment that I was aware of.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

EUG - SEA

Mobility support was fabulous No flight entertainment that I was aware of.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

EUG - SEA

Mobility support was fabulous No flight entertainment that I was aware of.
Delta
8.0
Very good
7,956 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

EUG - SEA

Mobility support was fabulous No flight entertainment that I was aware of.
United Airlines
7.4
Good
8,858 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

EUG - SEA

Mobility support was fabulous No flight entertainment that I was aware of.
JetBlue
7.3
Good
2,908 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

EUG - SEA

Mobility support was fabulous No flight entertainment that I was aware of.

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.

  • 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 Spirit Airlines ($64), Southwest ($69), and United Airlines ($69).

  • 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 Avianca (95%), TAP AIR PORTUGAL (95%) or Cathay Pacific (95%) 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 $1,177, our data shows the cheapest flight currently is $68. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay $114 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 July 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$119FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$73Average$202FlexibilityNo cancel feeOn-time62%
DeltaCheapest$95Average$358FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$97Average$449FlexibilityNo cancel feeOn-time69%
FrontierCheapest$100Average$120FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$125Average$266FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$136Average$415FlexibilityNo cancel feeOn-time71%

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