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Illinois

$57+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This United Airlines deal was found by Cheapflights users on 12/10. 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 12/316:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Mon 1/59:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/10$132
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Sat 12/136:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Mon 12/151:55 pmORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 12/10$137
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Mon 12/155:22 pmBOS - ORD
Nonstop3h 17mAmerican Airlines
Wed 12/178:40 pmORD - BOS
Nonstop2h 33mAmerican Airlines
Deal found 12/10$142
This United Airlines deal was found by Cheapflights users on 12/10. 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 12/176:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Wed 12/174:05 pmORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 12/10$145
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Tue 12/166:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Thu 12/186:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/10$152
This United Airlines deal was found by Cheapflights users on 12/10. 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 12/176:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Thu 12/189:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/10$155
This Southwest deal was found by Cheapflights users on 12/10. 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.
Sun 12/145:15 amBOS - MDW
Nonstop2h 45mSouthwest
Mon 12/156:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 12/10$157
This JetBlue deal was found by Cheapflights users on 12/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/148:30 amBOS - ORD
Nonstop3h 05mJetBlue
Mon 12/1511:25 amORD - BOS
Nonstop2h 24mJetBlue
Deal found 12/10$157
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Wed 12/176:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Thu 12/187:25 pmORD - BOS
Nonstop2h 37mAmerican Airlines
Deal found 12/10$162
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Mon 12/1510:40 amBOS - ORD
Nonstop3h 00mUnited Airlines
Mon 12/223:53 pmORD - BOS
1 stop5h 55mUnited Airlines
Deal found 12/10$167
This American Airlines deal was found by Cheapflights users on 12/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/166:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Mon 1/56:22 pmORD - BOS
Nonstop2h 32mAmerican Airlines
Deal found 12/9$172
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Tue 12/166:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Mon 1/56:21 pmORD - BOS
1 stop4h 33mUnited Airlines
Deal found 12/10$177

Find flight deals from Boston to Illinois

Keep the following information in mind while searching for Boston to Illinois flight deals. Data was last updated December 12, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$120
(SmartFares)

One-way from

$57
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$247

Good round-trip deal

$217 or less

Good one-way deal

$135 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 Boston Logan Intl to Illinois
Search Deals
One-way flight from Boston Logan Intl to Illinois
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Illinois.
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Illinois.
Search Deals

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 December 12, 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 - ORD

BOSORD

Boston Logan Intl

Sat 1/17

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Mon 1/19

7:45 am-11:10 am

Nonstop2h 25m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/16

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 1/18

7:45 am-11:10 am

Nonstop2h 25m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/17

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sun 1/18

2:35 pm-9:45 pm

1 stop6h 10m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 2/7

5:15 pm-7:26 pm

Nonstop3h 11m

Chicago O'Hare Intl

Tue 2/10

2:25 pm-5:54 pm

Nonstop2h 29m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/2

6:01 am-8:05 am

Nonstop3h 04m

Chicago O'Hare Intl

Mon 1/5

9:12 pm-12:45 am

Nonstop2h 33m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/9

2:40 pm-4:30 pm

Nonstop2h 50m

Chicago Midway

Wed 1/14

2:00 pm-5:10 pm

Nonstop2h 10m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/9

7:55 pm-10:01 pm

Nonstop3h 06m

Chicago O'Hare Intl

Sun 1/11

7:05 am-10:40 am

Nonstop2h 35m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/23

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sun 1/25

6:35 pm-9:50 pm

Nonstop2h 15m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/17

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 1/18

7:45 am-11:10 am

Nonstop2h 25m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/14

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 1/18

7:45 am-11:10 am

Nonstop2h 25m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

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, April is the cheapest month in which you can book a flight from Boston to Illinois (average of $89). Flying from Boston to Illinois in January is currently the most expensive (average of $119). 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 December 12, 2025.

One of the essential ways to save on airfare from Boston to Illinois is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 43% on airfare.

What is the cheapest day to fly from Boston to Illinois?

Use this chart to determine the cheapest time to fly round-trip from Boston to Illinois. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Boston to Illinois flight should consider departing on Thursday mornings 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 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 December 12, 2025.

The most flights from BOS to USIL are scheduled on a Thursday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 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 December 12, 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
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,007 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,095 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,050 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,899 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 50m. There are 857 mi between Boston and Illinois. Most flights are nonstop.

  • 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 ($46), Frontier ($47), and Southwest ($58).

  • 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 ANA (84%), TAP AIR PORTUGAL (83%) or JetBlue (81%) 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 $772, our data shows the cheapest flight currently is $65. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay $112 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, April is the cheapest month in which you can book a flight from Boston to Illinois (average of $89). Flying from Boston to Illinois in January is currently the most expensive (average of $119). 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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Top 6 airlines flying from Boston to Illinois

Discover the top 6 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$78Average$189FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$350FlexibilityNo cancel feeOn-time65%
DeltaCheapest$114Average$288FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$117Average$236FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$124Average$449FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$131Average$424FlexibilityNo cancel feeOn-time71%

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