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$60+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 October 28, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$118
(Flysmarter)

One-way from

$60
(Flysmarter)

Popular in

April

Cheapest in

September

Average price

$247

Good round-trip deal

$200 or less

Good one-way deal

$131 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
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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 ($24 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 October 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 October 28, 2025.

This Flysmarter deal was found by Cheapflights users on 10/26. 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.
Thu 11/138:30 amBOS - ORD
Nonstop3h 05mJetBlue
Sat 11/1510:00 amORD - BOS
Nonstop2h 20mJetBlue
Deal found 10/26$118
This Mytrip deal was found by Cheapflights users on 10/27. 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 11/109:55 amBOS - MDW
1 stop9h 44mFrontier
Thu 11/1310:12 amMDW - BOS
1 stop21h 16mFrontier
Deal found 10/27$119
This Delta deal was found by Cheapflights users on 10/27. 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 12/44:05 pmBOS - ORD
Nonstop2h 57mDelta
Sun 12/77:10 amORD - BOS
Nonstop2h 26mDelta
Deal found 10/27$119
This Flightnetwork deal was found by Cheapflights users on 10/27. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/108:40 amBOS - ORD
1 stop15h 48mFrontier
Thu 11/135:25 amORD - BOS
1 stop26h 03mFrontier
Deal found 10/27$120
This JetBlue deal was found by Cheapflights users on 10/26. 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.
Thu 11/209:40 amBOS - ORD
Nonstop3h 03mJetBlue
Thu 11/2712:28 pmORD - BOS
Nonstop2h 26mJetBlue
Deal found 10/26$122
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1111:28 amBOS - MDW
1 stop7h 40mFrontier
Thu 12/186:12 amMDW - BOS
1 stop18h 07mFrontier
Deal found 10/27$123
This Orbitz deal was found by Cheapflights users on 10/26. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1511:43 amBOS - ORD
1 stop12h 46mMultiple Airlines
Tue 11/183:26 pmORD - BOS
1 stop7h 33mMultiple Airlines
Deal found 10/26$123
This Delta deal was found by Cheapflights users on 10/27. 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 12/1112:50 pmBOS - ORD
Nonstop2h 57mDelta
Fri 12/197:10 amORD - BOS
Nonstop2h 26mDelta
Deal found 10/27$124
This Southwest deal was found by Cheapflights users on 10/27. 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 11/95:15 amBOS - MDW
Nonstop2h 45mSouthwest
Thu 11/139:35 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 10/27$127
This JetBlue deal was found by Cheapflights users on 10/28. 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 11/157:10 amBOS - ORD
Nonstop3h 05mJetBlue
Mon 11/176:55 pmORD - BOS
Nonstop2h 32mJetBlue
Deal found 10/28$127
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1111:28 amBOS - MDW
1 stop7h 40mFrontier
Sun 12/146:15 amMDW - BOS
1 stop27h 07mFrontier
Deal found 10/26$128
This JetBlue deal was found by Cheapflights users on 10/27. 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.
Mon 11/103:55 pmBOS - ORD
Nonstop3h 00mJetBlue
Wed 11/126:55 pmORD - BOS
Nonstop2h 32mJetBlue
Deal found 10/27$130

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 October 28, 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

Thu 12/4

4:05 pm-6:02 pm

Nonstop2h 57m

Chicago O'Hare Intl

Sun 12/7

7:10 am-10:36 am

Nonstop2h 26m

$119

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 11/5

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Wed 11/12

6:55 pm-10:27 pm

Nonstop2h 32m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 11/6

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sun 11/9

6:15 am-9:30 am

Nonstop2h 15m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 11/10

3:55 pm-5:55 pm

Nonstop3h 00m

Chicago O'Hare Intl

Wed 11/12

6:55 pm-10:27 pm

Nonstop2h 32m

$130

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 11/11

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Thu 11/13

11:20 am-2:44 pm

Nonstop2h 24m

$130

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 11/10

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Thu 11/13

11:20 am-2:44 pm

Nonstop2h 24m

$133

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 11/11

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

Sun 11/16

5:00 am-12:50 pm

1 stop6h 50m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 11/14

6:50 pm-11:30 pm

1 stop5h 40m

Chicago Midway

Sat 11/15

9:50 am-1:10 pm

Nonstop2h 20m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/21

4:10 pm-6:19 pm

Nonstop3h 09m

Chicago O'Hare Intl

Mon 1/26

2:24 pm-5:53 pm

Nonstop2h 29m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 11/19

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

Sat 11/22

4:05 pm-12:10 am

1 stop7h 05m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

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, November is the cheapest month in which you can book a flight from Boston to Illinois (average of $88). Flying from Boston to Illinois in December is currently the most expensive (average of $125). 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 October 28, 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 42% 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.

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 October 28, 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
4,240 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

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
7.9
Good
7,994 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

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
9,001 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

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
11,032 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

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
2,908 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

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 57m. There are 864 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 Southwest ($64), United Airlines ($64), and JetBlue ($64).

  • 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 TAP AIR PORTUGAL (88%), Icelandair (88%) 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 $717, our data shows the cheapest flight currently is $58. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay $91 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, November is the cheapest month in which you can book a flight from Boston to Illinois (average of $88). Flying from Boston to Illinois in December is currently the most expensive (average of $125). 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.

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Alternative routes for Boston to Illinois

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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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$67Average$227FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$75Average$195FlexibilityNo cancel feeOn-time62%
FrontierCheapest$89Average$116FlexibilityNo cancel feeOn-time62%
DeltaCheapest$116Average$291FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$117Average$238FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$129Average$495FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$136Average$429FlexibilityNo cancel feeOn-time71%

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