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$62+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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Cheap flight deals from Boston to Illinois

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Illinois (USIL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2024.

Round-trip from

$137
(Trip.com)

One-way from

$62
(Mytrip)
From Boston Logan Intl to Illinois
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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 December 18, 2024.

This CheapOair deal was found by Cheapflights users on 12/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:27 amBOS - ORD
1 stop17h 16mMultiple Airlines
Thu 1/95:02 pmORD - BOS
1 stop6h 28mMultiple Airlines
Deal found 12/17$155
This FlightHub deal was found by Cheapflights users on 12/16. 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.
Thu 12/1912:25 pmBOS - MDW
1 stop12h 53mFrontier
Mon 12/239:59 pmMDW - BOS
1 stop8h 02mFrontier
Deal found 12/16$177
This FlightHub deal was found by Cheapflights users on 12/16. 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 12/1811:10 amBOS - ORD
1 stop11h 17mFrontier
Sun 12/2210:14 pmORD - BOS
1 stop8h 19mFrontier
Deal found 12/16$181
This JetBlue deal was found by Cheapflights users on 12/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:10 amBOS - ORD
Nonstop3h 00mJetBlue
Wed 1/89:10 amORD - BOS
Nonstop2h 30mJetBlue
Deal found 12/17$182
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/317:42 pmBOS - ORD
1 stop4h 43mUnited Airlines
Tue 1/72:00 pmORD - BOS
Nonstop2h 23mUnited Airlines
Deal found 12/17$183
This American Airlines deal was found by Cheapflights users on 12/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:45 amBOS - ORD
Nonstop3h 04mAmerican Airlines
Tue 1/76:45 pmORD - BOS
Nonstop2h 27mAmerican Airlines
Deal found 12/17$193
This Southwest deal was found by Cheapflights users on 12/17. 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.
Tue 12/317:00 amBOS - MDW
Nonstop2h 45mSouthwest
Tue 1/710:05 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 12/17$194
This Mytrip deal was found by Cheapflights users on 12/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/319:54 pmBOS - ORD
2 stops19h 12mSpirit Airlines
Tue 1/71:24 pmORD - BOS
1 stop8h 51mSpirit Airlines
Deal found 12/17$210
This Gotogate deal was found by Cheapflights users on 12/18. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:00 amBOS - STL
1 stop18h 28mFrontier
Tue 1/75:05 pmSTL - BOS
1 stop6h 25mFrontier
Deal found 12/18$217
This Delta deal was found by Cheapflights users on 12/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/259:00 amBOS - ORD
Nonstop3h 03mDelta
Fri 1/37:35 amORD - BOS
Nonstop2h 28mDelta
Deal found 12/17$223
This Delta deal was found by Cheapflights users on 12/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/315:25 amBOS - MDW
1 stop4h 25mDelta
Sat 1/49:30 amMDW - BOS
1 stop5h 55mDelta
Deal found 12/17$316
This Southwest deal was found by Cheapflights users on 12/17. 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.
Tue 12/3111:05 amBOS - ORD
2 stops11h 55mSouthwest
Sun 1/52:55 pmORD - BOS
2 stops8h 25mSouthwest
Deal found 12/17$338

Find flights from Boston to Illinois within your budget

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 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/9

12:05 pm-12:11 pm

1 stop25h 06m

Chicago Midway

Sun 1/12

10:58 am-12:30 am

1 stop12h 32m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/17

11:46 am-8:45 pm

1 stop9h 59m

Chicago O'Hare Intl

Wed 1/22

1:45 pm-12:39 am

1 stop9h 54m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/22

6:00 am-12:45 pm

1 stop7h 45m

Chicago O'Hare Intl

Sat 1/25

12:37 pm-9:44 pm

1 stop8h 07m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 5/6

7:00 am-4:52 pm

1 stop10h 52m

Chicago O'Hare Intl

Sat 5/10

6:15 am-10:12 pm

1 stop14h 57m

$143

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/9

3:30 pm-5:36 pm

Nonstop3h 06m

Chicago O'Hare Intl

Sun 1/12

7:10 am-10:47 am

Nonstop2h 37m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/9

5:40 pm-7:30 pm

Nonstop2h 50m

Chicago Midway

Wed 1/15

10:05 am-1:20 pm

Nonstop2h 15m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/9

2:52 pm-4:52 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sun 1/12

8:05 am-11:26 am

Nonstop2h 21m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/31

11:28 am-5:18 pm

1 stop6h 50m

Chicago O'Hare Intl

Fri 2/7

9:05 am-12:23 pm

Nonstop2h 18m

$166

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/1

6:02 am-8:05 am

Nonstop3h 03m

Chicago O'Hare Intl

Tue 1/7

7:30 am-10:56 am

Nonstop2h 26m

$173

BostonSt. Louis

BOS - STL

BOSSTL

Boston Logan Intl

Thu 1/16

6:00 am-2:43 pm

1 stop9h 43m

Lambert-St Louis

Wed 1/22

5:05 pm-12:27 am

1 stop6h 22m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 59 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.

Travel insights for flights from Boston to Illinois

Get recent, data-driven insights about flights from Boston to Illinois including ideal travel times, pricing trends, and more.

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

Currently, September is the cheapest month in which you can book a flight from Boston to Illinois (average of $232). Flying from Boston to Illinois in June is currently the most expensive (average of $308). 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 18, 2024.

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.

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 18, 2024.
Get a feel of what it's like to fly with Spirit Airlines, Delta and American Airlines from Boston to Illinois by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,554 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,279 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,055 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier ($62), Southwest ($79), and JetBlue ($79).

  • 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 (98%), Japan Airlines (95%) or Spirit Airlines (94%) 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 $918, our data shows the cheapest flight currently is $78. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay $105 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, September is the cheapest month in which you can book a flight from Boston to Illinois (average of $232). Flying from Boston to Illinois in June is currently the most expensive (average of $308). 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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$105FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$81Average$232FlexibilityNo cancel feeOn-time62%
DeltaCheapest$93Average$345FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$98Average$144FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$137Average$485FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$494FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$148Average$294FlexibilityNo cancel feeOn-time63%
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