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$46+ Cheap flights from Illinois to Boston (BOS)

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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Dec 7 — Dec 141
Sun 12/7
Sun 12/14
1 adult, Economy
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Find flight deals from Illinois to Boston

Cheapest flights from Illinois to Boston
Explore the most affordable flight options available from Illinois to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 7, 2025.

This Delta deal was found by Cheapflights users on 11/5. 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.
Fri 12/53:50 pmORD - BOS
Nonstop2h 24mDelta
Sun 12/712:50 pmBOS - ORD
Nonstop2h 57mDelta
Deal found 11/5$117
This Southwest deal was found by Cheapflights users on 11/5. 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 12/56:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Sun 12/75:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/5$117
This Southwest deal was found by Cheapflights users on 11/6. 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 11/271:40 pmMDW - BOS
Nonstop2h 15mSouthwest
Wed 12/312:20 pmBOS - MDW
1 stop6h 30mSouthwest
Deal found 11/6$118
This Trip.com deal was found by Cheapflights users on 11/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:38 pmORD - BOS
Nonstop2h 28mJetBlue
Sun 12/78:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 11/6$119
This Southwest deal was found by Cheapflights users on 11/6. 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 12/49:25 amMDW - BOS
1 stop6h 55mSouthwest
Mon 12/86:00 pmBOS - MDW
1 stop5h 35mSouthwest
Deal found 11/6$119
This Trip.com deal was found by Cheapflights users on 11/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:25 amORD - BOS
Nonstop2h 24mJetBlue
Mon 12/85:29 pmBOS - ORD
Nonstop3h 14mJetBlue
Deal found 11/5$120
This Southwest deal was found by Cheapflights users on 11/5. 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 12/46:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Fri 12/55:30 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/5$122
This United Airlines deal was found by Cheapflights users on 11/6. 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 11/259:25 pmORD - BOS
Nonstop2h 20mUnited Airlines
Wed 12/36:23 pmBOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 11/6$123
This Southwest deal was found by Cheapflights users on 11/7. 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 12/56:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Mon 12/86:00 pmBOS - MDW
1 stop5h 35mSouthwest
Deal found 11/7$123
This JetBlue deal was found by Cheapflights users on 11/4. 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 12/247:41 pmORD - BOS
Nonstop2h 29mJetBlue
Wed 12/314:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 11/4$124
This Southwest deal was found by Cheapflights users on 11/7. 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 12/212:25 pmMDW - BOS
1 stop8h 50mSouthwest
Thu 12/47:20 amBOS - MDW
1 stop5h 05mSouthwest
Deal found 11/7$124
This Trip.com deal was found by Cheapflights users on 11/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1510:00 amORD - BOS
Nonstop2h 20mJetBlue
Mon 11/173:55 pmBOS - ORD
Nonstop3h 00mJetBlue
Deal found 11/7$125

Cheap flight deals from Illinois to Boston

Keep the following information in mind while searching for Illinois to Boston flight deals. Data was last updated November 7, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Delta)

One-way from

$46
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$230

Good round-trip deal

$150 or less

Good one-way deal

$93 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
Search Deals
From Illinois to Boston Logan Intl
Search Deals
One-way flight from Illinois to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Illinois to Boston Logan Intl.
Search Deals
Price to beat on a one-way flight from Illinois to Boston Logan Intl.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Boston 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 November 7, 2025.
Use the filters below to find and compare flights from Illinois to Boston that are best for you.

Fly from

Illinois

Fly to

Boston

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/5

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Sun 12/7

5:15 am-7:00 am

Nonstop2h 45m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/4

9:25 am-5:20 pm

1 stop6h 55m

Boston Logan Intl

Sun 12/7

5:15 am-7:00 am

Nonstop2h 45m

$118

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/4

11:25 am-5:20 pm

1 stop4h 55m

Boston Logan Intl

Mon 12/8

6:00 pm-10:35 pm

1 stop5h 35m

$119

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/5

9:25 am-5:20 pm

1 stop6h 55m

Boston Logan Intl

Sat 12/6

5:20 am-7:05 am

Nonstop2h 45m

$123

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/4

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Fri 12/5

10:20 am-2:55 pm

1 stop5h 35m

$123

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 12/8

8:38 pm-12:06 am

Nonstop2h 28m

Boston Logan Intl

Sat 12/13

3:40 pm-9:52 pm

1 stop7h 12m

$126

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 11/13

10:48 am-2:08 pm

Nonstop2h 20m

Boston Logan Intl

Sun 11/16

6:00 am-8:00 am

Nonstop3h 00m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 12/6

1:16 pm-7:33 pm

1 stop5h 17m

Boston Logan Intl

Sun 12/7

12:50 pm-2:47 pm

Nonstop2h 57m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 12/7

7:10 am-10:36 am

Nonstop2h 26m

Boston Logan Intl

Sat 12/13

9:15 am-3:20 pm

1 stop7h 05m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/5

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Fri 12/12

6:50 pm-11:30 pm

1 stop5h 40m

$127

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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

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

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

Currently, November is the cheapest month in which you can book a flight from Illinois to Boston (average of $71). Flying from Illinois to Boston in February is currently the most expensive (average of $137). 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 IL to BOS?

Find hourly flight availability from Illinois to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 7, 2025.

When flying from Illinois to Boston, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 64% versus a flight at noon.

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

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

Travelers seeking maximum savings on their Illinois to Boston flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Illinois to Boston

Explore weekly flight availability from Illinois to Boston. 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 November 7, 2025.

The most flights from USIL to BOS are scheduled on a Friday (70 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).

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

Related info for your journey

Find useful and relevant information for your journey from Illinois to Boston. 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 into for flights to Boston from Illinois?

    Located just 2.6 mi from the city center, Boston Logan Intl (BOS) is the airport most travelers will use when flying to Boston from Illinois.

  • How long is the flight from Illinois to Boston?

    Southwest, JetBlue, and United Airlines can get you from Illinois to Boston in just under 2h 20m. Your travel time will be generally consistent. The distance from Illinois to Boston is about 857 mi. Generally, flights for this route are nonstop.

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

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $59. United Airlines flights start at $59 while deals on Southwest start at $59 one-way.

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

    The most popular route from Illinois to Boston is Chicago O'Hare Intl - Boston Logan Intl. You may also consider Chicago Midway - Boston Logan Intl or Lambert-St Louis - Boston Logan Intl.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Illinois to Boston on time: Envoy Air (81%), Etihad Airways (72%), Virgin Atlantic (71%).

  • What are the cheapest flights from Illinois to Boston?

    The cheapest flight price from Illinois to Boston is $58. On average you can expect to pay $966. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $99.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Illinois to Boston (average of $71). Flying from Illinois to Boston in February is currently the most expensive (average of $137). 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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Peabody
Quincy
York Beach
Warwick
Swansea
Old Orchard Beach
Brockton
Waltham
Chelsea

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Top 7 airlines flying from Illinois to Boston

Discover the top 7 airlines that operate flights from Illinois to Boston. 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 November 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$68Average$151FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$76Average$183FlexibilityNo cancel feeOn-time62%
DeltaCheapest$102Average$230FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$104Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$117Average$463FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$118Average$400FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$137Average$250FlexibilityNo cancel feeOn-time63%

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