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$69+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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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 September 16, 2025.

Round-trip from

$127
(JetBlue)

One-way from

$69
(United Airlines)

Popular in

April

Cheapest in

September

Average price

$207

Good round-trip deal

$168 or less

Good one-way deal

$68 or less
From Illinois to Boston Logan Intl
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One-way flight from Illinois to Boston Logan Intl
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Highest demand for flights based on searches. 6% potential increase in price ($14 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 September 2025
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Price to beat on a round-trip flight from Illinois to Boston Logan Intl.
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Price to beat on a one-way flight from Illinois to Boston Logan Intl.
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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 September 16, 2025.

This JetBlue deal was found by Cheapflights users on 9/15. 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 9/297:50 pmORD - BOS
Nonstop2h 35mJetBlue
Sat 10/47:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 9/15$127
This Southwest deal was found by Cheapflights users on 9/15. 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 10/216:05 amMDW - BOS
Nonstop2h 15mSouthwest
Tue 10/215:05 pmBOS - MDW
1 stop8h 00mSouthwest
Deal found 9/15$127
This JetBlue deal was found by Cheapflights users on 9/15. 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 10/19:51 amORD - BOS
Nonstop2h 29mJetBlue
Wed 10/14:40 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 9/15$130
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:50 pmORD - BOS
Nonstop2h 35mJetBlue
Wed 10/17:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 9/14$132
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/79:30 amMDW - BOS
2 stops7h 45mSouthwest
Sun 11/95:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/16$132
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/11:30 pmORD - BOS
Nonstop2h 32mUnited Airlines
Sun 10/56:00 amBOS - ORD
Nonstop2h 57mUnited Airlines
Deal found 9/14$133
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/79:05 pmMDW - BOS
1 stop10h 00mSouthwest
Mon 11/105:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/16$133
This JetBlue deal was found by Cheapflights users on 9/15. 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 11/611:20 amORD - BOS
Nonstop2h 24mJetBlue
Wed 11/123:55 pmBOS - ORD
Nonstop3h 00mJetBlue
Deal found 9/15$135
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/86:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Wed 10/156:16 amBOS - ORD
1 stop18h 29mSpirit Airlines
Deal found 9/15$136
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2311:05 amORD - BOS
Nonstop2h 35mUnited Airlines
Wed 9/244:27 pmBOS - ORD
Nonstop2h 54mUnited Airlines
Deal found 9/16$137
This Southwest deal was found by Cheapflights users on 9/15. 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.
Wed 11/264:05 pmMDW - BOS
Nonstop2h 15mSouthwest
Fri 11/285:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/15$137
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/309:25 pmORD - BOS
Nonstop2h 20mUnited Airlines
Sat 11/16:26 pmBOS - ORD
Nonstop2h 59mUnited Airlines
Deal found 9/16$138

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 September 16, 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

Mon 10/20

9:20 pm-12:40 am

Nonstop2h 20m

Boston Logan Intl

Wed 10/22

1:35 pm-6:10 pm

1 stop5h 35m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 10/18

6:30 am-9:45 am

Nonstop2h 15m

Boston Logan Intl

Sat 10/25

6:30 am-4:25 pm

2 stops10h 55m

$132

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 11/15

1:15 pm-7:35 pm

1 stop5h 20m

Boston Logan Intl

Wed 11/19

5:35 pm-9:05 pm

1 stop4h 30m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 1/7

7:00 am-10:33 am

Nonstop2h 33m

Boston Logan Intl

Sun 1/11

7:00 am-9:10 am

Nonstop3h 10m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 12/13

11:25 am-2:49 pm

Nonstop2h 24m

Boston Logan Intl

Wed 12/17

8:30 am-10:35 am

Nonstop3h 05m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 11/26

1:06 pm-4:34 pm

Nonstop2h 28m

Boston Logan Intl

Sat 11/29

5:35 pm-7:50 pm

Nonstop3h 15m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 11/26

4:05 pm-7:20 pm

Nonstop2h 15m

Boston Logan Intl

Fri 11/28

5:15 am-7:00 am

Nonstop2h 45m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 9/29

6:45 pm-10:05 pm

Nonstop2h 20m

Boston Logan Intl

Tue 9/30

3:15 pm-4:50 pm

Nonstop2h 35m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 11/14

9:30 am-6:15 pm

2 stops7h 45m

Boston Logan Intl

Tue 11/18

5:35 pm-9:05 pm

1 stop4h 30m

$138

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 12/13

9:50 am-1:10 pm

Nonstop2h 20m

Boston Logan Intl

Wed 12/17

5:35 pm-9:05 pm

1 stop4h 30m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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, January is the cheapest month in which you can book a flight from Illinois to Boston (average of $218). Flying from Illinois to Boston in July is currently the most expensive (average of $311). 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 September 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Boston as you normally would.

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 September 16, 2025.

The most flights from USIL to BOS are scheduled on a Monday (73 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 on average).

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, Delta, and JetBlue 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 JetBlue, which is currently one of the cheapest options available, starting at $69. Southwest flights start at $69 while deals on Spirit Airlines start at $95 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 (96%), Air France (78%), Scandinavian Airlines (76%).

  • What are the cheapest flights from Illinois to Boston?

    The cheapest flight price from Illinois to Boston is $64. On average you can expect to pay $430. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $112.

  • 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, January is the cheapest month in which you can book a flight from Illinois to Boston (average of $218). Flying from Illinois to Boston in July is currently the most expensive (average of $311). 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
Chelsea
Warwick
Peabody
Quincy
York Beach
Swansea
Old Orchard Beach
Brockton
Waltham

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$37Average$152FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$78Average$184FlexibilityNo cancel feeOn-time62%
DeltaCheapest$95Average$228FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$118Average$461FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$132Average$403FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$141Average$262FlexibilityNo cancel feeOn-time63%

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