HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Boston

$63+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to Boston with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 December 23, 2025.

This JetBlue deal was found by Cheapflights users on 12/22. 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 12/317:41 pmORD - BOS
Nonstop2h 29mJetBlue
Tue 1/67:45 amBOS - ORD
Nonstop3h 11mJetBlue
Deal found 12/22$132
This United Airlines deal was found by Cheapflights users on 12/21. 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 12/256:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Fri 1/26:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/21$137
This United Airlines deal was found by Cheapflights users on 12/22. 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 12/309:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Fri 1/26:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/22$154
This United Airlines deal was found by Cheapflights users on 12/22. 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 12/317:45 amORD - BOS
Nonstop2h 23mUnited Airlines
Fri 1/26:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/22$157
This United Airlines deal was found by Cheapflights users on 12/21. 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 12/246:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Wed 12/314:15 pmBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/21$163
This Southwest deal was found by Cheapflights users on 12/21. 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 12/2511:25 amMDW - BOS
1 stop4h 55mSouthwest
Thu 1/110:20 amBOS - MDW
1 stop8h 15mSouthwest
Deal found 12/21$172
This United Airlines deal was found by Cheapflights users on 12/21. 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 12/246:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Thu 1/15:20 amBOS - ORD
1 stop5h 18mUnited Airlines
Deal found 12/21$177
This Southwest deal was found by Cheapflights users on 12/21. 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 12/265:30 amMDW - BOS
Nonstop2h 15mSouthwest
Sat 1/35:20 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 12/21$181
This Southwest deal was found by Cheapflights users on 12/22. 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 12/241:45 pmORD - BOS
1 stop7h 30mSouthwest
Sat 1/105:10 amBOS - ORD
1 stop8h 05mSouthwest
Deal found 12/22$186
This Southwest deal was found by Cheapflights users on 12/22. 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 12/2511:25 amMDW - BOS
1 stop4h 55mSouthwest
Fri 1/25:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 12/22$187
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Thu 12/257:11 amORD - BOS
1 stop5h 25mAmerican Airlines
Thu 1/16:36 amBOS - ORD
Nonstop3h 11mAmerican Airlines
Deal found 12/21$192
This Southwest deal was found by Cheapflights users on 12/21. 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 12/2412:55 pmMDW - BOS
1 stop5h 15mSouthwest
Thu 1/110:20 amBOS - MDW
1 stop5h 35mSouthwest
Deal found 12/21$202

Find flight deals from Illinois to Boston

Keep the following information in mind while searching for Illinois to Boston flight deals. Data was last updated December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$126
(Southwest)

One-way from

$63
(Cheapflightsfares)

Popular in

April

Cheapest in

January

Average price

$267

Good round-trip deal

$157 or less

Good one-way deal

$90 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
Search Deals
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. 5% potential increase in price ($13 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 December 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.
Search Deals

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 December 23, 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

Sat 1/10

8:40 am-4:10 pm

1 stop6h 30m

Boston Logan Intl

Sat 1/17

4:55 pm-6:45 pm

Nonstop2h 50m

$126

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 1/17

6:40 am-12:20 pm

1 stop4h 40m

Boston Logan Intl

Sun 1/18

5:30 am-7:20 am

Nonstop2h 50m

$128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 1/20

10:35 am-2:00 pm

Nonstop2h 25m

Boston Logan Intl

Tue 1/27

9:30 am-11:34 am

Nonstop3h 04m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 1/21

10:48 am-11:19 pm

1 stop11h 31m

Boston Logan Intl

Wed 1/28

5:23 pm-8:18 am

1 stop15h 55m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/29

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Sun 2/1

3:20 pm-5:25 pm

Nonstop3h 05m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/17

7:05 am-10:40 am

Nonstop2h 35m

Boston Logan Intl

Sun 1/18

7:30 am-9:41 am

Nonstop3h 11m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/31

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Sun 2/1

3:20 pm-5:25 pm

Nonstop3h 05m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/25

9:12 pm-12:45 am

Nonstop2h 33m

Boston Logan Intl

Thu 1/1

7:45 am-9:49 am

Nonstop3h 04m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/15

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Mon 1/19

3:35 pm-5:43 pm

Nonstop3h 08m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 3/7

9:15 pm-12:36 am

Nonstop2h 21m

Boston Logan Intl

Mon 3/9

4:30 pm-6:35 pm

Nonstop3h 05m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 60 results
1
2
3
...
6

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 $88). 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 December 23, 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 66% 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 December 23, 2025.

The most flights from USIL to BOS are scheduled on a Friday (57 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (18 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, United Airlines, and Spirit Airlines can get you from Illinois to Boston in just under 2h 25m. Your travel time can differ by up to 9h 06m. The distance from Illinois to Boston is about 864 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $55. Spirit Airlines flights start at $55 while deals on Southwest start at $58 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: Etihad Airways (79%), Envoy Air (78%), Avianca (73%).

  • What are the cheapest flights from Illinois to Boston?

    The cheapest flight price from Illinois to Boston is $63. On average you can expect to pay $721. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $120.

  • 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 $88). 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
Brockton
Cranston
Lincoln
Lowell
Smithfield
Peabody
Quincy
York Beach
Warwick
Londonderry
Swansea
Old Orchard Beach
Waltham
Chelsea

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Illinois to Boston

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to Boston flights
Los Angeles to Boston flights
Atlanta to Boston flights
San Francisco to Boston flights
Reagan-National to Boston flights
Baltimore to Boston flights
Seattle to Boston flights
O'Hare Intl to Boston flights
Tampa to Boston flights
Dulles Intl to Boston flights
Denver to Boston flights
Philadelphia to Boston flights
Newark to Boston flights
Raleigh to Boston flights
Fort Lauderdale to Boston flights
LaGuardia to Boston flights
Hobby to Boston flights
Orlando to Boston flights
Austin to Boston flights
Miami to Boston flights
Charlotte to Boston flights
George Bush Intcntl to Boston flights
Minneapolis to Boston flights
West Palm Beach to Boston flights
John F Kennedy Intl to Boston flights
Cleveland to Boston flights
Orlando to Hartford flights
Detroit to Boston flights
Portland to Boston flights
Pittsburgh to Boston flights
Cincinnati to Boston flights
Columbus to Boston flights
Sky Harbor Intl to Boston flights
Fort Myers to Boston flights
Nashville to Boston flights
Jacksonville to Boston flights
Ontario to Boston flights
San Diego to Boston flights
Indianapolis to Boston flights
Salt Lake City to Boston flights
Midway to Boston flights
San Antonio to Boston flights
Kansas City to Boston flights
Dulles Intl to Hartford flights
Los Angeles to Hartford flights
Love Field to Boston flights
Richmond to Boston flights
Dallas/Fort Worth to Hartford flights
Sarasota to Boston flights
New Orleans to Boston flights

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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$78Average$175FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$166FlexibilityNo cancel feeOn-time65%
DeltaCheapest$103Average$225FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$104Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$117Average$459FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$117Average$377FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$135Average$248FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.