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$64+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
feb. 20 — feb. 271
vie. 2/20
vie. 2/27
1 adult, Economy
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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 enero 21, 2026.

This JetBlue deal was found by Cheapflights users on 1/19. 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.
sáb. 2/77:40 am
ORD
-
BOS
Nonstop2h 25m
JetBlue
mar. 2/101:40 pm
BOS
-
ORD
1 stop6h 51m
JetBlue
Deal found 1/19$132
This Southwest deal was found by Cheapflights users on 1/20. 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.
sáb. 2/76:25 am
MDW
-
BOS
1 stop4h 55m
Southwest
dom. 2/85:30 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 1/20$132
This flygcity.se deal was found by Cheapflights users on 1/20. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 2/77:40 am
ORD
-
BOS
Nonstop2h 25m
JetBlue
dom. 2/81:40 pm
BOS
-
ORD
1 stop6h 51m
JetBlue
Deal found 1/20$134
This United Airlines deal was found by Cheapflights users on 1/20. 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.
vie. 1/237:30 am
ORD
-
BOS
Nonstop2h 22m
United Airlines
dom. 1/256:00 am
BOS
-
ORD
Nonstop3h 04m
United Airlines
Deal found 1/20$135
This Southwest deal was found by Cheapflights users on 1/20. 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.
vie. 1/305:35 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
dom. 2/15:20 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 1/20$135
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 2/144:42 pm
ORD
-
BOS
1 stop6h 47m
Multiple Airlines
mar. 2/175:50 pm
BOS
-
ORD
1 stop16h 49m
Multiple Airlines
Deal found 1/21$136
This JetBlue deal was found by Cheapflights users on 1/19. 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.
mié. 1/287:40 am
ORD
-
BOS
Nonstop2h 25m
JetBlue
mié. 2/43:35 pm
BOS
-
ORD
Nonstop3h 08m
JetBlue
Deal found 1/19$137
This Southwest deal was found by Cheapflights users on 1/21. 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.
jue. 2/56:35 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
dom. 2/85:30 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 1/21$137
This United Airlines deal was found by Cheapflights users on 1/21. 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.
sáb. 3/146:15 pm
ORD
-
BOS
Nonstop2h 28m
United Airlines
vie. 3/2011:02 am
BOS
-
ORD
Nonstop3h 05m
United Airlines
Deal found 1/21$138
This JetBlue deal was found by Cheapflights users on 1/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/126:20 pm
ORD
-
BOS
Nonstop2h 33m
JetBlue
dom. 3/226:00 pm
BOS
-
ORD
1 stop5h 56m
JetBlue
Deal found 1/21$140
This Trip.com deal was found by Cheapflights users on 1/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 2/77:40 am
ORD
-
BOS
Nonstop2h 25m
Multiple Airlines
dom. 2/87:00 am
BOS
-
ORD
1 stop11h 52m
Multiple Airlines
Deal found 1/21$141
This Southwest deal was found by Cheapflights users on 1/20. 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.
vie. 2/66:35 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
lun. 2/95:45 pm
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 1/20$141

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 enero 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$132
(JetBlue)

One-way from

$64
(Travelocity)

Popular in

April

Cheapest in

January

Average price

$207

Good round-trip deal

$164 or less

Good one-way deal

$78 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. 6% potential increase in price ($16 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 January 2026
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 enero 21, 2026.
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

sáb. 2/7

6:25 am-12:20 pm

1 stop4h 55m

Boston Logan Intl

dom. 2/8

5:30 am-7:20 am

Nonstop2h 50m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

lun. 3/2

7:05 am-10:37 am

Nonstop2h 32m

Boston Logan Intl

lun. 3/2

7:45 pm-9:48 pm

Nonstop3h 03m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 3/25

11:00 am-2:24 pm

Nonstop2h 24m

Boston Logan Intl

lun. 3/30

3:20 pm-5:24 pm

Nonstop3h 04m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

lun. 2/2

2:25 pm-5:54 pm

Nonstop2h 29m

Boston Logan Intl

mié. 2/4

4:10 pm-6:19 pm

Nonstop3h 09m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 1/31

7:40 am-11:05 am

Nonstop2h 25m

Boston Logan Intl

jue. 2/5

3:35 pm-5:43 pm

Nonstop3h 08m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 4/10

10:00 am-1:27 pm

Nonstop2h 27m

Boston Logan Intl

lun. 4/13

7:10 am-9:10 am

Nonstop3h 00m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 1/29

7:40 am-11:05 am

Nonstop2h 25m

Boston Logan Intl

mar. 2/3

3:35 pm-5:43 pm

Nonstop3h 08m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 1/31

7:40 am-11:05 am

Nonstop2h 25m

Boston Logan Intl

mié. 2/4

3:35 pm-5:43 pm

Nonstop3h 08m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 3/10

6:05 pm-9:28 pm

Nonstop2h 23m

Boston Logan Intl

sáb. 3/14

7:34 pm-11:44 pm

1 stop5h 10m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 2/28

9:17 am-12:46 pm

Nonstop2h 29m

Boston Logan Intl

dom. 3/1

5:30 am-9:34 am

1 stop5h 04m

$142

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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, September is the cheapest month in which you can book a flight from Illinois to Boston (average of $91). Flying from Illinois to Boston in February is currently the most expensive (average of $133). 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 enero 21, 2026.

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 19% 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 January 17, 2026.

Travelers seeking maximum savings on their Illinois to Boston flight should consider departing on Saturday afternoons 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 enero 21, 2026.

The most flights from USIL to BOS are scheduled on a Thursday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 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 24m. Your travel time can differ by up to 2h 31m. 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 $50. Spirit Airlines flights start at $57 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 Lambert-St Louis - Boston Logan Intl or Chicago Midway - 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 (86%), WestJet (85%), Air France (80%).

  • What are the cheapest flights from Illinois to Boston?

    The cheapest flight price from Illinois to Boston is $68. On average you can expect to pay $588. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $88.

  • 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, September is the cheapest month in which you can book a flight from Illinois to Boston (average of $91). Flying from Illinois to Boston in February is currently the most expensive (average of $133). 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
Seekonk
Brockton
Warwick
Seabrook
Cranston
Lincoln
Smithfield
Peabody
Quincy
York Beach
Londonderry
Swansea
Old Orchard Beach
Waltham
Lowell
Chelsea

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Top 6 airlines flying from Illinois to Boston

Discover the top 6 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 enero 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$61Average$157FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$79Average$158FlexibilityNo cancel feeOn-time65%
DeltaCheapest$94Average$218FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$117Average$370FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$117Average$461FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$136Average$245FlexibilityNo cancel feeOn-time63%

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