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$90+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Aug 11 — Aug 181
Tue 8/11
Tue 8/18
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 July 12, 2026.

This Southwest deal was found by Cheapflights users on 7/10. 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 8/207:55 pm
MDW
-
BOS
1 stop11h 05m
Southwest
Tue 8/255:25 am
BOS
-
MDW
1 stop4h 35m
Southwest
Deal found 7/10$167
This United Airlines deal was found by Cheapflights users on 7/8. 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 8/209:40 pm
ORD
-
BOS
Nonstop2h 31m
United Airlines
Sun 8/235:45 am
BOS
-
ORD
1 stop4h 53m
United Airlines
Deal found 7/8$168
This Southwest deal was found by Cheapflights users on 7/8. 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 7/292:40 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Thu 8/203:35 pm
BOS
-
MDW
1 stop6h 25m
Southwest
Deal found 7/8$168
This Cheapflightsfares deal was found by Cheapflights users on 7/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:20 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Sun 8/235:01 am
BOS
-
ORD
1 stop4h 51m
JetBlue
Deal found 7/8$169
This Southwest deal was found by Cheapflights users on 7/8. 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 8/112:00 pm
MDW
-
BOS
2 stops7h 10m
Southwest
Wed 8/127:15 pm
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 7/8$169
This United Airlines deal was found by Cheapflights users on 7/8. 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.
Sat 7/259:41 pm
ORD
-
BOS
Nonstop2h 33m
United Airlines
Wed 7/296:00 am
BOS
-
ORD
Nonstop2h 58m
United Airlines
Deal found 7/8$170
This Southwest deal was found by Cheapflights users on 7/8. 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 8/67:55 pm
MDW
-
BOS
1 stop11h 05m
Southwest
Tue 8/117:15 pm
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 7/8$170
This JetBlue deal was found by Cheapflights users on 7/8. 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.
Sat 8/151:55 pm
ORD
-
BOS
Nonstop2h 36m
JetBlue
Tue 8/182:45 pm
BOS
-
ORD
1 stop8h 13m
JetBlue
Deal found 7/8$171
This Southwest deal was found by Cheapflights users on 7/9. 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 8/73:20 pm
MDW
-
BOS
1 stop6h 00m
Southwest
Mon 8/108:20 pm
BOS
-
MDW
Nonstop2h 40m
Southwest
Deal found 7/9$171
This United Airlines deal was found by Cheapflights users on 7/8. 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.
Sat 8/13:55 pm
ORD
-
BOS
Nonstop2h 35m
United Airlines
Wed 8/55:45 am
BOS
-
ORD
1 stop4h 51m
United Airlines
Deal found 7/8$172
This Southwest deal was found by Cheapflights users on 7/10. 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.
Mon 8/248:05 am
MDW
-
BOS
2 stops5h 25m
Southwest
Mon 8/317:40 am
BOS
-
MDW
2 stops8h 15m
Southwest
Deal found 7/10$172
This Cheapflightsfares deal was found by Cheapflights users on 7/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:35 am
ORD
-
BOS
1 stop6h 32m
JetBlue
Wed 8/268:15 am
BOS
-
ORD
Nonstop2h 56m
JetBlue
Deal found 7/7$173

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 July 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$167
(Southwest)

One-way from

$90
(Southwest)

Popular in

April

Cheapest in

January

Average price

$245

Good round-trip deal

$211 or less

Good one-way deal

$133 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. 2% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 12, 2026.
Use the filters below to find and compare flights from Illinois to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 8/20

5:45 am-9:00 am

Nonstop2h 15m

Boston Logan Intl

Sat 8/22

5:50 am-1:05 pm

2 stops8h 15m

$174

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 9/14

1:00 pm-7:40 pm

2 stops5h 40m

Boston Logan Intl

Tue 9/15

1:20 pm-6:45 pm

1 stop6h 25m

$179

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 7/31

6:05 am-9:29 am

Nonstop2h 24m

Boston Logan Intl

Tue 8/4

7:27 pm-11:31 pm

1 stop5h 04m

$180

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 9/3

5:45 am-9:00 am

Nonstop2h 15m

Boston Logan Intl

Sun 9/6

7:55 am-5:25 pm

1 stop10h 30m

$181

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/30

1:00 pm-8:49 pm

1 stop6h 49m

Boston Logan Intl

Fri 10/2

6:55 am-8:46 am

Nonstop2h 51m

$183

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 10/2

9:24 pm-12:59 am

Nonstop2h 35m

Boston Logan Intl

Sun 10/4

8:00 am-9:56 am

Nonstop2h 56m

$187

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 7/31

9:41 pm-1:14 am

Nonstop2h 33m

Boston Logan Intl

Sun 8/2

6:00 am-7:58 am

Nonstop2h 58m

$195

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 7/31

5:27 pm-11:59 pm

1 stop5h 32m

Boston Logan Intl

Wed 8/5

4:30 pm-9:58 pm

1 stop6h 28m

$201

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 8/25

9:40 am-6:57 pm

1 stop8h 17m

Boston Logan Intl

Wed 8/26

4:30 pm-9:58 pm

1 stop6h 28m

$201

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/30

6:24 pm-9:59 pm

Nonstop2h 35m

Boston Logan Intl

Sun 10/4

5:45 am-9:38 am

1 stop4h 53m

$204

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/10

Showing 1-10 of 60 resultsSorted by cheapest first
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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 $181). Flying from Illinois to Boston in June is currently the most expensive (average of $314). 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 July 12, 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 10% versus a flight at noon.

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 July 12, 2026.

The most flights from USIL to BOS are scheduled on a Sunday (77 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (57 on average).

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

How far ahead should I book a flight from Illinois to Boston?

To ensure you get the cheapest price possible for a flight from Illinois to Boston, you should look to book at least 57 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 July 11, 2026.

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

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 JetBlue can get you from Illinois to Boston in just under 2h 15m. Your travel time can differ by up to 4h 34m. The distance from Illinois to Boston is about 857 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 JetBlue, which is currently one of the cheapest options available, starting at $58. Southwest flights start at $61 while deals on United Airlines start at $67 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 (95%), ITA Airways (95%), Etihad Airways (93%).

  • What are the cheapest flights from Illinois to Boston?

    The cheapest flight price from Illinois to Boston is $81. On average you can expect to pay $440. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $130.

  • 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 $181). Flying from Illinois to Boston in June is currently the most expensive (average of $314). 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
Waltham
Cambridge
Concord
Brockton
Hampton Beach
Seekonk
Cranston
Warwick
Dedham
Peabody
Randolph
Auburn
Fitchburg
York Beach
Chelsea
Londonderry
Swansea
North Falmouth
Smithfield
Braintree

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Top 5 airlines flying from Illinois to Boston

Discover the top 5 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 July 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$68Average$178FlexibilityNo cancel feeOn-time62%
DeltaCheapest$86Average$235FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$114Average$249FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$127Average$375FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$136Average$397FlexibilityNo cancel feeOn-time71%

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