Illinois

$64+ Cheap flights from Boston (BOS) to Illinois

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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Apr 16 — Apr 231
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Cheap flight deals from Boston to Illinois

Keep the following information in mind while searching for Boston to Illinois flight deals. Data was last updated April 11, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$123
(United Airlines)

One-way from

$64
(United Airlines)

Popular in

May

Cheapest in

September

Average price

$268

Good round-trip deal

$203 or less

Good one-way deal

$115 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
From Boston Logan Intl to Illinois
One-way flight from Boston Logan Intl to Illinois
Highest demand for flights based on searches. 9% potential increase in price ($26 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Average for round-trip flights in April 2025
Price to beat on a round-trip flight from Boston Logan Intl to Illinois.
Price to beat on a one-way flight from Boston Logan Intl to Illinois.

Find flight deals from Boston to Illinois

Cheapest flights from Boston to Illinois
Explore the most affordable flight options available from Boston to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 11, 2025.

This United Airlines deal was found by Cheapflights users on 4/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/16:59 pmBOS - ORD
1 stop5h 38mUnited Airlines
Thu 7/316:00 amORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 4/10$123
This Southwest deal was found by Cheapflights users on 4/10. 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 5/15:45 amBOS - MDW
Nonstop2h 35mSouthwest
Mon 5/52:40 pmMDW - BOS
1 stop7h 35mSouthwest
Deal found 4/10$127
This JetBlue deal was found by Cheapflights users on 4/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/74:30 pmBOS - ORD
Nonstop3h 06mJetBlue
Sat 5/106:10 amORD - BOS
1 stop4h 32mJetBlue
Deal found 4/10$127
This Cheapflightsfares deal was found by Cheapflights users on 4/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/62:12 pmBOS - ORD
1 stop11h 08mSpirit Airlines
Sat 5/1012:41 pmORD - BOS
1 stop9h 48mSpirit Airlines
Deal found 4/10$131
This Southwest deal was found by Cheapflights users on 4/10. 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.
Sat 6/76:45 amBOS - ORD
1 stop9h 15mSouthwest
Wed 6/114:00 pmORD - BOS
1 stop6h 55mSouthwest
Deal found 4/10$136
This American Airlines deal was found by Cheapflights users on 4/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/316:35 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Thu 6/56:45 amORD - BOS
Nonstop2h 23mAmerican Airlines
Deal found 4/10$149
This Delta deal was found by Cheapflights users on 4/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/104:05 pmBOS - ORD
Nonstop2h 59mDelta
Fri 6/136:59 pmORD - BOS
Nonstop2h 46mDelta
Deal found 4/10$157
This Trip.com deal was found by Cheapflights users on 4/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/133:49 pmBOS - ORD
1 stop8h 15mMultiple Airlines
Fri 5/164:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Deal found 4/10$159
This CheapOair deal was found by Cheapflights users on 4/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/156:00 amBOS - MDW
1 stop11h 08mFrontier
Wed 4/163:00 pmMDW - BOS
1 stop19h 50mFrontier
Deal found 4/10$180
This Frontier deal was found by Cheapflights users on 4/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/125:45 amBOS - ORD
1 stop9h 13mFrontier
Tue 4/159:32 amORD - BOS
1 stop13h 53mFrontier
Deal found 4/10$198
This Mytrip deal was found by Cheapflights users on 4/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1111:42 amBOS - RFD
1 stop23h 31mMultiple Airlines
Sun 7/139:21 amRFD - BOS
1 stop24h 18mMultiple Airlines
Deal found 4/10$233
This Mytrip deal was found by Cheapflights users on 4/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2211:31 amBOS - MDW
1 stop25h 54mAllegiant Air
Mon 5/262:54 pmMDW - BOS
1 stop17h 20mAllegiant Air
Deal found 4/10$244

Cheapflights Fare Finder

Customize your flight search to find flights from Boston to Illinois 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 April 11, 2025.
Use the filters below to find and compare flights from Boston to Illinois that are best for you.

Fly from

Boston

Fly to

Illinois

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/1

6:59 pm-11:37 pm

1 stop5h 38m

Chicago O'Hare Intl

Thu 7/31

6:00 am-9:26 am

Nonstop2h 26m

$123

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 5/1

5:45 am-7:20 am

Nonstop2h 35m

Chicago Midway

Mon 5/5

2:40 pm-11:15 pm

1 stop7h 35m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 5/7

4:30 pm-6:36 pm

Nonstop3h 06m

Chicago O'Hare Intl

Sat 5/10

6:10 am-11:42 am

1 stop4h 32m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 5/6

2:12 pm-12:20 am

1 stop11h 08m

Chicago O'Hare Intl

Sat 5/10

12:41 pm-11:29 pm

1 stop9h 48m

$131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 6/7

6:45 am-3:00 pm

1 stop9h 15m

Chicago O'Hare Intl

Wed 6/11

4:00 pm-11:55 pm

1 stop6h 55m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/31

6:35 am-8:31 am

Nonstop2h 56m

Chicago O'Hare Intl

Thu 6/5

6:45 am-10:08 am

Nonstop2h 23m

$149

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 6/10

4:05 pm-6:04 pm

Nonstop2h 59m

Chicago O'Hare Intl

Fri 6/13

6:59 pm-10:45 pm

Nonstop2h 46m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 5/13

3:49 pm-11:04 pm

1 stop8h 15m

Chicago O'Hare Intl

Fri 5/16

4:15 pm-12:44 am

1 stop7h 29m

$159

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 5/7

8:00 am-12:24 pm

1 stop29h 24m

Chicago Midway

Fri 5/9

1:19 pm-12:44 am

1 stop10h 25m

$190

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 4/14

10:25 am-12:23 am

1 stop14h 58m

Chicago O'Hare Intl

Tue 4/15

9:44 am-12:47 am

1 stop14h 03m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/10

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

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

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

Currently, August is the cheapest month in which you can book a flight from Boston to Illinois (average of $245). Flying from Boston to Illinois in March is currently the most expensive (average of $321). 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 BOS to IL?

Find hourly flight availability from Boston to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 11, 2025.

When flying from Boston to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Boston to Illinois

Explore weekly flight availability from Boston to Illinois. 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 April 11, 2025.

The most flights from BOS to USIL are scheduled on a Friday (60 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated April 11, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Boston to Illinois by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
8.0
Very good

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Related info for your journey

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

    If you book a flight to Illinois from Boston, you will be flying from Logan Intl, which is the city’s only airport. Boston Logan Intl (BOS) is located 2.6 mi from the center of Boston.

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

    The cheapest airlines for a one-way flight from Boston to Illinois are United Airlines ($64), Southwest ($68), and JetBlue ($69).

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

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

    No one likes to see their flight delayed. When booking a flight from Boston to Illinois consider choosing LATAM Airlines (100%), KLM (94%) or WestJet (91%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Boston to Illinois?

    While on average a flight from Boston to Illinois is generally $596, our data shows the cheapest flight currently is $57. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay $110 for that flight.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Boston to Illinois (average of $245). Flying from Boston to Illinois in March is currently the most expensive (average of $321). 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

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Alternative routes for Boston to Illinois

See prices for flight routes from nearby airports that may be better suited for you.

Top 7 airlines flying from Boston to Illinois

Discover the top 7 airlines that operate flights from Boston to Illinois. 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 April 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$104FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$84Average$227FlexibilityNo cancel feeOn-time62%
DeltaCheapest$94Average$325FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$97Average$501FlexibilityNo cancel feeOn-time69%
FrontierCheapest$99Average$151FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$140Average$475FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$143Average$305FlexibilityNo cancel feeOn-time63%

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