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$60+ 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Boston to Illinois

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Illinois (USIL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$147
(Mytrip)

One-way from

$60
(Trip.com)

Good round-trip deal

$224 or less

Good one-way deal

$133 or less
From Boston Logan Intl to Illinois
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One-way flight from Boston Logan Intl to Illinois
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Price to beat on a round-trip flight from Boston Logan Intl to Illinois.
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Price to beat on a one-way flight from Boston Logan Intl to Illinois.
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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 January 21, 2025.

This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1010:21 pmBOS - ORD
2 stops16h 18mSpirit Airlines
Wed 3/126:45 amORD - BOS
1 stop8h 25mSpirit Airlines
Deal found 1/21$147
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.
Fri 2/76:00 amBOS - ORD
1 stop15h 57mFrontier
Mon 2/104:41 pmORD - BOS
1 stop6h 58mFrontier
Deal found 1/21$148
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.
Mon 3/105:10 amBOS - ORD
1 stop12h 21mMultiple Airlines
Mon 3/176:45 amORD - BOS
1 stop8h 25mMultiple Airlines
Deal found 1/21$149
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/110:24 amBOS - MDW
1 stop13h 16mFrontier
Sun 5/44:00 pmMDW - BOS
1 stop16h 34mFrontier
Deal found 1/21$150
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.
Thu 2/136:50 amBOS - MDW
Nonstop2h 55mSouthwest
Tue 2/187:00 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 1/21$157
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/218:20 pmBOS - ORD
Nonstop2h 59mDelta
Wed 2/267:10 amORD - BOS
Nonstop2h 33mDelta
Deal found 1/21$157
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.
Mon 2/2410:00 amBOS - ORD
Nonstop3h 00mJetBlue
Sat 3/112:38 pmORD - BOS
Nonstop2h 20mJetBlue
Deal found 1/21$167
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/96:00 amBOS - STL
1 stop18h 46mFrontier
Sun 4/134:57 pmSTL - BOS
1 stop6h 50mFrontier
Deal found 1/21$170
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.
Mon 3/104:17 pmBOS - ORD
1 stop6h 43mUnited Airlines
Wed 3/1211:15 amORD - BOS
Nonstop2h 19mUnited Airlines
Deal found 1/21$183
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/135:20 amBOS - ORD
Nonstop3h 01mAmerican Airlines
Sun 2/168:05 amORD - BOS
Nonstop2h 14mAmerican Airlines
Deal found 1/21$189
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/286:00 amBOS - STL
1 stop9h 43mSpirit Airlines
Thu 1/304:28 pmSTL - BOS
1 stop17h 08mSpirit Airlines
Deal found 1/21$225
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.
Thu 2/135:45 amBOS - ORD
1 stop9h 15mSouthwest
Tue 2/1811:25 amORD - BOS
1 stop5h 20mSouthwest
Deal found 1/21$227

Find flights from Boston to Illinois within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 3/10

10:21 pm-1:39 pm

2 stops16h 18m

Chicago O'Hare Intl

Wed 3/12

5:10 am-4:32 pm

1 stop10h 22m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 3/20

5:10 am-10:50 am

1 stop6h 40m

Chicago O'Hare Intl

Mon 3/24

5:37 pm-12:44 am

1 stop6h 07m

$148

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 2/21

11:11 am-9:25 pm

1 stop11h 14m

Chicago Midway

Thu 2/27

4:04 pm-10:21 am

1 stop17h 17m

$150

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/29

6:00 am-12:45 pm

1 stop7h 45m

Chicago O'Hare Intl

Sat 2/1

12:25 pm-10:00 pm

1 stop8h 35m

$151

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 2/13

6:50 am-8:45 am

Nonstop2h 55m

Chicago Midway

Sun 2/16

8:20 pm-11:35 pm

Nonstop2h 15m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 2/12

3:52 pm-5:55 pm

Nonstop3h 03m

Chicago O'Hare Intl

Sat 2/15

12:45 pm-4:08 pm

Nonstop2h 23m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 2/24

8:20 pm-10:19 pm

Nonstop2h 59m

Chicago O'Hare Intl

Mon 3/3

7:10 am-10:43 am

Nonstop2h 33m

$167

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 2/6

2:52 pm-4:52 pm

Nonstop3h 00m

Chicago O'Hare Intl

Mon 2/10

8:05 am-11:26 am

Nonstop2h 21m

$168

BostonSt. Louis

BOS - STL

BOSSTL

Boston Logan Intl

Wed 4/9

6:00 am-11:46 pm

1 stop18h 46m

Lambert-St Louis

Sun 4/13

4:57 pm-12:47 am

1 stop6h 50m

$170

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/31

12:12 pm-2:08 pm

Nonstop2h 56m

Chicago O'Hare Intl

Mon 2/3

1:15 pm-7:00 pm

1 stop4h 45m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 58 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.

Travel insights for flights from Boston to Illinois

Get recent, data-driven insights about flights from Boston to Illinois including ideal travel times, pricing trends, and more.

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 $320). 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 January 21, 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 January 21, 2025.

The most flights from BOS to USIL are scheduled on a Monday (49 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 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 January 21, 2025.
Get a feel of what it's like to fly with American Airlines, Frontier and Spirit Airlines 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.
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,706 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,201 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,985 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier ($60), Spirit Airlines ($70), and Southwest ($79).

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

    The most popular flight routes from Boston to Illinois are Boston Logan Intl - Chicago O'Hare Intl, Boston Logan Intl - Chicago Midway and Boston Logan Intl - Lambert-St Louis.

  • 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 Air France (100%), Spirit Airlines (100%) or Cathay Pacific (96%) 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 $892, our data shows the cheapest flight currently is $78. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay $113 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 $320). 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.

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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.
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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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$106FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$81Average$239FlexibilityNo cancel feeOn-time62%
DeltaCheapest$93Average$344FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$98Average$144FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$139Average$487FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$510FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$149Average$239FlexibilityNo cancel feeOn-time63%
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