Illinois

$79+ 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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Mar 30 — Apr 61
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Boston to Illinois 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 Boston to Illinois

Keep the following information in mind while searching for Boston to Illinois flight deals. Data was last updated March 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$152
(JetBlue)

One-way from

$79
(United Airlines)

Popular in

May

Cheapest in

September

Average price

$277

Good round-trip deal

$240 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. 11% potential increase in price ($31 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Average for round-trip flights in March 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 March 25, 2025.

This United Airlines deal was found by Cheapflights users on 3/24. 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 8/257:30 pmBOS - ORD
1 stop5h 12mUnited Airlines
Fri 8/299:15 pmORD - BOS
Nonstop2h 30mUnited Airlines
Deal found 3/24$150
This JetBlue deal was found by Cheapflights users on 3/24. 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 8/66:00 amBOS - ORD
Nonstop2h 55mJetBlue
Mon 8/116:00 amORD - BOS
1 stop4h 51mJetBlue
Deal found 3/24$152
This Cheapflightsfares deal was found by Cheapflights users on 3/24. 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.
Fri 4/258:35 pmBOS - ORD
1 stop13h 49mSpirit Airlines
Wed 4/307:47 pmORD - BOS
1 stop13h 35mSpirit Airlines
Deal found 3/24$155
This Southwest deal was found by Cheapflights users on 3/24. 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 5/24:40 pmBOS - MDW
Nonstop2h 40mSouthwest
Sun 5/46:50 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 3/24$157
This American Airlines deal was found by Cheapflights users on 3/23. 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.
Fri 4/45:00 amBOS - ORD
Nonstop2h 55mAmerican Airlines
Wed 4/98:05 amORD - BOS
Nonstop2h 25mAmerican Airlines
Deal found 3/23$158
This Southwest deal was found by Cheapflights users on 3/23. 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.
Sun 4/135:45 amBOS - ORD
1 stop7h 05mSouthwest
Wed 4/161:50 pmORD - BOS
1 stop4h 20mSouthwest
Deal found 3/23$176
This Delta deal was found by Cheapflights users on 3/24. 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.
Thu 5/15:10 pmBOS - ORD
Nonstop3h 04mDelta
Sun 5/47:00 amORD - BOS
Nonstop2h 26mDelta
Deal found 3/24$197
This CheapOair deal was found by Cheapflights users on 3/24. 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 5/155:04 pmBOS - ORD
1 stop8h 20mMultiple Airlines
Sun 5/184:15 pmORD - BOS
1 stop7h 50mMultiple Airlines
Deal found 3/24$221
This Frontier deal was found by Cheapflights users on 3/25. 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.
Fri 5/96:00 amBOS - MDW
1 stop7h 24mFrontier
Fri 5/161:19 pmMDW - BOS
1 stop10h 25mFrontier
Deal found 3/25$239
This Mytrip deal was found by Cheapflights users on 3/24. 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 5/156:00 amBOS - PIA
2 stops28h 19mMultiple Airlines
Mon 5/194:14 pmPIA - BOS
2 stops15h 55mMultiple Airlines
Deal found 3/24$274
This Mytrip deal was found by Cheapflights users on 3/24. 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 6/127:00 amBOS - RFD
2 stops9h 16mMultiple Airlines
Sun 6/154:06 pmRFD - BOS
1 stop18h 03mMultiple Airlines
Deal found 3/24$277
This Cheapflightsfares deal was found by Cheapflights users on 3/24. 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 5/2211:41 amBOS - ORD
1 stop6h 40mSun Country Air
Mon 5/269:05 pmORD - BOS
1 stop13h 50mSun Country Air
Deal found 3/24$280

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 March 25, 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

Wed 4/9

5:15 pm-7:27 pm

Nonstop3h 12m

Chicago O'Hare Intl

Fri 4/11

8:29 pm-11:58 pm

Nonstop2h 29m

$154

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 4/25

8:35 pm-9:24 am

1 stop13h 49m

Chicago O'Hare Intl

Wed 4/30

7:47 pm-10:22 am

1 stop13h 35m

$155

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 5/2

4:40 pm-6:20 pm

Nonstop2h 40m

Chicago Midway

Sun 5/4

6:50 am-10:05 am

Nonstop2h 15m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 4/4

5:00 am-6:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Tue 4/8

9:50 am-1:20 pm

Nonstop2h 30m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 6/12

7:45 am-9:43 am

Nonstop2h 58m

Chicago O'Hare Intl

Sun 6/15

6:30 am-9:56 am

Nonstop2h 26m

$161

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 4/13

5:45 am-11:50 am

1 stop7h 05m

Chicago O'Hare Intl

Wed 4/16

1:50 pm-7:10 pm

1 stop4h 20m

$176

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 5/1

7:30 am-9:30 am

Nonstop3h 00m

Chicago O'Hare Intl

Sun 5/4

7:00 am-10:26 am

Nonstop2h 26m

$197

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 5/15

5:04 pm-12:24 am

1 stop8h 20m

Chicago O'Hare Intl

Sun 5/18

4:15 pm-1:05 am

1 stop7h 50m

$221

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 5/9

6:00 am-12:24 pm

1 stop7h 24m

Chicago Midway

Fri 5/16

1:19 pm-12:44 am

1 stop10h 25m

$239

BostonPeoria

BOS - PIA

BOSPIA

Boston Logan Intl

Thu 5/15

6:00 am-9:19 am

2 stops28h 19m

Greater Peoria

Mon 5/19

4:14 pm-9:09 am

2 stops15h 55m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

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

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 $323). 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 March 25, 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 March 25, 2025.

The most flights from BOS to USIL are scheduled on a Tuesday (51 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 March 25, 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

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
8.0
Very good

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 ($79), Spirit Airlines ($83), and JetBlue ($99).

  • 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 WestJet (96%), Avianca (89%) or Virgin Atlantic (86%) 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 $888, 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 $97 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 $323). 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

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 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 March 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$105FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$83Average$235FlexibilityNo cancel feeOn-time62%
DeltaCheapest$97Average$336FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$98Average$147FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$142Average$481FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$511FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$153Average$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.