HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Illinois

$69+ 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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 July 29, 2025.

Round-trip from

$137
(Southwest)

One-way from

$69
(Southwest)

Popular in

March

Cheapest in

September

Average price

$227

Good round-trip deal

$159 or less

Good one-way deal

$133 or less
From Boston Logan Intl to Illinois
Search Deals
One-way flight from Boston Logan Intl to Illinois
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($22 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 July 2025
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Illinois.
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Illinois.
Search Deals

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 July 29, 2025.

This Southwest deal was found by Cheapflights users on 7/28. 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 10/175:15 amBOS - MDW
Nonstop2h 40mSouthwest
Sun 10/196:05 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 7/28$137
This United Airlines deal was found by Cheapflights users on 7/27. 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.
Fri 9/126:16 pmBOS - ORD
Nonstop2h 54mUnited Airlines
Wed 9/171:12 pmORD - BOS
Nonstop2h 31mUnited Airlines
Deal found 7/27$137
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/193:37 pmBOS - ORD
1 stop7h 45mSpirit Airlines
Tue 8/2611:36 amORD - BOS
1 stop11h 13mSpirit Airlines
Deal found 7/29$138
This Trip.com deal was found by Cheapflights users on 7/28. 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.
Thu 8/216:00 amBOS - ORD
Nonstop2h 55mJetBlue
Thu 8/214:27 pmORD - BOS
Nonstop2h 33mJetBlue
Deal found 7/28$142
This Southwest deal was found by Cheapflights users on 7/28. 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 9/410:45 amBOS - ORD
1 stop6h 40mSouthwest
Sun 9/71:50 pmORD - BOS
1 stop5h 45mSouthwest
Deal found 7/28$146
This Delta deal was found by Cheapflights users on 7/29. 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 9/47:20 amBOS - ORD
Nonstop2h 55mDelta
Sun 9/77:00 amORD - BOS
Nonstop2h 30mDelta
Deal found 7/29$155
This American Airlines deal was found by Cheapflights users on 7/27. 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 9/412:33 pmBOS - ORD
Nonstop3h 01mAmerican Airlines
Sun 9/77:10 amORD - BOS
Nonstop2h 19mAmerican Airlines
Deal found 7/27$166
This CheapOair deal was found by Cheapflights users on 7/27. 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 8/1910:34 amBOS - ORD
1 stop12h 48mMultiple Airlines
Sat 8/237:46 pmORD - BOS
1 stop11h 49mMultiple Airlines
Deal found 7/27$180
This Frontier deal was found by Cheapflights users on 7/27. 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 8/169:40 amBOS - MDW
1 stop11h 42mFrontier
Sun 8/173:58 pmMDW - BOS
1 stop7h 40mFrontier
Deal found 7/27$208
This Mytrip deal was found by Cheapflights users on 7/29. 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 9/58:59 amBOS - MDW
1 stop8h 44mAllegiant Air
Mon 9/87:50 pmMDW - BOS
1 stop12h 53mAllegiant Air
Deal found 7/29$209
This Mytrip deal was found by Cheapflights users on 7/29. 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 10/176:08 amBOS - RFD
2 stops13h 50mMultiple Airlines
Sun 10/194:45 pmRFD - BOS
1 stop16h 51mMultiple Airlines
Deal found 7/29$246
This Delta deal was found by Cheapflights users on 7/28. 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 8/263:25 pmBOS - MLI
1 stop8h 23mDelta
Wed 9/34:59 pmMLI - BOS
1 stop7h 25mDelta
Deal found 7/28$251

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 July 29, 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 - MDW

BOSMDW

Boston Logan Intl

Fri 10/17

5:15 am-6:55 am

Nonstop2h 40m

Chicago Midway

Sun 10/19

6:05 am-9:20 am

Nonstop2h 15m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/11

9:43 am-11:33 am

Nonstop2h 50m

Chicago O'Hare Intl

Sun 9/14

6:30 am-9:56 am

Nonstop2h 26m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 8/26

10:34 am-10:22 pm

1 stop12h 48m

Chicago O'Hare Intl

Tue 9/2

8:12 pm-11:18 am

1 stop14h 06m

$138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/21

6:00 am-7:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Thu 8/21

4:27 pm-8:00 pm

Nonstop2h 33m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

7:30 am-12:45 pm

1 stop6h 15m

Chicago O'Hare Intl

Sun 9/7

1:50 pm-8:35 pm

1 stop5h 45m

$146

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

7:20 am-9:15 am

Nonstop2h 55m

Chicago O'Hare Intl

Sun 9/7

7:00 am-10:30 am

Nonstop2h 30m

$155

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

12:33 pm-2:34 pm

Nonstop3h 01m

Chicago O'Hare Intl

Sun 9/7

7:10 am-10:29 am

Nonstop2h 19m

$166

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 8/19

10:34 am-10:22 pm

1 stop12h 48m

Chicago O'Hare Intl

Sat 8/23

7:46 pm-8:35 am

1 stop11h 49m

$180

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 8/16

9:40 am-8:22 pm

1 stop11h 42m

Chicago Midway

Sun 8/17

3:58 pm-12:38 am

1 stop7h 40m

$208

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 9/5

8:59 am-4:43 pm

1 stop8h 44m

Chicago Midway

Mon 9/8

7:50 pm-9:43 am

1 stop12h 53m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 $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 July 29, 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 July 29, 2025.

The most flights from BOS to USIL are scheduled on a Monday (68 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 on average).

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 July 29, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from Boston to Illinois to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,238 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,977 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,899 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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 Southwest ($69), Delta ($69), and American Airlines ($70).

  • 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 Avianca (95%), TAP AIR PORTUGAL (95%) or Icelandair (94%) 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 $1,340, our data shows the cheapest flight currently is $68. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay $117 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

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.
Boston to Las Vegas flights
Boston to Los Angeles flights
Boston to Seattle flights
Boston to Orlando flights
Boston to Dallas/Fort Worth flights
Boston to O'Hare Intl flights
Boston to Baltimore flights
Boston to Reagan-National flights
Boston to Fort Lauderdale flights
Hartford to Orlando flights
Boston to San Francisco flights
Boston to Atlanta flights
Boston to Sky Harbor Intl flights
Boston to Dulles Intl flights
Boston to Denver flights
Boston to Miami flights
Boston to Newark flights
Boston to Nashville flights
Boston to LaGuardia flights
Boston to Charlotte flights
Boston to Tampa flights
Boston to Hobby flights
Boston to Charleston flights
Boston to Philadelphia flights
Boston to Honolulu flights
Boston to Portland flights
Boston to George Bush Intcntl flights
Boston to Minneapolis flights
Boston to West Palm Beach flights
Boston to Salt Lake City flights
Boston to John F Kennedy Intl flights
Boston to Austin flights
Boston to Midway flights
Boston to San Diego flights
Boston to Detroit flights
Hartford to O'Hare Intl flights
Boston to Fort Myers flights
Boston to Cleveland flights
Boston to New Orleans flights
Boston to Pittsburgh flights
Albany to Orlando flights
Hartford to Denver flights
Boston to Raleigh flights
Boston to Cincinnati flights
Hartford to Atlanta flights
Boston to Love Field flights
Hartford to Dallas/Fort Worth flights
Boston to Ontario flights
Boston to Indianapolis flights
Hartford to Tampa flights

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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$37Average$138FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$74Average$202FlexibilityNo cancel feeOn-time62%
DeltaCheapest$94Average$358FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$97Average$455FlexibilityNo cancel feeOn-time69%
FrontierCheapest$100Average$120FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$125Average$233FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$136Average$413FlexibilityNo cancel feeOn-time71%

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.