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$77+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Apr 1 — Apr 81
Tue 4/1
Tue 4/8
1 adult, Economy
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Cheap flight deals from Illinois to Boston

Keep the following information in mind while searching for Illinois to Boston flight deals. Data was last updated March 27, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$131
(Kiwi.com)

One-way from

$77
(FlightHub)

Popular in

April

Cheapest in

September

Average price

$278

Good round-trip deal

$201 or less

Good one-way deal

$88 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
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From Illinois to Boston Logan Intl
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One-way flight from Illinois to Boston Logan Intl
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Highest demand for flights based on searches. 15% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Illinois to Boston Logan Intl.
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Price to beat on a one-way flight from Illinois to Boston Logan Intl.
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Find 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 March 27, 2025.

This Kiwi.com deal was found by Cheapflights users on 3/26. 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.
Wed 5/1412:41 pmORD - BOS
1 stop9h 48mSpirit Airlines
Mon 5/1910:30 amBOS - ORD
1 stop6h 55mSpirit Airlines
Deal found 3/26$131
This JetBlue deal was found by Cheapflights users on 3/26. 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.
Fri 6/66:30 pmORD - BOS
Nonstop2h 29mJetBlue
Sun 6/86:00 amBOS - ORD
Nonstop3h 01mJetBlue
Deal found 3/26$132
This Southwest deal was found by Cheapflights users on 3/26. 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 4/94:00 pmORD - BOS
2 stops14h 50mSouthwest
Mon 4/145:00 amBOS - ORD
1 stop8h 45mSouthwest
Deal found 3/26$133
This Delta deal was found by Cheapflights users on 3/26. 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 5/92:15 pmORD - BOS
Nonstop2h 32mDelta
Sat 5/107:15 amBOS - ORD
Nonstop2h 54mDelta
Deal found 3/26$137
This American Airlines deal was found by Cheapflights users on 3/26. 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.
Wed 4/308:05 amORD - BOS
Nonstop2h 25mAmerican Airlines
Mon 5/58:51 pmBOS - ORD
Nonstop3h 01mAmerican Airlines
Deal found 3/26$138
This United Airlines deal was found by Cheapflights users on 3/26. 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 6/59:30 pmORD - BOS
Nonstop2h 29mUnited Airlines
Sun 6/86:00 amBOS - ORD
Nonstop2h 58mUnited Airlines
Deal found 3/26$150
This Southwest deal was found by Cheapflights users on 3/26. 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 4/105:30 amMDW - BOS
Nonstop2h 15mSouthwest
Mon 4/144:40 pmBOS - MDW
Nonstop2h 40mSouthwest
Deal found 3/26$157
This Mytrip deal was found by Cheapflights users on 3/26. 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 5/29:07 pmPIA - BOS
1 stop20h 36mMultiple Airlines
Sun 5/47:48 pmBOS - PIA
1 stop19h 30mMultiple Airlines
Deal found 3/26$177
This Booking.com deal was found by Cheapflights users on 3/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/247:15 pmORD - BOS
1 stop14h 20mMultiple Airlines
Tue 4/292:12 pmBOS - ORD
1 stop11h 08mMultiple Airlines
Deal found 3/26$179
This Mytrip deal was found by Cheapflights users on 3/26. 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 5/308:04 pmMDW - BOS
1 stop12h 08mAllegiant Air
Sun 6/111:31 amBOS - MDW
1 stop27h 55mAllegiant Air
Deal found 3/26$235
This Frontier deal was found by Cheapflights users on 3/26. 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 5/91:19 pmMDW - BOS
1 stop10h 25mFrontier
Sun 5/1810:14 amBOS - MDW
1 stop13h 26mFrontier
Deal found 3/26$238
This CheapOair deal was found by Cheapflights users on 3/26. 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.
Fri 4/49:54 amORD - BOS
1 stop13h 53mFrontier
Sat 4/59:06 amBOS - ORD
1 stop15h 40mFrontier
Deal found 3/26$240

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 March 27, 2025.
Use the filters below to find and compare flights from Illinois to Boston that are best for you.

Fly from

Illinois

Fly to

Boston

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/14

12:41 pm-11:29 pm

1 stop9h 48m

Boston Logan Intl

Mon 5/19

10:30 am-4:25 pm

1 stop6h 55m

$131

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 6/6

6:30 pm-9:59 pm

Nonstop2h 29m

Boston Logan Intl

Sun 6/8

6:00 am-8:01 am

Nonstop3h 01m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 4/9

4:00 pm-7:50 am

2 stops14h 50m

Boston Logan Intl

Mon 4/14

5:00 am-12:45 pm

1 stop8h 45m

$133

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 4/30

8:05 am-11:30 am

Nonstop2h 25m

Boston Logan Intl

Mon 5/5

8:51 pm-10:52 pm

Nonstop3h 01m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/10

10:55 am-2:18 pm

Nonstop2h 23m

Boston Logan Intl

Mon 4/14

8:10 pm-10:06 pm

Nonstop2h 56m

$147

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 6/5

9:30 pm-12:59 am

Nonstop2h 29m

Boston Logan Intl

Sun 6/8

6:00 am-7:58 am

Nonstop2h 58m

$150

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 4/10

5:30 am-8:45 am

Nonstop2h 15m

Boston Logan Intl

Mon 4/14

4:40 pm-6:20 pm

Nonstop2h 40m

$157

PeoriaBoston

PIA - BOS

PIABOS

Greater Peoria

Fri 5/2

9:07 pm-6:43 pm

1 stop20h 36m

Boston Logan Intl

Sun 5/4

7:48 pm-2:18 pm

1 stop19h 30m

$177

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/24

7:15 pm-10:35 am

1 stop14h 20m

Boston Logan Intl

Tue 4/29

2:12 pm-12:20 am

1 stop11h 08m

$179

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 5/30

8:04 pm-9:12 am

1 stop12h 08m

Boston Logan Intl

Sun 6/1

11:31 am-2:26 pm

1 stop27h 55m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 57 results
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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, January is the cheapest month in which you can book a flight from Illinois to Boston (average of $218). Flying from Illinois to Boston in July is currently the most expensive (average of $311). 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 March 27, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Boston as you normally would.

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 March 27, 2025.

The most flights from USIL to BOS are scheduled on a Monday (53 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Boston by month

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

In terms of precipitation, rainfall in Boston ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Boston when rainfall is around 3.1 in.

Temperature in Boston by month

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

If weather is an important factor for your trip to Boston, 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 30.2 F).

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated March 27, 2025.
Read reviews from past customers who have flown Southwest, Alaska Airlines and Delta from Illinois to Boston. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,273 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Alaska Airlines
8.0
Very good
9,792 reviews
Southwest
8.1
Very good
4,273 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,895 reviews
Southwest
8.1
Very good
4,273 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,603 reviews
Southwest
8.1
Very good
4,273 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,923 reviews
Southwest
8.1
Very good
4,273 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $77. United Airlines flights start at $78 while deals on JetBlue start at $79 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: Air France (100%), WestJet (95%), LATAM Airlines (93%).

  • What are the cheapest flights from Illinois to Boston?

    The cheapest flight price from Illinois to Boston is $78. On average you can expect to pay $408. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $97.

  • 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, January is the cheapest month in which you can book a flight from Illinois to Boston (average of $218). Flying from Illinois to Boston in July is currently the most expensive (average of $311). 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 Illinois?

Book flights to Illinois if you plan to visit one of these locations
Warwick
Marlborough
Waltham
Cambridge
Framingham
Chestnut Hill
Seekonk
Randolph
Brockton
Lowell
West Yarmouth
Woburn
Somerville
Saco
Burlington
Smithfield
Salem
Chelsea
Seabrook
Brookline

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Top 7 airlines flying from Illinois to Boston

Discover the top 7 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 March 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$96FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$302FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$69Average$115FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$83Average$235FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$144Average$484FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$157Average$436FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$286FlexibilityNo cancel feeOn-time63%
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