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$68+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
jul. 6 — jul. 131
dom. 7/6
dom. 7/13
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 julio 1, 2025.

Round-trip from

$132
(Priceline)

One-way from

$68
(FlightHub)

Popular in

April

Cheapest in

August

Average price

$225

Good round-trip deal

$137 or less

Good one-way deal

$68 or less
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. 9% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 1, 2025.

This Priceline deal was found by Cheapflights users on 6/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/911:45 amORD - BOS
1 stop11h 10mMultiple Airlines
sáb. 9/138:38 amBOS - ORD
1 stop9h 11mMultiple Airlines
Deal found 6/29$132
This Priceline deal was found by Cheapflights users on 6/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/212:20 pmORD - BOS
1 stop11h 19mFrontier
jue. 8/76:00 amBOS - ORD
1 stop8h 56mFrontier
Deal found 6/29$135
This JetBlue deal was found by Cheapflights users on 6/30. 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.
vie. 7/118:40 amORD - BOS
Nonstop2h 24mJetBlue
mié. 7/166:00 amBOS - ORD
Nonstop2h 55mJetBlue
Deal found 6/30$137
This Southwest deal was found by Cheapflights users on 6/30. 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.
sáb. 8/163:55 pmMDW - BOS
Nonstop2h 20mSouthwest
lun. 8/185:15 amBOS - MDW
Nonstop2h 30mSouthwest
Deal found 6/30$137
This American Airlines deal was found by Cheapflights users on 6/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/108:30 pmORD - BOS
Nonstop2h 44mAmerican Airlines
dom. 7/135:00 amBOS - ORD
Nonstop2h 58mAmerican Airlines
Deal found 6/29$139
This FlightHub deal was found by Cheapflights users on 6/29. 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.
mar. 7/155:05 amORD - BOS
1 stop13h 29mSpirit Airlines
mar. 7/228:39 pmBOS - ORD
1 stop13h 16mSpirit Airlines
Deal found 6/29$140
This CheapOair deal was found by Cheapflights users on 6/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/196:21 amMDW - BOS
1 stop24h 50mFrontier
lun. 9/2210:53 amBOS - MDW
1 stop6h 05mFrontier
Deal found 6/29$140
This United Airlines deal was found by Cheapflights users on 6/30. 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.
mar. 7/1511:05 amORD - BOS
Nonstop2h 37mUnited Airlines
mar. 7/157:04 pmBOS - ORD
1 stop5h 37mUnited Airlines
Deal found 6/30$143
This Delta deal was found by Cheapflights users on 6/30. 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.
mié. 7/237:00 amORD - BOS
Nonstop2h 31mDelta
mié. 7/234:05 pmBOS - ORD
Nonstop3h 06mDelta
Deal found 6/30$155
This Southwest deal was found by Cheapflights users on 6/30. 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.
vie. 8/222:55 pmORD - BOS
1 stop6h 40mSouthwest
mar. 8/265:40 amBOS - ORD
1 stop7h 10mSouthwest
Deal found 6/30$157
This Mytrip deal was found by Cheapflights users on 6/30. 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.
dom. 8/35:33 pmPIA - BOS
1 stop16h 19mMultiple Airlines
jue. 8/78:48 pmBOS - PIA
2 stops18h 25mMultiple Airlines
Deal found 6/30$240
This Delta deal was found by Cheapflights users on 6/30. 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.
mié. 8/134:59 pmMLI - BOS
1 stop7h 21mDelta
mié. 8/205:25 pmBOS - MLI
1 stop6h 23mDelta
Deal found 6/30$251

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 julio 1, 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

mar. 9/9

11:45 am-11:55 pm

1 stop11h 10m

Boston Logan Intl

sáb. 9/13

8:38 am-4:49 pm

1 stop9h 11m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 8/2

12:20 pm-12:39 am

1 stop11h 19m

Boston Logan Intl

jue. 8/7

6:00 am-1:56 pm

1 stop8h 56m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 7/11

8:40 am-12:04 pm

Nonstop2h 24m

Boston Logan Intl

mié. 7/16

6:00 am-7:55 am

Nonstop2h 55m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

sáb. 8/16

3:55 pm-7:15 pm

Nonstop2h 20m

Boston Logan Intl

lun. 8/18

5:15 am-6:45 am

Nonstop2h 30m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 7/29

5:05 am-7:34 pm

1 stop13h 29m

Boston Logan Intl

mar. 7/29

8:39 pm-8:55 am

1 stop13h 16m

$138

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

vie. 9/19

6:21 am-8:11 am

1 stop24h 50m

Boston Logan Intl

lun. 9/22

10:53 am-3:58 pm

1 stop6h 05m

$140

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 7/15

11:05 am-2:42 pm

Nonstop2h 37m

Boston Logan Intl

mar. 7/15

7:04 pm-11:41 pm

1 stop5h 37m

$143

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 8/22

2:55 pm-10:35 pm

1 stop6h 40m

Boston Logan Intl

mar. 8/26

5:40 am-11:50 am

1 stop7h 10m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 8/29

8:25 pm-11:59 pm

Nonstop2h 34m

Boston Logan Intl

mar. 9/2

8:35 am-10:30 am

Nonstop2h 55m

$165

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 8/30

2:10 pm-5:54 pm

Nonstop2h 44m

Boston Logan Intl

dom. 8/31

7:20 am-9:15 am

Nonstop2h 55m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

Showing 1-10 of 58 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 June is currently the most expensive (average of $306). 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 julio 1, 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 julio 1, 2025.

The most flights from USIL to BOS are scheduled on a Monday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

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 julio 1, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Illinois to Boston to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,273 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,273 reviews
Southwest
8.0
Very good
4,273 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,273 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,858 reviews
Southwest
8.0
Very good
4,273 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,919 reviews
Southwest
8.0
Very good
4,273 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,273 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $68. JetBlue flights start at $69 while deals on Southwest start at $69 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: Etihad Airways (91%), Scandinavian Airlines (90%), Royal Jordanian (84%).

  • What are the cheapest flights from Illinois to Boston?

    The cheapest flight price from Illinois to Boston is $68. On average you can expect to pay $853. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $125.

  • 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 June is currently the most expensive (average of $306). 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
Cambridge
Medford
Watertown
Warwick
Seabrook
Waltham
Framingham
Cranston
Randolph
Chestnut Hill
Chelsea
Brockton
York Beach
Saco
Burlington
West Yarmouth
Smithfield
Swansea
Lincoln
Quincy

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Alternative routes for Illinois to Boston

See prices for flight routes from nearby airports that may be better suited for you.
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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 julio 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$36Average$95FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$78Average$194FlexibilityNo cancel feeOn-time62%
DeltaCheapest$90Average$222FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$125Average$464FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$130Average$385FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$153Average$276FlexibilityNo cancel feeOn-time63%

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