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$53+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
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Cheap flight deals from Illinois to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) to Boston (BOS). 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 December 22, 2024.

Round-trip from

$119
(Kiwi.com)

One-way from

$53
(Mytrip)
From Illinois to Boston Logan Intl
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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 December 22, 2024.

This FlightHub deal was found by Cheapflights users on 12/20. 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.
Sun 12/227:00 amORD - BOS
1 stop9h 26mMultiple Airlines
Wed 12/2511:10 amBOS - ORD
1 stop11h 17mMultiple Airlines
Deal found 12/20$222
This American Airlines deal was found by Cheapflights users on 12/20. 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 12/275:42 pmORD - BOS
1 stop4h 10mAmerican Airlines
Wed 1/16:45 amBOS - ORD
Nonstop3h 04mAmerican Airlines
Deal found 12/20$228
This Mytrip deal was found by Cheapflights users on 12/21. 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 12/302:20 pmMDW - BOS
1 stop9h 21mFrontier
Sat 1/256:00 amBOS - MDW
1 stop29h 02mFrontier
Deal found 12/21$242
This Southwest deal was found by Cheapflights users on 12/21. 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.
Wed 12/256:25 pmMDW - BOS
Nonstop2h 10mSouthwest
Tue 1/78:10 amBOS - MDW
Nonstop2h 55mSouthwest
Deal found 12/21$253
This Mytrip deal was found by Cheapflights users on 12/21. 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 12/315:33 pmORD - BOS
1 stop6h 02mFrontier
Tue 1/76:00 amBOS - ORD
1 stop8h 34mFrontier
Deal found 12/21$258
This FlightHub deal was found by Cheapflights users on 12/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/245:11 pmORD - BOS
1 stop17h 14mSpirit Airlines
Sat 12/286:27 amBOS - ORD
1 stop13h 52mSpirit Airlines
Deal found 12/21$273
This Delta deal was found by Cheapflights users on 12/21. 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 12/2710:05 amORD - BOS
1 stop8h 06mDelta
Mon 1/68:20 pmBOS - ORD
Nonstop3h 03mDelta
Deal found 12/21$283
This JetBlue Airways deal was found by Cheapflights users on 12/21. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2410:11 amORD - BOS
1 stop8h 04mJetBlue
Sat 1/46:00 amBOS - ORD
Nonstop3h 07mJetBlue
Deal found 12/21$306
This United Airlines deal was found by Cheapflights users on 12/21. 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 12/306:25 pmORD - BOS
Nonstop2h 29mUnited Airlines
Sun 1/55:29 pmBOS - ORD
1 stop6h 31mUnited Airlines
Deal found 12/21$324
This Delta deal was found by Cheapflights users on 12/19. 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 12/265:04 pmMDW - BOS
1 stop5h 55mDelta
Mon 12/305:25 amBOS - MDW
1 stop4h 25mDelta
Deal found 12/19$326
This Southwest deal was found by Cheapflights users on 12/20. 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.
Tue 12/3111:25 amORD - BOS
2 stops10h 00mSouthwest
Fri 1/38:25 amBOS - ORD
1 stop6h 35mSouthwest
Deal found 12/20$348
This FlightHub deal was found by Cheapflights users on 12/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/298:40 pmSTL - BOS
1 stop13h 15mFrontier
Sun 1/126:00 amBOS - STL
1 stop18h 27mFrontier
Deal found 12/21$355

Find flights from Illinois to Boston within your budget

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/10

4:53 pm-12:30 am

1 stop6h 37m

Boston Logan Intl

Tue 1/14

6:00 am-1:34 pm

1 stop8h 34m

$119

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 2/9

4:18 pm-12:27 am

1 stop7h 09m

Boston Logan Intl

Wed 2/12

10:03 am-10:03 pm

1 stop13h 00m

$123

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 1/26

10:58 am-12:27 am

1 stop12h 29m

Boston Logan Intl

Fri 2/7

6:00 am-2:42 pm

1 stop9h 42m

$128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 2/1

12:25 pm-10:00 pm

1 stop8h 35m

Boston Logan Intl

Wed 2/5

6:25 am-4:10 pm

1 stop10h 45m

$144

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 1/11

7:35 am-12:30 am

1 stop15h 55m

Boston Logan Intl

Mon 1/13

3:50 pm-4:14 pm

1 stop25h 24m

$152

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/11

7:00 am-10:15 am

Nonstop2h 15m

Boston Logan Intl

Tue 1/14

6:10 am-8:14 am

Nonstop3h 04m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 1/17

7:00 pm-10:15 pm

Nonstop2h 15m

Boston Logan Intl

Sun 1/19

8:10 am-10:05 am

Nonstop2h 55m

$158

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/11

6:00 am-9:33 am

Nonstop2h 33m

Boston Logan Intl

Mon 1/13

8:45 am-10:45 am

Nonstop3h 00m

$168

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 1/20

7:10 am-10:47 am

Nonstop2h 37m

Boston Logan Intl

Fri 1/24

7:15 am-9:25 am

Nonstop3h 10m

$187

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/3

9:20 am-12:46 pm

Nonstop2h 26m

Boston Logan Intl

Mon 1/6

7:42 pm-11:34 pm

1 stop4h 52m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 60 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.

Travel insights for flights from Illinois to Boston

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

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 December 22, 2024.

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 December 22, 2024.

The most flights from USIL to BOS are scheduled on a Friday (47 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (15 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 December 22, 2024.
Read reviews from past customers who have flown Southwest, American Airlines and Frontier 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
4,804 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.2

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
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.2

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
9,537 reviews
Southwest
8.1
Very good
4,804 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.2

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
8,597 reviews
Southwest
8.1
Very good
4,804 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.2

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
3,265 reviews
Southwest
8.1
Very good
4,804 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.2

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
9,035 reviews
Southwest
8.1
Very good
4,804 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.2

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 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 Frontier, which is currently one of the cheapest options available, starting at $53. Delta flights start at $79 while deals on Southwest 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: Envoy Air (94%), Royal Jordanian (91%), Etihad Airways (90%).

  • 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 $577. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $114.

  • 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.

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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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$96FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$315FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$69Average$116FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$84Average$241FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$138Average$488FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$149Average$455FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$153Average$275FlexibilityNo cancel feeOn-time63%
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