$61+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Feb 26 — Mar 51
1 adult, Economy
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Cheapest flights from Boston to IllinoisExplore 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 January 27, 2026.
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 January 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Sun 3/16:00 am
BOS
- ORD
1 stop29h 51m
Frontier
Tue 3/311:56 am
ORD
- BOS
1 stop12h 17m
Frontier
Deal found 1/26![Frontier logo]()
$132
This Super.com deal was found by Cheapflights users on 1/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/53:35 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Sat 2/77:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Deal found 1/26![JetBlue logo]()
$133
This Southwest deal was found by Cheapflights users on 1/26. 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 2/265:00 am
BOS
- MDW
Nonstop2h 55m
Southwest
Sun 3/16:05 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 1/26![Southwest logo]()
$135
This United Airlines deal was found by Cheapflights users on 1/27. 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 1/304:16 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 2/17:30 am
ORD
- BOS
Nonstop2h 22m
United Airlines
Deal found 1/27![United Airlines logo]()
$135
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Mon 2/26:10 am
BOS
- ORD
Nonstop3h 10m
American Airlines
Tue 2/35:25 pm
ORD
- BOS
Nonstop2h 20m
American Airlines
Deal found 1/26![American Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
BOS
- ORD
1 stop11h 52m
Multiple Airlines
Tue 3/37:23 pm
ORD
- BOS
1 stop20h 22m
Multiple Airlines
Deal found 1/25![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:00 am
BOS
- ORD
1 stop17h 39m
Multiple Airlines
Thu 3/59:18 am
ORD
- BOS
1 stop13h 41m
Multiple Airlines
Deal found 1/25![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:00 am
BOS
- ORD
1 stop29h 51m
Multiple Airlines
Thu 3/59:18 am
ORD
- BOS
1 stop13h 41m
Multiple Airlines
Deal found 1/25![Multiple Airlines logo]()
$139
This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/13:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Thu 2/57:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Deal found 1/25![JetBlue logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/106:00 am
BOS
- MDW
1 stop14h 07m
Frontier
Thu 2/126:25 am
MDW
- BOS
1 stop17h 48m
Frontier
Deal found 1/25![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Thu 2/266:00 am
BOS
- ORD
1 stop17h 39m
Frontier
Wed 3/411:51 am
ORD
- BOS
1 stop12h 22m
Frontier
Deal found 1/26![Frontier logo]()
$141
This Travelocity deal was found by Cheapflights users on 1/26. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:00 am
BOS
- ORD
Nonstop3h 10m
Multiple Airlines
Mon 3/24:42 pm
ORD
- BOS
1 stop7h 31m
Multiple Airlines
Deal found 1/26![Multiple Airlines logo]()
$142
Find flight deals from Boston to Illinois
Keep the following information in mind while searching for Boston to Illinois flight deals. Data was last updated January 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $132 (Kiwi.com) |
One-way from | $61 (Trip.com) |
Popular in | April |
Cheapest in | September |
Average price | $206 |
Good round-trip deal | $209 or less |
Good one-way deal | $120 or less |
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 January 27, 2026.
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
Sun 2/22
7:45 am-9:50 am
Nonstop3h 05m
Chicago O'Hare Intl
Sun 3/1
7:30 am-10:49 am
Nonstop2h 19m
$132
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 3/21
6:30 am-8:20 am
Nonstop2h 50m
Chicago Midway
Tue 3/24
2:35 pm-5:45 pm
Nonstop2h 10m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 2/28
5:15 pm-7:23 pm
Nonstop3h 08m
Chicago O'Hare Intl
Mon 3/2
7:05 am-10:37 am
Nonstop2h 32m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 2/5
3:35 pm-5:43 pm
Nonstop3h 08m
Chicago O'Hare Intl
Mon 2/9
7:40 am-11:05 am
Nonstop2h 25m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 2/25
7:00 am-9:10 am
Nonstop3h 10m
Chicago O'Hare Intl
Thu 2/26
10:00 am-1:20 pm
Nonstop2h 20m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 2/2
9:30 am-11:34 am
Nonstop3h 04m
Chicago O'Hare Intl
Mon 2/2
4:15 pm-7:39 pm
Nonstop2h 24m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 2/26
7:15 am-9:28 am
Nonstop3h 13m
Chicago O'Hare Intl
Sat 2/28
7:05 am-10:37 am
Nonstop2h 32m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 4/8
7:10 am-9:10 am
Nonstop3h 00m
Chicago O'Hare Intl
Wed 4/15
6:00 am-9:15 am
Nonstop2h 15m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 2/9
6:21 pm-8:25 pm
Nonstop3h 04m
Chicago O'Hare Intl
Tue 2/10
7:30 am-10:52 am
Nonstop2h 22m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 2/3
3:35 pm-5:43 pm
Nonstop3h 08m
Chicago O'Hare Intl
Thu 2/5
7:40 am-11:05 am
Nonstop2h 25m
$135
Showing 1-10 of 60 results
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, April is the cheapest month in which you can book a flight from Boston to Illinois (average of $89). Flying from Boston to Illinois in January is currently the most expensive (average of $126). 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 January 27, 2026.
One of the essential ways to save on airfare from Boston to Illinois is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 21% on airfare.
What is the cheapest day to fly from Boston to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Boston to Illinois. Price data was last updated on January 24, 2026.
Travelers seeking maximum savings on their Boston to Illinois flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 January 27, 2026.
The most flights from BOS to USIL are scheduled on a Sunday (60 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (29 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 January 27, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines 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.
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Boston to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Boston to Illinois
Discover the top 6 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 January 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$45 | Average$145 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$68 | Average$178 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$80 | Average$281 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$219 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$117 | Average$392 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$128 | Average$425 | FlexibilityNo cancel fee | On-time71% |