Cheap Business Class Flights from Chicago to Boston
CHI — BOS
Aug 20 — Aug 271
Round-trip
1 adult, Business
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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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Essential info for Business Class flights from Chicago to Boston
Find the latest flights to Boston in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 2,558,603 searches and data were last updated on July 21, 2026.
Top Rated Airline | American Airlines |
|---|---|
No. of Airlines | 6 |
Arrival Airport | Boston Logan Intl Airport |
Find Business Class flight deals from Chicago to Boston
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Cheapest business class flights to BostonExplore the most affordable business class flight options available to Boston. Find the lowest fares based on data from user searches, with prices last updated on July 21, 2026.
Explore the most affordable business class flight options available to Boston. Find the lowest fares based on data from user searches, with prices last updated on July 21, 2026.
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:00 am
ORD
- BOS
Nonstop2h 39m
American Airlines
Tue 9/297:00 am
BOS
- ORD
Nonstop3h 06m
American Airlines
Deal found 7/21![American Airlines logo]()
$487
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:05 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Wed 8/126:14 am
BOS
- ORD
Nonstop3h 06m
American Airlines
Deal found 7/21![American Airlines logo]()
$503
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:00 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Wed 8/127:17 pm
BOS
- ORD
Nonstop3h 18m
American Airlines
Deal found 7/21![American Airlines logo]()
$508
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:00 am
ORD
- BOS
Nonstop2h 39m
American Airlines
Wed 9/235:45 pm
BOS
- ORD
Nonstop3h 20m
American Airlines
Deal found 7/21![American Airlines logo]()
$512
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:00 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Thu 8/135:45 pm
BOS
- ORD
Nonstop3h 19m
American Airlines
Deal found 7/21![American Airlines logo]()
$529
This KAYAK deal was found by Cheapflights users on 7/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:00 am
ORD
- BOS
1 stop5h 37m
American Airlines
Sun 11/225:41 am
BOS
- ORD
Nonstop3h 18m
American Airlines
Deal found 7/20![American Airlines logo]()
$538
Best business class flights to BostonDiscover carefully curated business class flight deals to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 21, 2026.
Discover carefully curated business class flight deals to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 21, 2026.
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/148:30 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Sat 8/157:24 am
BOS
- ORD
Nonstop3h 06m
American Airlines
Deal found 7/21![American Airlines logo]()
$503
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:30 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Sat 8/227:24 am
BOS
- ORD
Nonstop3h 06m
American Airlines
Deal found 7/21![American Airlines logo]()
$503
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:00 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Thu 8/207:10 am
BOS
- ORD
Nonstop3h 06m
American Airlines
Deal found 7/21![American Airlines logo]()
$503
This KAYAK deal was found by Cheapflights users on 7/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:00 am
ORD
- BOS
1 stop5h 37m
American Airlines
Sun 11/225:41 am
BOS
- ORD
Nonstop3h 18m
American Airlines
Deal found 7/20![American Airlines logo]()
$538
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:00 am
ORD
- BOS
1 stop4h 25m
American Airlines
Mon 9/287:44 pm
BOS
- ORD
1 stop4h 52m
American Airlines
Deal found 7/21![American Airlines logo]()
$641
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:00 am
ORD
- BOS
1 stop4h 25m
American Airlines
Sun 9/276:00 am
BOS
- ORD
Nonstop3h 10m
American Airlines
Deal found 7/21![American Airlines logo]()
$701
This KAYAK deal was found by Cheapflights users on 7/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:30 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Deal found 7/18![American Airlines logo]()
$252
This KAYAK deal was found by Cheapflights users on 7/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:00 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Deal found 7/20![American Airlines logo]()
$252
This KAYAK deal was found by Cheapflights users on 7/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/268:29 pm
ORD
- BOS
Nonstop2h 36m
American Airlines
Deal found 7/20![American Airlines logo]()
$262
This KAYAK deal was found by Cheapflights users on 7/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/34:45 pm
ORD
- BOS
1 stop6h 52m
American Airlines
Deal found 7/20![American Airlines logo]()
$376
This Alaska Airlines deal was found by Cheapflights users on 7/18. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:00 am
ORD
- BOS
1 stop22h 39m
Alaska Airlines
Deal found 7/18![Alaska Airlines logo]()
$1,565
This KAYAK deal was found by Cheapflights users on 7/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:12 pm
ORD
- BOS
2 stops16h 28m
Alaska Airlines
Deal found 7/20![Alaska Airlines logo]()
$1,953
One-way business class flights to BostonSearch for one-way business class flight options to Boston. Find affordable one-way fares based on user searches. Data last updated July 21, 2026.
Search for one-way business class flight options to Boston. Find affordable one-way fares based on user searches. Data last updated July 21, 2026.
This KAYAK deal was found by Cheapflights users on 7/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:30 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Deal found 7/17![American Airlines logo]()
$252
This KAYAK deal was found by Cheapflights users on 7/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/268:29 pm
ORD
- BOS
Nonstop2h 36m
American Airlines
Deal found 7/20![American Airlines logo]()
$262
This KAYAK deal was found by Cheapflights users on 7/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/34:45 pm
ORD
- BOS
1 stop6h 52m
American Airlines
Deal found 7/20![American Airlines logo]()
$376
This Alaska Airlines deal was found by Cheapflights users on 7/18. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:00 am
ORD
- BOS
1 stop22h 39m
Alaska Airlines
Deal found 7/18![Alaska Airlines logo]()
$1,565
This KAYAK deal was found by Cheapflights users on 7/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:12 pm
ORD
- BOS
2 stops16h 28m
Alaska Airlines
Deal found 7/18![Alaska Airlines logo]()
$1,943
This KAYAK deal was found by Cheapflights users on 7/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/32:12 pm
ORD
- BOS
2 stops16h 28m
Alaska Airlines
Deal found 7/20![Alaska Airlines logo]()
$2,143
Quickest business class flights to BostonExplore quickest business class flight options to Boston based on user searches, and compare prices and availability for your desired travel dates. Data last updated July 21, 2026.
Explore quickest business class flight options to Boston based on user searches, and compare prices and availability for your desired travel dates. Data last updated July 21, 2026.
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:05 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Wed 8/126:14 am
BOS
- ORD
Nonstop3h 06m
American Airlines
Deal found 7/21![American Airlines logo]()
$503
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:00 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Wed 8/127:17 pm
BOS
- ORD
Nonstop3h 18m
American Airlines
Deal found 7/21![American Airlines logo]()
$508
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:00 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Thu 8/135:45 pm
BOS
- ORD
Nonstop3h 19m
American Airlines
Deal found 7/21![American Airlines logo]()
$529
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:05 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Fri 8/217:24 pm
BOS
- ORD
1 stop5h 20m
American Airlines
Deal found 7/21![American Airlines logo]()
$572
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:00 am
ORD
- BOS
Nonstop2h 39m
American Airlines
Tue 9/297:00 am
BOS
- ORD
Nonstop3h 06m
American Airlines
Deal found 7/21![American Airlines logo]()
$487
This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:00 am
ORD
- BOS
Nonstop2h 39m
American Airlines
Wed 9/235:45 pm
BOS
- ORD
Nonstop3h 20m
American Airlines
Deal found 7/21![American Airlines logo]()
$512
This KAYAK deal was found by Cheapflights users on 7/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:30 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Deal found 7/17![American Airlines logo]()
$252
This KAYAK deal was found by Cheapflights users on 7/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/268:29 pm
ORD
- BOS
Nonstop2h 36m
American Airlines
Deal found 7/20![American Airlines logo]()
$262
This KAYAK deal was found by Cheapflights users on 7/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/34:45 pm
ORD
- BOS
1 stop6h 52m
American Airlines
Deal found 7/20![American Airlines logo]()
$376
This KAYAK deal was found by Cheapflights users on 7/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:12 pm
ORD
- BOS
2 stops16h 28m
Alaska Airlines
Deal found 7/18![Alaska Airlines logo]()
$1,943
This KAYAK deal was found by Cheapflights users on 7/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/32:12 pm
ORD
- BOS
2 stops16h 28m
Alaska Airlines
Deal found 7/20![Alaska Airlines logo]()
$2,143
This Alaska Airlines deal was found by Cheapflights users on 7/18. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:00 am
ORD
- BOS
1 stop22h 39m
Alaska Airlines
Deal found 7/18![Alaska Airlines logo]()
$1,565
Travel insights for business class flights from Chicago to Boston
Get recent, data-driven insights about business class flights from Chicago to Boston including ideal travel times, pricing trends, and more.
Prices
Airlines
Which month is the cheapest to fly Business Class from Chicago to Boston?
For Business Class flights the cheapest month to fly the route is September. The most expensive months are December and April.
Which day of the week is best to fly business class from Chicago to Boston?
For the lowest prices, departures on Wednesday are best. Try to avoid leaving on a Saturday, as it's usually the most expensive day. For your return flight, Monday is the cheapest day to fly and Tuesday is the most expensive.
Frequently Asked Questions about Chicago to Boston Business Class flights
Find answers to common questions related to Business Class tickets for flights to Boston. Get information on booking, amenities, upgrade options, and more. This FAQ section was last updated on July 21, 2026.
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