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Cheap First Class Flights from Chicago to Boston

CHI — BOS
Aug 20 — Aug 271
Thu 8/20
Thu 8/27
1 adult, First
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Essential info for First 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
Most popular airline to fly first class with to Boston in the past 7 days
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Airlines that offer first class options for this route
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Closest airport for this route
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Find First Class flight deals from Chicago to Boston

Cheapest first class flights to Boston
Explore the most affordable first 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 7/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/134:00 pm
ORD
-
BOS
Nonstop2h 50m
American Airlines
Sun 8/167:10 am
BOS
-
ORD
Nonstop3h 06m
American Airlines
Deal found 7/17$490
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 8/198:26 am
ORD
-
BOS
Nonstop2h 36m
American Airlines
Sat 8/227:17 pm
BOS
-
ORD
Nonstop3h 18m
American Airlines
Deal found 7/21$495
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:55 pm
ORD
-
BOS
Nonstop2h 35m
United Airlines
Sat 9/268:31 pm
BOS
-
ORD
Nonstop2h 58m
United Airlines
Deal found 7/21$507
This United Airlines deal was found by Cheapflights users on 7/16. 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 12/254:10 pm
ORD
-
BOS
Nonstop2h 29m
United Airlines
Wed 12/309:30 am
BOS
-
ORD
Nonstop2h 55m
United Airlines
Deal found 7/16$515
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/209:40 pm
ORD
-
BOS
Nonstop2h 30m
United Airlines
Sat 9/268:31 pm
BOS
-
ORD
Nonstop2h 58m
United Airlines
Deal found 7/21$516
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:24 pm
ORD
-
BOS
Nonstop2h 35m
United Airlines
Tue 9/297:00 pm
BOS
-
ORD
1 stop5h 21m
United Airlines
Deal found 7/21$517

Travel insights for first class flights from Chicago to Boston

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

Which month is the cheapest to fly First Class from Chicago to Boston?

For First Class flights the cheapest month to fly the route is July. The most expensive months are August and September.

Which day of the week is best to fly first class from Chicago to Boston?

For the lowest prices, departures on Wednesday are best. Try to avoid leaving on a Monday, as it's usually the most expensive day. For your return flight, Monday is the cheapest day to fly and Saturday is the most expensive.

Frequently Asked Questions about Chicago to Boston First Class flights

Find answers to common questions related to First 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.

  • What's cheaper, flying business or first class?

    First class flights are more often than not more expensive than business class. However, average prices on this route are lower for first class at $607 compared to an average of $749 for business class tickets.

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