Cheap Flights from Chicago to Boston

Cheapest flights from Chicago to Boston

Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Chicago to Boston. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.

Cheapest one way flight

$94

JetBlue Airways

Direct flight

2h 31m

06/20/2026

The cheapest one-way flight from Chicago to Boston departs on 06/20/2026, is operated by JetBlue Airways and costs $94

Cheapest round trip flight

$171

Southwest Airlines

Direct flight

6h 35m

07/14/2026

The cheapest roundtrip flight from Chicago to Boston departs on 07/14/2026, is operated by Southwest Airlines and costs $171

The fastest flight

2h 10m

Fastest flight from Chicago to Boston takes 2h 10m

Direct flights

Several times a week

There are direct flights on this route 5 days a week: Su, Tu, We, Fr, and Sa

Distance

1365km

Timezone difference

1h

The distance between Chicago and Boston is 1365km (846 miles). The time difference between Chicago and Boston is 1h

Remember that on average the ideal time to book flights is 2 months before departure!

Airfare from Chicago to Boston by month

The minimum one-way ticket price from Chicago to Boston is $94 (June 2026), while the maximum is $124 (September 2026). On average, a ticket costs $101–$104.

June 2026

Lowest price

on average:

$94

September 2026

Highest price

on average:

$124

Avg Price

Price dynamics

Ticket prices for Chicago — Boston follow a predictable curve: rise, peak, and decline. This typical seasonal pattern lets you plan your purchase to avoid overpaying.

Cheaper and more expensive periods

Prices rise from June 2026 to September 2026 (+32%), then decline from September 2026 to December 2026 (18%). The cheapest tickets are in June 2026–July 2026 (averaging $96), while the priciest are in September 2026–December 2026 ($112).

Best time to buy

For savings, plan your flight for June 2026–July 2026 — you could save up to 14%. Try to avoid September 2026–December 2026 when possible: prices are at their highest then.

Price predictability

Price spread on this route is 11%. Costs depend heavily on the season, so flexibility in choosing your departure month is especially valuable here.

Airlines operating on route

The Chicago — Boston route is served by a wide range of airlines: 4 in total, including JetBlue Airways, American Airlines, United Airlines, and Southwest Airlines. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $94. Our service helps compare all available offers within seconds and choose the most convenient option. You can filter flights by price, departure time, or baggage rules to make your trip as comfortable as possible. With so many airlines, there’s always a chance to catch special promotions and save.

starting at $94

starting at $95

starting at $95

starting at $113

Non-stop flights from Chicago to Boston

A non-stop flight is the most convenient and comfortable way to fly from Chicago to Boston, despite the fact that sometimes flights with transfers can cost significantly less.

Chicago — Boston

CHI — BOS

06/20/2026

Departure

Direct flight

B61012

starting at $94

Chicago — Boston

CHI — BOS

06/23/2026

Departure

Direct flight

AA2968

starting at $95

Chicago — Boston

CHI — BOS

06/30/2026

Departure

Direct flight

UA1186

starting at $95

Chicago — Boston

CHI — BOS

06/19/2026

Departure

Direct flight

AA2682

starting at $96

Chicago — Boston

CHI — BOS

07/17/2026

Departure

Direct flight

UA1779

starting at $99

Chicago — Boston

CHI — BOS

12/09/2026

Departure

Direct flight

UA2331

starting at $101

Chicago — Boston

CHI — BOS

07/25/2026

Departure

Direct flight

AA1554

starting at $104

Chicago — Boston

CHI — BOS

06/24/2026

Departure

Direct flight

AA3022

starting at $110

Chicago — Boston

CHI — BOS

06/06/2026

Departure

Direct flight

WN4611

starting at $113

Chicago — Boston

CHI — BOS

06/07/2026

Departure

Direct flight

WN4611

starting at $114

Schedule of direct flights from Chicago to Boston

The only airline operating direct flights from Chicago to Boston is American Airlines. Flights operate on Sunday and Thursday.

American Airlines

Su and Th

starting at $261

Chicago airports overview

Merrill C Meigs

•

CGX

3km

DuPage Airport

•

DPA

52km

Chicago Midway International Airport

•

MDW

14km

O'Hare International Airport

•

ORD

26km

Chicago Executive Airport

•

PWK

35km

Chicago Rockford International Airport

•

RFD

140km

•

Boston airports overview

Logan International Airport

•

BOS

4km

Pease Air Force Base

•

PSM

93km

•

Frequently asked questions (FAQ)

Answers to questions about the route that travelers are most interested in.

What is the cheapest price for flights from Chicago to Boston?

The cheapest flight ticket from Chicago to Boston according to data for the last 48 hours costs $94

When is the best time to buy air tickets on the route Chicago — Boston?

Often the best time to buy tickets from Chicago to Boston is 2 months before departure.

When is the cheapest time of year to fly from Chicago to Boston?

Based on statistics over the past years, the lowest prices for flights from Chicago to Boston can be found flying in these months: June, July, December.

How long does it take to fly from Chicago to Boston?

The fastest flights from Chicago to Boston start from 2 hours 10 minutes in the air.

Which airline can fly direct from Chicago to Boston?

The following airlines operate direct flights on the route Chicago — Boston: JetBlue Airways, American Airlines, United Airlines

Special offers and sales on air tickets from Chicago to Boston

We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.

We couldn't find any special offers for flights from Chicago to Boston

Alternative routes

Appleton ➜ Boston•Kalamazoo ➜ Boston•Champaign ➜ Boston•Fort Wayne ➜ Boston•Indianapolis ➜ Boston•Lansing ➜ Boston•Milwaukee ➜ Boston•Muskegon ➜ Boston•South Bend ➜ Boston•Chicago ➜ New Bedford•Chicago ➜ New Haven•Chicago ➜ Manchester•Chicago ➜ New York•Chicago ➜ Providence•Chicago ➜ Portland•Chicago ➜ Stamford

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Cheapest one way flight

$94

JetBlue Airways

Direct flight

2h 31m

06/20/2026

The cheapest one-way flight from Chicago to Boston departs on 06/20/2026, is operated by JetBlue Airways and costs $94

Cheapest round trip flight

$171

Southwest Airlines

Direct flight

6h 35m

07/14/2026

The cheapest roundtrip flight from Chicago to Boston departs on 07/14/2026, is operated by Southwest Airlines and costs $171

The fastest flight