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

$74

JetBlue Airways

Direct flight

2h 28m

12/09/2025

The cheapest one-way flight from Chicago to Boston departs on 12/09/2025, is operated by JetBlue Airways and costs $74

Cheapest round trip flight

$126

JetBlue Airways

Direct flight

5h 9m

12/11/2025

The cheapest roundtrip flight from Chicago to Boston departs on 12/11/2025, is operated by JetBlue Airways and costs $126

The fastest flight

2h 15m

Fastest flight from Chicago to Boston takes 2h 15m

Direct flights

Several times a week

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

Earliest flight

6:10 AM

Latest flight

8:40 PM

Average flight duration

2h 36m

Direct flights count

156

Distance

1365km

Timezone difference

1h

The distance between Chicago and Boston is 1365km (846 miles). The average flight duration is 2h 36m. There are 156 direct flights from Chicago to Boston. The time difference between Chicago and Boston is 1h. Flights from Chicago begin at 6:10 AM. The latest flight from Chicago departs at 8:40 PM

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

Airfare from Chicago to Boston by month

We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Chicago to Boston

April 2026

Lowest price

on average:

$133

Avg Price

Airlines operating on route

The Chicago — Boston route is served by a wide range of airlines: 5 in total, including JetBlue Airways, Southwest Airlines, United Airlines, American Airlines, and Envoy Air. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $74. 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 $74

Starting at $75

Starting at $127

Starting at $92

Starting at $210

Direct Flights from Chicago to Boston

A direct 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

12/19/2025

Departure

Direct flight

B61012

Starting at $125

Chicago — Boston

CHI — BOS

12/09/2025

Departure

Direct flight

WN3678

Starting at $152

Chicago — Boston

CHI — BOS

12/20/2025

Departure

Direct flight

UA2067

Starting at $194

Chicago — Boston

CHI — BOS

12/24/2025

Departure

Direct flight

UA1693

Starting at $144

Chicago — Boston

CHI — BOS

12/30/2025

Departure

Direct flight

AA867

Starting at $210

Chicago — Boston

CHI — BOS

01/02/2026

Departure

Direct flight

B61012

Starting at $216

Chicago — Boston

CHI — BOS

01/03/2026

Departure

Direct flight

UA2106

Starting at $290

Chicago — Boston

CHI — BOS

01/03/2026

Departure

Direct flight

WN3680

Starting at $285

Chicago — Boston

CHI — BOS

01/04/2026

Departure

Direct flight

MQ3710

Starting at $210

Chicago — Boston

CHI — BOS

01/05/2026

Departure

Direct flight

AA867

Starting at $136

Schedule of direct flights from Chicago to Boston

A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to Boston:

American Airlines

Every day

Starting at $187

United Airlines

Every day

Starting at $221

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.

How much is the cheapest flight ticket from Chicago to Boston?

The cheapest flight ticket from Chicago to Boston according to data for the last 48 hours costs $74

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: April.

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

The fastest flights from Chicago to Boston start from 2 hours 15 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, Southwest 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

$74

JetBlue Airways

Direct flight

2h 28m

12/09/2025

The cheapest one-way flight from Chicago to Boston departs on 12/09/2025, is operated by JetBlue Airways and costs $74

Cheapest round trip flight

$126

JetBlue Airways

Direct flight

5h 9m

12/11/2025

The cheapest roundtrip flight from Chicago to Boston departs on 12/11/2025, is operated by JetBlue Airways and costs $126

The fastest flight