Cheap Flights from Chicago to Boston Starting at $56

Helping travelers to find the best flight offers

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.

Airfare from Chicago to Boston by month

Airlines operating on route

Starting at $56

Starting at $56

Starting at $57

Starting at $59

Starting at $61

Starting at $64

Starting at $126

Direct Flights from Chicago to Boston

Boston city image

ChicagoBoston

CHIBOS

05/10/2025

Departure date

Direct flight

United Airlines

UA1532

Starting at $159

Boston city image

ChicagoBoston

CHIBOS

05/11/2025

Departure date

Direct flight

United Airlines

UA2067

Starting at $68

Boston city image

ChicagoBoston

CHIBOS

05/18/2025

Departure date

Direct flight

Southwest Airlines

WN1915

Starting at $187

Boston city image

ChicagoBoston

CHIBOS

05/21/2025

Departure date

Direct flight

Southwest Airlines

WN1240

Starting at $125

Boston city image

ChicagoBoston

CHIBOS

05/23/2025

Departure date

Direct flight

American Airlines

AA3010

Starting at $273

Boston city image

ChicagoBoston

CHIBOS

05/27/2025

Departure date

Direct flight

Southwest Airlines

WN3273

Starting at $181

Boston city image

ChicagoBoston

CHIBOS

06/13/2025

Departure date

Direct flight

American Airlines

AA2682

Starting at $101

Boston city image

ChicagoBoston

CHIBOS

06/27/2025

Departure date

Direct flight

Southwest Airlines

WN3786

Starting at $212

Boston city image

ChicagoBoston

CHIBOS

07/25/2025

Departure date

Direct flight

American Airlines

AA547

Starting at $105

Boston city image

ChicagoBoston

CHIBOS

09/24/2025

Departure date

Direct flight

JetBlue Airways

B6312

Starting at $62

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:

Chicago airports overview

ORD
+2
United Airlines
JetBlue Airways
American Airlines
Airlines flying to this airport
$56
Starting at
$90-53%
on average
MDW
Southwest Airlines
Airlines flying to this airport
$138
Starting at
$138
on average

Boston airports overview

BOS
+3
United Airlines
JetBlue Airways
American Airlines
Airlines flying to this airport
$56
Starting at
$91-12%
on average
PSM
Spirit Airlines
Airlines flying to this airport
$102
Starting at
$102
on average

Frequently asked questions (FAQ)

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

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.

Alternative routes