Cheap Flight Tickets from Boston (BOS) to Chicago (CHI), Starting at $135

Good to Know: Cheapest and Fastest BOS - CHI Flights

Useful information for finding best airline tickets from Logan International to Chicago All Airport on your next trip.

Cheapest Round Trip Flight

$159

AA American Airlines • nonstop • 5h 6m

Aug 13 – Aug 16

The cheapest round trip flight from Boston to Chicago (BOS-CHI-BOS) is currently $159

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Cheapest Direct Flight

$135

WN Southwest Airlines • nonstop • 3h 50m

Sep 17

The cheapest nonstop flight from Boston to Chicago (BOS-CHI) is currently $135

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Fastest Flight

3h 50m

The fastest nonstop flight from Boston to Chicago (BOS-CHI) takes 3h 50m

Top Airlines Flying from Boston to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

Sun Country Airlines (SY)

Sun Country Airlines

American Airlines, AA

American Airlines

Alaska Airlines -AS

Alaska Airlines

Latest Flight Deals from Boston (BOS) to Chicago (CHI)

Compare and book low fare round-trip air tickets from Boston to Chicago. Ideal for travelers with confirmed return itineraries.

Aug 13 - Aug 16, Economy
AA
Boston → Chicago
5h 6m
7:10 AM - 9:16 AM • nonstop
AA
Boston → Chicago
3h 53m
11:30 AM - 3:03 PM • nonstop
$159
American Airlines
Sep 17 - Sep 17, Economy
AA
Boston → Chicago
7h
8:25 AM - 12:50 PM • 1 stop
AA
Boston → Chicago
5h 59m
3:00 PM - 9:49 PM • 1 stop
$274
American Airlines
Sep 17 - Sep 17, Economy
AA
Boston → Chicago
7h 29m
12:16 PM - 4:05 PM • 1 stop
AA
Boston → Chicago
7h 18m
5:48 PM - 11:26 PM • 1 stop
$311
American Airlines
Aug 13 - Aug 16, Economy
DL
Boston → Chicago
4h 14m
12:25 PM - 2:19 PM • nonstop
DL
Boston → Chicago
8h 37m
7:05 AM - 1:22 PM • 1 stop
$406
Delta Airlines
Aug 13 - Aug 16, Economy
AA
Boston → Chicago
8h 32m
6:00 AM - 11:12 AM • 1 stop
AA
Boston → Chicago
3h 49m
8:30 PM - 11:59 PM • nonstop
$407
American Airlines
Sep 17 - Sep 20, Economy
WN
Boston → Chicago
12h 35m
4:30 PM - 11:25 PM • 1 stop
WN
Boston → Chicago
14h 5m
1:55 PM - 11:40 PM • 1 stop
$1126
Southwest Airlines

Fly from Boston to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Boston to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Boston to Chicago Flights

What are the airports in Boston?
BOS
What’s the most popular airline flying from BOS to CHI?
The most popular airline flying from Boston to Chicago are
Can I fly from BOS to CHI non-stop?
Yes, you can fly BOS to CHI non-stop on
Which airlines fly nonstop between Boston and Chicago?
The non-stop flights between Boston and Chicago are .
What’s the earliest departure time from BOS to CHI Airport?
The earliest flight leaves BOS at 6:00 am and lands in CHI - Chicago All Airport
What are the airports in Chicago?
ORD,MDW
Can I make changes to my Boston to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from BOS to CHI?
Read the fare rules of the Boston to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Boston and Chicago?
operate flights between Boston and Chicago
How long does a flight from Boston to Chicago take?
It takes approximately 2 hour to fly non-stop from BOS to CHI, which is 866.65 miles by air.
Which airlines provide the cheapest flights from Boston (BOS) to Chicago (CHI) ?
In the past couple of days, the cheapest tickets to CHI from BOS were found on AA : USD 311
Do I need a passport to fly between BOS and CHI?
No
What’s the latest departure time from BOS to CHI ?
The last flight leaves BOS at 1:400 pm

Boston (BOS) to Chicago (CHI): Airport Information

Origin Airport Logan International, Boston, US
Destination Airport Chicago All Airport, Chicago, US
Distance 867 miles

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