Search & Compare - Boston to Chicago Flights & Tickets

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Cheap flights from Boston to Chicago (BOS to CHI)

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.

Good to know

Useful information for finding cheap flights from Logan International to Chicago All Airport and booking your next trip

Cheapest Round Trip Flight

$185

AA American Airlines • 1 stop • 11h 46m

Aug 20 – Aug 24

The cheapest round trip flight from Logan International to Chicago All Airport is currently $185

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Fastest Flight

4h 11m

The fastest nonstop flight from Logan International to Chicago All Airport takes 4h 11m

Recent airfare deals on Boston to Chicago

Aug 20 - Aug 24, Economy
AA
Boston → Chicago
11h 46m
9:22 AM - 3:28 PM • 1 stop
AA
Boston → Chicago
3h 48m
6:15 AM - 9:43 AM • nonstop
American Airlines
Aug 20 - Aug 24, Economy
NK
Boston → Chicago
15h 44m
11:56 AM - 8:40 PM • 1 stop
NK
Boston → Chicago
30h 1m
3:29 PM - 10:30 AM • 1 stop
Spirit Airlines
Aug 20 - Aug 24, Economy
UA
Boston → Chicago
22h 16m
8:02 PM - 8:38 AM • 1 stop
UA
Boston → Chicago
10h 24m
6:00 AM - 1:24 PM • 1 stop
United Airlines
Aug 20 - Aug 24, Economy
DL
Boston → Chicago
4h 11m
11:34 AM - 1:25 PM • nonstop
DL
Boston → Chicago
9h 13m
5:00 PM - 11:53 PM • 1 stop
Delta Airlines
Aug 20 - Aug 24, Economy
DL
Boston → Chicago
4h 15m
7:20 AM - 9:15 AM • nonstop
DL
Boston → Chicago
8h 43m
11:00 AM - 5:23 PM • 1 stop
Delta Airlines
Aug 20 - Aug 24, Economy
WN
Boston → Chicago
17h 20m
7:05 AM - 4:45 PM • 1 stop
WN
Boston → Chicago
18h 45m
12:40 PM - 1:05 AM • 1 stop
Southwest Airlines

Facts to know while booking flights from Boston to Chicago

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 7:05 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 ('WN') : USD 293
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 8:02 pm

Flights from Boston to Chicago

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

Popular Airlines

Popular Origin & Destination

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