Cheap Flight Tickets from Boston (BOS) to Chicago (ORD), Starting at $229

Good to Know: Cheapest and Fastest BOS - ORD Flights

Useful information for finding best airline tickets from Logan International to Chicago O'Hare International on your next trip.

Cheapest Round Trip Flight

$229

DL Delta Airlines • nonstop • 4h 15m

Oct 13 – Oct 14

The cheapest round trip flight from Boston to Chicago (BOS-ORD-BOS) is currently $229

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Cheapest Direct Flight

$229

DL Delta Airlines • nonstop • 4h 15m

Oct 13

The cheapest nonstop flight from Boston to Chicago (BOS-ORD) is currently $229

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Fastest Flight

3h 55m

The fastest nonstop flight from Boston to Chicago (BOS-ORD) takes 3h 55m

Top Airlines Flying from Boston to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Alaska Airlines -AS

Alaska Airlines

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

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

Oct 13 - Oct 14, Economy
DL
Boston → Chicago
4h 15m
4:25 PM - 6:20 PM • nonstop
DL
Boston → Chicago
3h 55m
7:25 AM - 11:00 AM • nonstop
$229
Delta Airlines
Oct 13 - Oct 14, Economy
DL
Boston → Chicago
8h 58m
5:05 PM - 9:43 PM • 1 stop
DL
Boston → Chicago
4h 3m
7:10 PM - 10:53 PM • nonstop
$233
Delta Airlines
Oct 13 - Oct 14, Economy
DL
Boston → Chicago
10h 50m
5:50 AM - 11:40 AM • 1 stop
DL
Boston → Chicago
8h 50m
5:29 PM - 11:59 PM • 1 stop
$238
Delta Airlines
Oct 13 - Oct 14, Economy
DL
Boston → Chicago
7h 24m
9:15 AM - 12:59 PM • 1 stop
DL
Boston → Chicago
12h 4m
6:30 AM - 2:54 PM • 1 stop
$238
Delta Airlines
Oct 13 - Oct 14, Economy
WN
Boston → Chicago
3h 55m
7:20 AM - 8:55 AM • nonstop
WN
Boston → Chicago
3h 40m
1:10 PM - 4:30 PM • nonstop
$570
Southwest Airlines
Oct 13 - Oct 14, Economy
WN
Boston → Chicago
3h 55m
12:55 PM - 2:30 PM • nonstop
WN
Boston → Chicago
3h 40m
6:10 PM - 9:30 PM • nonstop
$570
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 ORD?
The most popular airline flying from Boston to Chicago are
Can I fly from BOS to ORD non-stop?
Yes, you can fly BOS to ORD 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 ORD Airport?
The earliest flight leaves BOS at 5:50 am and lands in ORD - Chicago O'Hare International
What are the airports in Chicago?
MDW,ORD
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 ORD?
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 ORD, which is 866.65 miles by air.
Which airlines provide the cheapest flights from Boston (BOS) to Chicago (ORD) ?
In the past couple of days, the cheapest tickets to ORD from BOS were found on DL : USD 238
Do I need a passport to fly between BOS and ORD?
No
What’s the latest departure time from BOS to ORD ?
The last flight leaves BOS at 5:05 pm

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

Origin Airport Logan International, Boston, US
Destination Airport Chicago O'Hare International , Chicago, US
Distance 867 miles

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