Cheap Flight Tickets from Boston (BOS) to Chicago (ORD), Starting at $122

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

$366

DL Delta Airlines • nonstop • 4h 17m

Jul 06 – Jul 13

The cheapest round trip flight from Boston to Chicago (BOS-ORD-BOS) is currently $366

🔍 Search Flights

Cheapest One way Flight

$207

DL Delta Airlines • 1 stop • 11h 55m

Jul 24

The cheapest one way flight from Boston to Chicago (BOS-ORD) is currently $207

🔍 Search Flights

Cheapest Direct Flight

$145

AA American Airlines • nonstop • 4h 14m

Jul 06

The cheapest nonstop flight from Boston to Chicago (BOS-ORD) is currently $145

🔍 Search Flights

Fastest Flight

4h 14m

The fastest nonstop flight from Boston to Chicago (BOS-ORD) takes 4h 14m

Top Airlines Flying from Boston to Chicago

Delta Airline, DL

Delta Airlines

Sun Country Airlines (SY)

Sun Country Airlines

American Airlines, AA

American Airlines

Alaska Airlines -AS

Alaska Airlines

Southwest Airlines-WN

Southwest Airlines

TAP Air Portugal Airline (TP)

TAP - Air Portugal

United Airlines, UA

United 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.

Jul 06 - Jul 13, Economy
DL
Boston → Chicago
4h 17m
8:45 PM - 10:42 PM • nonstop
DL
Boston → Chicago
3h 55m
7:25 PM - 11:00 PM • nonstop
$366
Delta Airlines
Jul 06 - Jul 13, Economy
DL
Boston → Chicago
6h 56m
1:10 PM - 4:26 PM • 1 stop
DL
Boston → Chicago
3h 55m
7:25 PM - 11:00 PM • nonstop
$386
Delta Airlines
Jul 06 - Jul 13, Economy
DL
Boston → Chicago
7h 25m
9:15 AM - 1:00 PM • 1 stop
DL
Boston → Chicago
3h 51m
10:28 AM - 1:59 PM • nonstop
$386
Delta Airlines
Jul 06 - Jul 13, Economy
DL
Boston → Chicago
9h 3m
5:05 PM - 9:48 PM • 1 stop
DL
Boston → Chicago
3h 51m
10:28 AM - 1:59 PM • nonstop
$386
Delta Airlines
Jul 06 - Jul 13, Economy
DL
Boston → Chicago
8h 33m
9:00 AM - 1:13 PM • 1 stop
DL
Boston → Chicago
3h 51m
6:59 AM - 10:30 AM • nonstop
$386
Delta Airlines
Jul 06 - Jul 13, Economy
SY
Boston → Chicago
9h 19m
12:05 PM - 5:04 PM • 1 stop
SY
Boston → Chicago
24h 12m
6:31 PM - 10:23 AM • 1 stop
$447
Sun Country 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 5:10 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 207
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 8:45 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

More Flight Options for Boston (BOS) and Chicago (ORD)

Why Fareleaders for BOS to ORD Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Boston to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on BOS to ORD flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Boston to Chicago flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Boston (BOS) to Chicago (ORD)
Terms and Conditions*