Cheap Flight Tickets from Boston (BOS) to Chicago (ORD), Starting at $152

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

$179

DL Delta Airlines • nonstop • 4h 11m

Oct 12 – Oct 17

The cheapest round trip flight from Boston to Chicago (BOS-ORD-BOS) is currently $179

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Cheapest One way Flight

$230

AS Alaska Airlines • 1 stop • 33h 25m

Aug 27

The cheapest one way flight from Boston to Chicago (BOS-ORD) is currently $230

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Cheapest Direct Flight

$152

DL Delta Airlines • nonstop • 4h 11m

Oct 12

The cheapest nonstop flight from Boston to Chicago (BOS-ORD) is currently $152

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Fastest Flight

4h 10m

The fastest nonstop flight from Boston to Chicago (BOS-ORD) takes 4h 10m

Top Airlines Flying from Boston to Chicago

Alaska Airlines -AS

Alaska Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Southwest Airlines-WN

Southwest Airlines

Sun Country Airlines (SY)

Sun Country 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 12 - Oct 17, Economy
DL
Boston → Chicago
4h 11m
7:40 PM - 9:31 PM • nonstop
DL
Boston → Chicago
8h 37m
5:42 PM - 11:59 PM • 1 stop
$179
Delta Airlines
Oct 12 - Oct 17, Economy
DL
Boston → Chicago
4h 15m
4:25 PM - 6:20 PM • nonstop
DL
Boston → Chicago
19h 16m
6:44 PM - 7:40 AM • 2 stops
$211
Delta Airlines
Oct 12 - Oct 17, Economy
DL
Boston → Chicago
4h 14m
7:30 AM - 9:24 AM • nonstop
DL
Boston → Chicago
8h 37m
5:42 PM - 11:59 PM • 1 stop
$214
Delta Airlines
Oct 12 - Oct 17, Economy
DL
Boston → Chicago
8h 37m
6:00 PM - 10:17 PM • 1 stop
DL
Boston → Chicago
12h 3m
7:00 AM - 3:23 PM • 1 stop
$426
Delta Airlines
Oct 12 - Oct 17, Economy
DL
Boston → Chicago
8h 53m
12:00 PM - 4:33 PM • 1 stop
DL
Boston → Chicago
12h 3m
7:00 AM - 3:23 PM • 1 stop
$426
Delta Airlines
Oct 12 - Oct 17, Economy
DL
Boston → Chicago
8h 28m
9:00 AM - 1:08 PM • 1 stop
DL
Boston → Chicago
12h 3m
7:00 AM - 3:23 PM • 1 stop
$510
Delta 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 7:12 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 AS : USD 230
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 8:50 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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