Cheap Flight Tickets from Chicago (ORD) to Boston (BOS), Starting at $211

Good to Know: Cheapest and Fastest ORD - BOS Flights

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

Cheapest Round Trip Flight

$507

DL Delta Airlines • 1 stop • 5h 55m

Oct 11 – Oct 19

The cheapest round trip flight from Chicago to Boston (ORD-BOS-ORD) is currently $507

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Cheapest One way Flight

$211

AA American Airlines • 1 stop • 15h 49m

Oct 12

The cheapest one way flight from Chicago to Boston (ORD-BOS) is currently $211

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Cheapest Direct Flight

$397

B6 JetBlue Airways • nonstop • 3h 48m

Oct 11

The cheapest nonstop flight from Chicago to Boston (ORD-BOS) is currently $397

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Fastest Flight

11m

The fastest nonstop flight from Chicago to Boston (ORD-BOS) takes 11m

Top Airlines Flying from Chicago to Boston

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Sun Country Airlines (SY)

Sun Country Airlines

Alaska Airlines -AS

Alaska Airlines

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

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

Oct 11 - Oct 19, Economy
DL
Chicago → Boston
5h 55m
7:00 AM - 11:55 AM • 1 stop
DL
Chicago → Boston
4h 11m
7:40 PM - 9:31 PM • nonstop
$507
Delta Airlines
Oct 11 - Oct 19, Economy
DL
Chicago → Boston
8h 20m
11:30 AM - 5:30 PM • 1 stop
DL
Chicago → Boston
4h 11m
7:40 PM - 9:31 PM • nonstop
$507
Delta Airlines
Oct 11 - Oct 19, Economy
DL
Chicago → Boston
3h 50m
10:24 AM - 1:54 PM • nonstop
DL
Chicago → Boston
8h 33m
7:27 AM - 11:40 AM • 1 stop
$507
Delta Airlines
Oct 11 - Oct 19, Economy
WN
Chicago → Boston
3h 40m
2:45 PM - 6:05 PM • nonstop
WN
Chicago → Boston
4h
10:00 PM - 11:40 PM • nonstop
$529
Southwest Airlines
Oct 13 - Oct 18, Economy
DL
Chicago → Boston
4h 3m
7:10 PM - 10:53 PM • nonstop
DL
Chicago → Boston
4h 14m
7:30 AM - 9:24 AM • nonstop
$627
Delta Airlines
Oct 13 - Oct 18, Economy
DL
Chicago → Boston
8h 50m
5:29 PM - 11:59 PM • 1 stop
DL
Chicago → Boston
4h 14m
7:30 AM - 9:24 AM • nonstop
$637
Delta Airlines

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

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

FAQs on Chicago to Boston Flights

What are the airports in Chicago?
MDW,ORD
What’s the most popular airline flying from ORD to BOS?
The most popular airline flying from Chicago to Boston are
Can I fly from ORD to BOS non-stop?
Yes, you can fly ORD to BOS non-stop on
Which airlines fly nonstop between Chicago and Boston?
The non-stop flights between Chicago and Boston are .
What’s the earliest departure time from ORD to BOS Airport?
The earliest flight leaves ORD at 7:00 am and lands in BOS - Logan International
What are the airports in Boston?
BOS
Can I make changes to my Chicago to Boston 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 ORD to BOS?
Read the fare rules of the Chicago to Boston 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 Chicago and Boston?
operate flights between Chicago and Boston
How long does a flight from Chicago to Boston take?
It takes approximately 2 hour to fly non-stop from ORD to BOS, which is 866.65 miles by air.
Which airlines provide the cheapest flights from Chicago (ORD) to Boston (BOS) ?
In the past couple of days, the cheapest tickets to BOS from ORD were found on UA : USD 492
Do I need a passport to fly between ORD and BOS?
No
What’s the latest departure time from ORD to BOS ?
The last flight leaves ORD at 8:18 pm

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

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

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