Cheap Flight Tickets from Chicago (ORD) to Boston (BOS), Starting at $145

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

$145

UA United Airlines • 1 stop • 5h 56m

Jul 11 – Jul 15

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

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Cheapest Direct Flight

$261

UA United Airlines • nonstop • 4h 2m

Jul 10

The cheapest nonstop flight from Chicago to Boston (ORD-BOS) is currently $261

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Fastest Flight

3h 40m

The fastest nonstop flight from Chicago to Boston (ORD-BOS) takes 3h 40m

Top Airlines Flying from Chicago to Boston

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

Sun Country Airlines (SY)

Sun Country Airlines

American Airlines, AA

American 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.

Jul 11 - Jul 15, Economy
UA
Chicago → Boston
5h 56m
11:15 AM - 7:14 PM • 1 stop
UA
Chicago → Boston
6h 45m
8:00 AM - 12:06 PM • 1 stop
$145
United Airlines
Jul 11 - Jul 15, Economy
UA
Chicago → Boston
5h 53m
1:30 PM - 7:28 PM • 1 stop
UA
Chicago → Boston
6h 45m
8:00 AM - 12:06 PM • 1 stop
$174
United Airlines
Jul 11 - Jul 15, Economy
DL
Chicago → Boston
6h 54m
11:12 AM - 4:26 PM • 1 stop
DL
Chicago → Boston
4h 14m
8:45 PM - 10:39 PM • nonstop
$219
Delta Airlines
Jul 10 - Jul 14, Economy
UA
Chicago → Boston
3h 56m
7:45 PM - 11:21 PM • nonstop
UA
Chicago → Boston
4h 12m
3:13 PM - 5:05 PM • nonstop
$279
United Airlines
Jul 10 - Jul 14, Economy
UA
Chicago → Boston
7h 24m
1:30 PM - 7:14 PM • 1 stop
UA
Chicago → Boston
7h 31m
5:45 AM - 9:36 AM • 1 stop
$347
United Airlines
Jul 10 - Jul 14, Economy
DL
Chicago → Boston
7h 36m
5:35 PM - 11:31 PM • 1 stop
DL
Chicago → Boston
4h 14m
8:45 PM - 10:39 PM • nonstop
$453
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 5:30 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 DL : USD 453
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 7:45 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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