Cheap Flight Tickets from Chicago (CHI) to Boston (BOS), Starting at $99

Good to Know: Cheapest and Fastest CHI - BOS Flights

Useful information for finding best airline tickets from Chicago All Airport to Logan International on your next trip.

Cheapest Round Trip Flight

$99

WN Southwest Airlines • 1 stop • 11h 45m

Aug 12 – Aug 16

The cheapest round trip flight from Chicago to Boston (CHI-BOS-CHI) is currently $99

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Cheapest Direct Flight

$321

UA United Airlines • nonstop • 3h 53m

Aug 10

The cheapest nonstop flight from Chicago to Boston (CHI-BOS) is currently $321

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Fastest Flight

3h 47m

The fastest nonstop flight from Chicago to Boston (CHI-BOS) takes 3h 47m

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

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

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

Aug 12 - Aug 16, Economy
WN
Chicago → Boston
11h 45m
9:00 AM - 5:05 PM • 1 stop
WN
Chicago → Boston
8h 30m
5:55 AM - 10:05 AM • 1 stop
$99
Southwest Airlines
Aug 12 - Aug 16, Economy
WN
Chicago → Boston
6h 55m
9:25 AM - 2:40 PM • 1 stop
WN
Chicago → Boston
8h 30m
5:55 AM - 10:05 AM • 1 stop
$108
Southwest Airlines
Aug 09 - Aug 18, Economy
DL
Chicago → Boston
13h 45m
5:30 AM - 2:55 PM • 1 stop
F9
Chicago → Boston
13h 43m
12:45 PM - 8:08 PM • 1 stop
$277
Delta Airlines
Aug 12 - Aug 16, Economy
B6
Chicago → Boston
3h 47m
11:01 AM - 2:28 PM • nonstop
B6
Chicago → Boston
4h 16m
8:10 AM - 10:06 AM • nonstop
$333
JetBlue Airways
Aug 12 - Aug 16, Economy
UA
Chicago → Boston
4h 1m
1:55 PM - 5:36 PM • nonstop
UA
Chicago → Boston
4h 11m
10:38 AM - 12:29 PM • nonstop
$373
United Airlines
Aug 12 - Aug 16, Economy
DL
Chicago → Boston
8h 59m
5:20 PM - 11:59 PM • 1 stop
DL
Chicago → Boston
7h 13m
9:06 AM - 12:39 PM • 1 stop
$413
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?
ORD,MDW
What’s the most popular airline flying from CHI to BOS?
The most popular airline flying from Chicago to Boston are
Can I fly from CHI to BOS non-stop?
Yes, you can fly CHI 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 CHI to BOS Airport?
The earliest flight leaves CHI 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 CHI 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 CHI to BOS, which is 866.65 miles by air.
Which airlines provide the cheapest flights from Chicago (CHI) to Boston (BOS) ?
In the past couple of days, the cheapest tickets to BOS from CHI were found on WN : USD 99
Do I need a passport to fly between CHI and BOS?
No
What’s the latest departure time from CHI to BOS ?
The last flight leaves CHI at 9:41 pm

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

Origin Airport Chicago All Airport, Chicago, US
Destination Airport Logan International, Boston, US
Distance 867 miles

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