Cheap Flight Tickets from Chicago (CHI) to Boston (BOS), Starting at $140

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

$397

UA United Airlines • nonstop • 3h 57m

Jul 01 – Jul 02

The cheapest round trip flight from Chicago to Boston (CHI-BOS-CHI) is currently $397

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Cheapest Direct Flight

$140

B6 JetBlue Airways • nonstop • 3h 46m

Jul 02

The cheapest nonstop flight from Chicago to Boston (CHI-BOS) is currently $140

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Fastest Flight

3h 35m

The fastest nonstop flight from Chicago to Boston (CHI-BOS) takes 3h 35m

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 (CHI) to Boston (BOS)

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

Jul 01 - Jul 02, Economy
UA
Chicago → Boston
3h 57m
10:30 AM - 2:07 PM • nonstop
UA
Chicago → Boston
4h 18m
7:19 AM - 9:17 AM • nonstop
$397
United Airlines
Jul 02 - Jul 09, Economy
G4
Chicago → Boston
22h 31m
9:19 AM - 12:10 AM • 2 stops
B6
Chicago → Boston
4h 16m
8:10 AM - 10:06 AM • nonstop
$647
Allegiant
Jul 02 - Jul 03, Economy
SY
Chicago → Boston
23h 48m
6:05 PM - 9:33 AM • 1 stop
SY
Chicago → Boston
10h 24m
11:55 AM - 5:19 PM • 1 stop
$799
Sun Country Airlines
Jul 02 - Jul 09, Economy
F9
Chicago → Boston
30h 54m
9:48 PM - 5:42 PM • 2 stops
B6
Chicago → Boston
4h 16m
8:10 AM - 10:06 AM • nonstop
$965
Frontier Airlines
Jul 01 - Jul 02, Economy
F9
Chicago → Boston
13h 31m
12:04 PM - 9:15 PM • 1 stop
G4
Chicago → Boston
98h 25m
12:06 PM - 10:11 PM • 3 stops
$1175
Frontier Airlines
Jul 02 - Jul 02, Economy
DL
Chicago → Boston
13h 40m
5:30 AM - 3:20 PM • 1 stop
DL
Chicago → Boston
4h 17m
8:45 PM - 10:42 PM • nonstop
$1337
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 G4 : USD 647
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 9:48 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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