Cheap Flight Tickets from Chicago (MDW) to Boston (BOS), Starting at $537

Good to Know: Cheapest and Fastest MDW - BOS Flights

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

Cheapest Round Trip Flight

$547

DL Delta Airlines • 1 stop • 6h 55m

Oct 27 – Nov 03

The cheapest round trip flight from Chicago to Boston (MDW-BOS-MDW) is currently $547

🔍 Search Flights

Cheapest Direct Flight

$537

WN Southwest Airlines • nonstop • 3h 40m

Oct 27

The cheapest nonstop flight from Chicago to Boston (MDW-BOS) is currently $537

🔍 Search Flights

Fastest Flight

3h 40m

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

Top Airlines Flying from Chicago to Boston

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

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

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

Oct 27 - Nov 03, Economy
DL
Chicago → Boston
6h 55m
6:44 PM - 11:59 PM • 1 stop
DL
Chicago → Boston
4h 14m
7:30 AM - 9:24 AM • nonstop
$547
Delta Airlines
Oct 27 - Nov 03, Economy
WN
Chicago → Boston
10h 55m
8:10 AM - 4:05 PM • 1 stop
WN
Chicago → Boston
4h 5m
5:55 PM - 7:40 PM • nonstop
$547
Southwest Airlines
Oct 27 - Nov 03, Economy
WN
Chicago → Boston
3h 40m
7:50 AM - 11:10 AM • nonstop
WN
Chicago → Boston
7h 30m
5:35 PM - 9:25 PM • 1 stop
$547
Southwest Airlines
Oct 27 - Nov 03, Economy
WN
Chicago → Boston
3h 40m
9:10 AM - 12:30 PM • nonstop
WN
Chicago → Boston
7h 30m
5:35 PM - 9:25 PM • 1 stop
$547
Southwest Airlines
Oct 27 - Nov 03, Economy
WN
Chicago → Boston
3h 40m
3:15 PM - 6:35 PM • nonstop
WN
Chicago → Boston
10h 30m
9:10 AM - 2:40 PM • 1 stop
$547
Southwest Airlines
Oct 27 - Nov 03, Economy
WN
Chicago → Boston
7h 30m
8:15 AM - 2:05 PM • 1 stop
WN
Chicago → Boston
8h 45m
5:05 PM - 9:30 PM • 1 stop
$556
Southwest 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 MDW to BOS?
The most popular airline flying from Chicago to Boston are
Can I fly from MDW to BOS non-stop?
Yes, you can fly MDW 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 MDW to BOS Airport?
The earliest flight leaves MDW at 7:50 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 MDW 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 MDW to BOS, which is 860.68 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to Boston (BOS) ?
In the past couple of days, the cheapest tickets to BOS from MDW were found on DL : USD 547
Do I need a passport to fly between MDW and BOS?
No
What’s the latest departure time from MDW to BOS ?
The last flight leaves MDW at 6:44 pm

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

Origin Airport Chicago Midway International , Chicago, US
Destination Airport Logan International, Boston, US
Distance 861 miles

More Flight Options for Chicago (MDW) and Boston (BOS)

Why Fareleaders for MDW to BOS Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Chicago to Boston flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on MDW to BOS flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Chicago to Boston flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Chicago (MDW) to Boston (BOS)
Terms and Conditions*