Cheap Flight Tickets from Chicago (MDW) to Boston (BOS), Starting at $322

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

$322

WN Southwest Airlines • nonstop • 3h 45m

Oct 09 – Oct 15

The cheapest round trip flight from Chicago to Boston (MDW-BOS-MDW) is currently $322

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Cheapest Direct Flight

$322

WN Southwest Airlines • nonstop • 3h 45m

Oct 09

The cheapest nonstop flight from Chicago to Boston (MDW-BOS) is currently $322

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Fastest Flight

3h 35m

The fastest nonstop flight from Chicago to Boston (MDW-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

American Airlines, AA

American 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 09 - Oct 15, Economy
WN
Chicago → Boston
3h 45m
5:30 AM - 8:55 AM • nonstop
WN
Chicago → Boston
3h 55m
10:00 PM - 11:35 PM • nonstop
$322
Southwest Airlines
Oct 09 - Oct 15, Economy
WN
Chicago → Boston
17h
8:55 PM - 8:15 AM • 1 stop
WN
Chicago → Boston
3h 55m
5:50 AM - 7:25 AM • nonstop
$351
Southwest Airlines
Oct 09 - Oct 15, Economy
WN
Chicago → Boston
8h 50m
2:50 PM - 9:20 PM • 2 stops
WN
Chicago → Boston
17h 10m
9:45 PM - 7:15 AM • 1 stop
$404
Southwest Airlines
Oct 09 - Oct 15, Economy
WN
Chicago → Boston
8h 50m
12:45 PM - 7:15 PM • 1 stop
WN
Chicago → Boston
3h 55m
5:50 AM - 7:25 AM • nonstop
$450
Southwest Airlines
Oct 09 - Oct 15, Economy
DL
Chicago → Boston
6h 55m
6:44 PM - 11:59 PM • 1 stop
DL
Chicago → Boston
7h 18m
5:39 AM - 9:17 AM • 1 stop
$456
Delta Airlines
Oct 09 - Oct 15, Economy
WN
Chicago → Boston
3h 40m
7:50 AM - 11:10 AM • nonstop
WN
Chicago → Boston
3h 55m
5:50 AM - 7:25 AM • nonstop
$513
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 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 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 456
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 8:55 pm

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

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

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