Cheap Flight Tickets from Boston (BOS) to Chicago (MDW), Starting at $336

Good to Know: Cheapest and Fastest BOS - MDW Flights

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

Cheapest Round Trip Flight

$342

WN Southwest Airlines • 1 stop • 8h 55m

Jul 23 – Jul 29

The cheapest round trip flight from Boston to Chicago (BOS-MDW-BOS) is currently $342

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Cheapest Direct Flight

$336

WN Southwest Airlines • nonstop • 3h 55m

Jul 23

The cheapest nonstop flight from Boston to Chicago (BOS-MDW) is currently $336

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Fastest Flight

3h 55m

The fastest nonstop flight from Boston to Chicago (BOS-MDW) takes 3h 55m

Top Airlines Flying from Boston to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

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

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

Jul 23 - Jul 29, Economy
WN
Boston → Chicago
8h 55m
8:55 AM - 1:30 PM • 1 stop
WN
Boston → Chicago
3h 40m
6:05 PM - 9:25 PM • nonstop
$342
Southwest Airlines
Jul 23 - Jul 29, Economy
WN
Boston → Chicago
9h
2:20 PM - 7:00 PM • 1 stop
WN
Boston → Chicago
3h 40m
2:40 PM - 6:00 PM • nonstop
$342
Southwest Airlines
Jul 23 - Jul 29, Economy
WN
Boston → Chicago
8h 30m
8:00 PM - 12:10 AM • 1 stop
WN
Boston → Chicago
3h 35m
9:00 AM - 12:15 PM • nonstop
$342
Southwest Airlines
Jul 23 - Jul 29, Economy
WN
Boston → Chicago
7h 25m
12:55 PM - 4:40 PM • 1 stop
WN
Boston → Chicago
7h 5m
11:25 AM - 4:50 PM • 1 stop
$462
Southwest Airlines
Jul 23 - Jul 29, Economy
WN
Boston → Chicago
7h 25m
1:25 PM - 5:10 PM • 1 stop
WN
Boston → Chicago
7h 5m
11:25 AM - 4:50 PM • 1 stop
$504
Southwest Airlines
Jul 23 - Jul 29, Economy
WN
Boston → Chicago
11h 45m
3:55 PM - 10:00 PM • 1 stop
WN
Boston → Chicago
7h 5m
11:25 AM - 4:50 PM • 1 stop
$612
Southwest Airlines

Fly from Boston to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Boston to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Boston to Chicago Flights

What are the airports in Boston?
BOS
What’s the most popular airline flying from BOS to MDW?
The most popular airline flying from Boston to Chicago are
Can I fly from BOS to MDW non-stop?
Yes, you can fly BOS to MDW non-stop on
Which airlines fly nonstop between Boston and Chicago?
The non-stop flights between Boston and Chicago are .
What’s the earliest departure time from BOS to MDW Airport?
The earliest flight leaves BOS at 5:25 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my Boston to Chicago 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 BOS to MDW?
Read the fare rules of the Boston to Chicago 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 Boston and Chicago?
operate flights between Boston and Chicago
How long does a flight from Boston to Chicago take?
It takes approximately 2 hour to fly non-stop from BOS to MDW, which is 860.68 miles by air.
Which airlines provide the cheapest flights from Boston (BOS) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from BOS were found on WN : USD 462
Do I need a passport to fly between BOS and MDW?
No
What’s the latest departure time from BOS to MDW ?
The last flight leaves BOS at 8:00 pm

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

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

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