Cheap Flight Tickets from Boston (BOS) to Chicago (MDW), Starting at $131

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

$135

WN Southwest Airlines • 1 stop • 12h 5m

Sep 21 – Sep 28

The cheapest round trip flight from Boston to Chicago (BOS-MDW-BOS) is currently $135

🔍 Search Flights

Cheapest Direct Flight

$131

WN Southwest Airlines • nonstop • 3h 55m

Sep 21

The cheapest nonstop flight from Boston to Chicago (BOS-MDW) is currently $131

🔍 Search Flights

Fastest Flight

3h 50m

The fastest nonstop flight from Boston to Chicago (BOS-MDW) takes 3h 50m

Top Airlines Flying from Boston to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American 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.

Sep 21 - Sep 28, Economy
WN
Boston → Chicago
12h 5m
7:40 AM - 2:05 PM • 1 stop
WN
Boston → Chicago
3h 35m
6:30 AM - 9:45 AM • nonstop
$135
Southwest Airlines
Sep 21 - Sep 28, Economy
WN
Boston → Chicago
7h 20m
5:50 AM - 9:30 AM • 1 stop
WN
Boston → Chicago
3h 45m
6:30 PM - 9:55 PM • nonstop
$135
Southwest Airlines
Sep 21 - Sep 28, Economy
WN
Boston → Chicago
12h 5m
10:30 AM - 4:55 PM • 1 stop
WN
Boston → Chicago
3h 35m
6:30 AM - 9:45 AM • nonstop
$135
Southwest Airlines
Sep 21 - Sep 28, Economy
DL
Boston → Chicago
12h 4m
5:30 AM - 11:54 AM • 1 stop
DL
Boston → Chicago
5h 57m
7:01 PM - 11:58 PM • 1 stop
$267
Delta Airlines
Sep 21 - Sep 28, Economy
DL
Boston → Chicago
10h 5m
8:15 AM - 1:20 PM • 1 stop
DL
Boston → Chicago
11h 53m
2:00 PM - 10:13 PM • 1 stop
$389
Delta Airlines
Sep 21 - Sep 28, Economy
DL
Boston → Chicago
11h 55m
7:05 AM - 1:20 PM • 1 stop
DL
Boston → Chicago
11h 53m
2:00 PM - 10:13 PM • 1 stop
$389
Delta 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 5:30 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 135
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 8:20 pm

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

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

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

Why Fareleaders for BOS to MDW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Boston to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on BOS to MDW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Boston to Chicago 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 Boston (BOS) to Chicago (MDW)
Terms and Conditions*