MDW

$68 Find Cheap Flights from Massachusetts to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 2/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$133
Overall average: $219
Southwest
sáb 2/28sáb 3/7
BOS - MDW • Non-stop
Cheapest one-way
$68
Typical prices: $108-$166
Southwest
dom 2/8
BOS - MDW • Non-stop
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We hope you love your trip to Midway!
Flight Deals
Useful Info
Flight Deals

Cheap Flights from Massachusetts to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Massachusetts to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Massachusetts to Midway

sáb, fev 28 - sáb, mar 7
Southwest Logo
5:15 am - 7:00 am
BOS
-
MDW
2h 45mnonstop
Southwest Logo
6:45 pm - 10:00 pm
MDW
-
BOS
2h 15mnonstop
$133Southwest
sáb, fev 28 - seg, mar 2
Southwest Logo
5:45 pm - 7:35 pm
BOS
-
MDW
2h 50mnonstop
Southwest Logo
6:35 pm - 9:50 pm
MDW
-
BOS
2h 15mnonstop
$135Southwest
dom, mar 1 - ter, mar 3
Southwest Logo
5:00 am - 6:55 am
BOS
-
MDW
2h 55mnonstop
Southwest Logo
2:00 pm - 5:10 pm
MDW
-
BOS
2h 10mnonstop
$138Southwest
sáb, fev 28 - seg, mar 2
Delta Logo
5:50 am - 11:03 am
BOS
-
MDW
6h 13m
1 stop
Delta Logo
6:20 pm - 11:26 pm
MDW
-
BOS
4h 06m
1 stop
$139Delta
sáb, fev 28 - seg, mar 2
Delta Logo
9:00 am - 12:46 pm
BOS
-
MDW
4h 46m
1 stop
Delta Logo
6:20 pm - 11:26 pm
MDW
-
BOS
4h 06m
1 stop
$140Delta
qua, fev 11 - dom, fev 15
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
6:35 pm - 9:50 pm
MDW
-
BOS
2h 15mnonstop
$141Southwest
seg, fev 9 - qui, fev 12
Frontier Logo
6:00 am - 10:19 pm
BOS
-
MDW
17h 19m
1 stop
Frontier Logo
6:25 am - 1:13 am
MDW
-
BOS
17h 48m
1 stop
$145Frontier
sex, mai 1 - seg, mai 4
Frontier Logo
8:08 pm - 4:13 pm
BDL
-
MDW
21h 05m
1 stop
Frontier Logo
9:14 am - 7:17 pm
MDW
-
BDL
9h 03m
1 stop
$236Frontier
qui, fev 26 - qui, mar 5
Multiple Airlines Logo
2:27 pm - 10:29 pm
BDL
-
MDW
9h 02m
1 stop
Multiple Airlines Logo
5:16 pm - 5:08 pm
MDW
-
BDL
22h 52m
2 stops
$254Multiple Airlines
seg, fev 9 - qui, fev 12
Multiple Airlines Logo
7:05 am - 7:07 pm
BDL
-
MDW
37h 02m
2 stops
Multiple Airlines Logo
6:25 am - 1:32 pm
MDW
-
BDL
6h 07m
1 stop
$257Multiple Airlines
Useful Info

Good to know

Low seasonDecember
Cheapest flight$68
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly with an average 3% increase in price.
Flight from Boston to Chicago Midway Airport

FAQs for booking Massachusetts to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Massachusetts to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Massachusetts to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Massachusetts to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Massachusetts is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Massachusetts to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Massachusetts with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Massachusetts to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)