MDW

$69 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 9/22. 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

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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

Thu, Oct 2 - Mon, Oct 6
Southwest Logo
5:35 am - 10:15 amBOS-MDW
5h 40m1 stop
Southwest Logo
9:20 pm - 12:40 amMDW-BOS
2h 20mnonstop
$127Southwest
Find Deal
Thu, Oct 2 - Mon, Oct 6
Southwest Logo
5:35 am - 1:20 pmBOS-MDW
8h 45m2 stops
Southwest Logo
5:50 pm - 9:05 pmMDW-BOS
2h 15mnonstop
$132Southwest
Find Deal
Thu, Oct 30 - Sun, Nov 2
Southwest Logo
5:15 am - 6:55 amBOS-MDW
2h 40mnonstop
Southwest Logo
9:10 am - 6:10 pmMDW-BOS
8h 00m1 stop
$133Southwest
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Sat, Sep 20 - Sun, Sep 21
Southwest Logo
5:50 am - 7:25 amBOS-MDW
2h 35mnonstop
Southwest Logo
5:55 am - 9:10 amMDW-BOS
2h 15mnonstop
$137Southwest
Find Deal
Thu, Oct 30 - Sun, Nov 2
Frontier Logo
10:04 am - 6:39 pmBOS-MDW
9h 35m1 stop
Frontier Logo
10:12 am - 8:28 amMDW-BOS
21h 16m1 stop
$155Frontier
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Wed, Dec 10 - Mon, Dec 15
Frontier Logo
6:00 am - 9:32 pmBOS-MDW
16h 32m1 stop
Frontier Logo
6:00 am - 12:44 amMDW-BOS
17h 44m1 stop
$160Frontier
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Sun, Oct 5 - Tue, Oct 7
Delta Logo
5:35 am - 8:40 amBDL-MDW
4h 05m1 stop
Delta Logo
6:23 pm - 11:14 pmMDW-BDL
3h 51m1 stop
$197Delta
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Wed, Oct 29 - Wed, Nov 5
Logo
8:05 am - 9:12 amBDL-MDW
26h 07m1 stop
Logo
2:06 pm - 9:42 amMDW-BDL
18h 36m1 stop
$200
Find Deal
Thu, Oct 30 - Mon, Nov 3
Logo
9:39 am - 2:33 pmBOS-MDW
5h 54m1 stop
Logo
1:37 pm - 11:16 amMDW-BOS
20h 39m2 stops
$201
Find Deal
Sun, Oct 5 - Tue, Oct 7
Delta Logo
5:35 am - 8:40 amBDL-MDW
4h 05m1 stop
Delta Logo
6:23 pm - 11:14 pmMDW-BDL
3h 51m1 stop
$232Delta
Find Deal

Everything you should know

Cheapest round-trip
$127
Overall average: $234
Southwest
Thu 10/2Mon 10/6
BOS - MDW • 1 stop
Cheapest non-stop
$137
Typical prices: $188-328
Southwest
Fri 9/26Sun 9/28
BOS - MDW • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$69
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 11% lower on average.
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
Valparaiso
Lansing
Munster
Chesterton
Schererville
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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