MDW

$62 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 6/18. 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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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, Aug 7 - Sun, Aug 10
Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
Southwest Logo
10:00 am - 1:25 pmMDW-BOS
2h 25mnonstop
$123Southwest
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Fri, Aug 22 - Sun, Aug 24
Southwest Logo
6:30 pm - 8:15 pmBOS-MDW
2h 45mnonstop
Southwest Logo
5:55 am - 9:10 amMDW-BOS
2h 15mnonstop
$125Southwest
Find Deal
Thu, Aug 7 - Mon, Aug 11
Allegiant Air Logo
11:31 am - 7:13 amBOS-MDW
20h 42m1 stop
Allegiant Air Logo
2:46 pm - 9:15 amMDW-BOS
17h 29m1 stop
$201Allegiant Air
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Sun, Jun 29 - Wed, Jul 2
Allegiant Air Logo
11:31 am - 7:15 amBOS-MDW
20h 44m1 stop
Allegiant Air Logo
9:03 am - 10:41 amMDW-BOS
24h 38m1 stop
$211Allegiant Air
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Sat, Aug 16 - Wed, Aug 20
Delta Logo
5:35 am - 8:35 amBDL-MDW
4h 00m1 stop
Delta Logo
9:31 am - 4:10 pmMDW-BDL
5h 39m1 stop
$224Delta
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Sun, Aug 31 - Wed, Sep 3
Delta Logo
1:00 pm - 6:37 pmBDL-MDW
6h 37m1 stop
Delta Logo
10:11 am - 5:59 pmMDW-BDL
6h 48m1 stop
$245Delta
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Thu, Aug 7 - Mon, Aug 11
Logo
11:31 am - 7:13 amBOS-MDW
20h 42m1 stop
Logo
8:03 am - 9:42 pmMDW-BOS
36h 39m3 stops
$251
Find Deal
Fri, Sep 5 - Mon, Sep 8
Logo
8:59 am - 4:43 pmBOS-MDW
8h 44m1 stop
Logo
12:50 pm - 10:30 amMDW-BOS
20h 40m2 stops
$259
Find Deal
Sat, Aug 16 - Mon, Aug 18
Frontier Logo
12:27 pm - 10:35 pmBDL-MDW
11h 08m1 stop
Frontier Logo
8:35 am - 7:53 pmMDW-BDL
10h 18m1 stop
$267Frontier
Find Deal
Sat, Jun 28 - Thu, Jul 3
Frontier Logo
9:40 am - 8:17 pmBOS-MDW
11h 37m1 stop
Frontier Logo
4:06 pm - 12:43 amMDW-BOS
7h 37m1 stop
$270Frontier
Find Deal
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Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$62
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 1% 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.

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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