MDW

$59 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 6/1. 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.
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Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Massachusetts to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Massachusetts to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
5:45 am - 7:20 amBOS-MDW
2h 35mnonstop
Southwest Logo
6:50 am - 10:05 amMDW-BOS
2h 15mnonstop
$117Southwest
Find Deal
Thu, May 29 - Sun, Jun 1
Southwest Logo
6:25 pm - 10:25 pmBOS-MDW
5h 00m1 stop
Southwest Logo
6:00 am - 9:15 amMDW-BOS
2h 15mnonstop
$127Southwest
Find Deal
Sat, Jun 7 - Sun, Jun 8
Southwest Logo
5:45 am - 1:20 pmBOS-MDW
8h 35m2 stops
Southwest Logo
8:30 pm - 11:45 pmMDW-BOS
2h 15mnonstop
$132Southwest
Find Deal
Tue, Jun 10 - Fri, Jun 13
Delta Logo
6:15 am - 1:15 pmBDL-MDW
8h 00m1 stop
Delta Logo
6:20 pm - 11:04 pmMDW-BDL
3h 44m1 stop
$197Delta
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Sun, Jun 1 - Thu, Jun 19
Frontier Logo
3:56 pm - 10:02 pmBDL-MDW
7h 06m1 stop
Frontier Logo
6:10 am - 2:58 pmMDW-BDL
7h 48m1 stop
$198Frontier
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Sat, May 24 - Sat, May 31
Frontier Logo
10:45 am - 10:36 pmBOS-MDW
12h 51m1 stop
Frontier Logo
9:12 pm - 8:35 amMDW-BOS
10h 23m1 stop
$208Frontier
Find Deal
Wed, May 28 - Sun, Jun 1
Delta Logo
5:35 am - 8:39 amBDL-MDW
4h 04m1 stop
Delta Logo
6:00 am - 12:07 pmMDW-BDL
5h 07m1 stop
$245Delta
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Sun, Jul 20 - Sat, Jul 26
Allegiant Air Logo
11:31 am - 12:25 pmBOS-MDW
25h 54m1 stop
Allegiant Air Logo
2:54 pm - 9:14 amMDW-BOS
17h 20m1 stop
$250Allegiant Air
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Thu, May 22 - Mon, May 26
Logo
11:31 am - 2:26 pmBOS-MDW
27h 55m1 stop
Logo
8:04 pm - 9:09 amMDW-BOS
36h 05m3 stops
$268
Find Deal
Sun, Jun 1 - Mon, Jun 2
Logo
7:15 am - 3:37 pmBDL-MDW
33h 22m2 stops
Logo
8:09 pm - 9:01 amMDW-BDL
35h 52m3 stops
$535
Find Deal
Tue, Jun 10 - Thu, Jun 12
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Good to know

Low seasonJanuary
High seasonMay
Cheapest flight$59
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 4% 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.

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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