MDW

$61 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 11/10. 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

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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, Dec 4 - Thu, Dec 11
Frontier Logo
11:28 am - 6:08 pmBOS-MDW
7h 40m1 stop
Frontier Logo
7:23 pm - 10:22 amMDW-BOS
13h 59m1 stop
$124Frontier
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Thu, Nov 13 - Fri, Nov 14
Frontier Logo
9:39 am - 2:33 pmBOS-MDW
5h 54m1 stop
Frontier Logo
3:27 pm - 8:28 amMDW-BOS
16h 01m1 stop
$136Frontier
Find Deal
Thu, Nov 13 - Sun, Nov 16
Southwest Logo
5:15 am - 7:00 amBOS-MDW
2h 45mnonstop
Southwest Logo
5:00 am - 12:50 pmMDW-BOS
6h 50m1 stop
$137Southwest
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Mon, Nov 24 - Thu, Dec 4
Frontier Logo
8:24 am - 6:06 pmBOS-MDW
10h 42m1 stop
Frontier Logo
7:23 pm - 10:22 amMDW-BOS
13h 59m1 stop
$141Frontier
Find Deal
Fri, Nov 21 - Mon, Nov 24
Southwest Logo
6:55 pm - 8:45 pmBOS-MDW
2h 50mnonstop
Southwest Logo
7:15 pm - 10:30 pmMDW-BOS
2h 15mnonstop
$142Southwest
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Mon, Nov 10 - Mon, Nov 10
Southwest Logo
5:15 am - 7:00 amBOS-MDW
2h 45mnonstop
Southwest Logo
2:25 pm - 5:40 pmMDW-BOS
2h 15mnonstop
$147Southwest
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Sat, Jan 24 - Fri, Jan 30
Multiple Airlines Logo
6:00 am - 11:25 pmBOS-MDW
18h 25m1 stop
Multiple Airlines Logo
8:56 pm - 1:04 amMDW-BOS
27h 08m2 stops
$158Multiple Airlines
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Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
11:28 am - 6:08 pmBOS-MDW
7h 40m1 stop
Multiple Airlines Logo
6:37 pm - 10:03 amMDW-BOS
14h 26m1 stop
$165Multiple Airlines
Find Deal
Tue, Nov 11 - Tue, Nov 18
Delta Logo
6:00 am - 11:52 amBDL-MDW
6h 52m1 stop
Delta Logo
12:47 pm - 9:05 pmMDW-BDL
7h 18m1 stop
$242Delta
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Wed, Dec 17 - Tue, Jan 20
Delta Logo
6:09 am - 1:10 pmBDL-MDW
8h 01m1 stop
Delta Logo
12:48 pm - 9:11 pmMDW-BDL
7h 23m1 stop
$245Delta
Find Deal

Everything you should know

Cheapest round-trip
$124
Overall average: $218
Frontier
Thu 12/4Thu 12/11
BOS - MDW • 1 stop
Cheapest non-stop
$141
Typical prices: $187-$312
Southwest
Sat 2/7Mon 2/9
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 seasonFebruary
Cheapest flight$61
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 0% 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
Lansing
Valparaiso
Chesterton
Schererville
Munster
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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