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Cheap flights from Chicago Midway Airport to Massachusetts from $52

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Massachusetts departing on 1/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Massachusetts

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to Massachusetts that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to Massachusetts.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to Massachusetts? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Massachusetts, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to Massachusetts

Find recent round-trip train or bus tickets from Chicago Midway Airport to Massachusetts.

All round-trip flight deals to Massachusetts

The cheapest plane tickets to Massachusetts found on KAYAK recently.
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
5:45 am - 1:24 pmBOS-MDW
8h 39m1 stop
$103Frontier
Find Deal
Wed, Dec 11 - Wed, Dec 18
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
$104Frontier
Find Deal
Tue, Dec 10 - Wed, Dec 11
5:31 pm - 12:39 amMDW-BOS
6h 08m1 stop
6:00 am - 4:16 pmBOS-MDW
11h 16m1 stop
$105Frontier
Find Deal
Tue, Jan 21 - Tue, Jan 28
5:31 pm - 12:39 amMDW-BOS
6h 08m1 stop
6:00 am - 4:16 pmBOS-MDW
11h 16m1 stop
$106Frontier
Find Deal
Tue, Jan 21 - Tue, Jan 28
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
6:40 am - 8:25 amBOS-MDW
2h 45mnonstop
$158Southwest
Find Deal
Fri, Dec 13 - Sun, Dec 15
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
8:15 pm - 10:00 pmBOS-MDW
2h 45mnonstop
$179Southwest
Find Deal
Fri, Dec 13 - Sat, Jan 4
4:58 pm - 11:58 pmMDW-BDL
6h 00m1 stop
5:25 am - 8:58 amBDL-MDW
4h 33m1 stop
$276Delta
Find Deal
Tue, Dec 17 - Wed, Dec 18
6:00 am - 1:14 pmMDW-BDL
6h 14m1 stop
5:20 am - 8:54 amBDL-MDW
4h 34m1 stop
$286Delta
Find Deal
Wed, Jan 8 - Sat, Jan 11
6:31 pm - 10:42 pmMDW-BDL
27h 11m2 stops
6:00 am - 8:45 amBDL-MDW
27h 45m2 stops
$1,293
Find Deal
Sun, Dec 22 - Sat, Dec 28
5:35 pm - 10:42 pmMDW-BDL
28h 07m3 stops
8:05 am - 5:51 pmBDL-MDW
10h 46m2 stops
$1,296
Find Deal
Wed, Dec 25 - Sun, Dec 29
5:24 pm - 12:30 amMDW-BOS
6h 06m1 stop
$52Frontier
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Tue, Jan 14
5:24 pm - 12:30 amMDW-BOS
6h 06m1 stop
$53Frontier
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Tue, Jan 7
5:24 pm - 12:30 amMDW-BOS
6h 06m1 stop
$54Frontier
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Tue, Jan 7
10:05 am - 1:20 pmMDW-BOS
2h 15mnonstop
$79Southwest
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Mon, Feb 3
5:40 am - 8:55 amMDW-BOS
2h 15mnonstop
$95Southwest
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Thu, Nov 28
6:00 am - 11:59 amMDW-ALB
4h 59m1 stop
$136Delta
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Wed, Dec 18
4:50 pm - 12:11 amMDW-BDL
6h 21m1 stop
$138Delta
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Tue, Dec 24
9:21 am - 9:07 pmMDW-BOS
34h 46m3 stops
Tue, Jan 7
6:31 pm - 10:37 pmMDW-BDL
27h 06m3 stops
Sun, Jan 5
6:22 pm - 11:26 amMDW-ALB
16h 04m1 stop
$285Allegiant Air
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Sun, Feb 23
6:48 pm - 12:31 amMDW-BOS
4h 43m1 stop
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
$208Frontier
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Tue, Nov 26 - Tue, Dec 10
6:48 pm - 12:31 amMDW-BOS
4h 43m1 stop
12:38 pm - 9:02 pmBOS-MDW
9h 24m1 stop
$218Frontier
Find Deal
Tue, Nov 26 - Fri, Dec 6
6:05 am - 1:22 pmMDW-BDL
6h 17m1 stop
2:12 pm - 11:15 pmBDL-MDW
10h 03m1 stop
$225Frontier
Find Deal
Tue, Nov 26 - Thu, Nov 28
6:48 pm - 12:31 amMDW-BOS
4h 43m1 stop
6:00 am - 5:18 pmBOS-MDW
12h 18m1 stop
$228Frontier
Find Deal
Tue, Nov 26 - Thu, Dec 5
8:25 pm - 11:35 pmMDW-BOS
2h 10mnonstop
6:00 pm - 7:45 pmBOS-MDW
2h 45mnonstop
$303Southwest
Find Deal
Tue, Nov 26 - Tue, Dec 3
5:25 am - 11:35 amMDW-BOS
5h 10m1 stop
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
$312Southwest
Find Deal
Tue, Nov 26 - Tue, Dec 3
3:19 pm - 11:42 pmMDW-BOS
7h 23m1 stop
5:20 am - 8:58 amBOS-MDW
4h 38m1 stop
$341Delta
Find Deal
Tue, Nov 26 - Sun, Dec 8
4:55 pm - 12:58 amMDW-BOS
7h 03m1 stop
8:00 am - 1:35 pmBOS-MDW
6h 35m1 stop
$346Delta
Find Deal
Sat, Nov 23 - Wed, Nov 27
9:21 am - 8:50 pmMDW-BOS
34h 29m3 stops
10:38 am - 8:45 amBOS-MDW
23h 07m3 stops
Tue, Nov 26 - Tue, Dec 3
10:10 am - 8:04 amMDW-BOS
20h 54m2 stops
10:38 am - 8:45 amBOS-MDW
23h 07m3 stops
Tue, Nov 26 - Tue, Dec 3
8:05 am - 11:20 amMDW-BOS
2h 15mnonstop
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
$158Southwest
Find Deal
Sat, Dec 7 - Thu, Dec 12
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
8:15 pm - 10:00 pmBOS-MDW
2h 45mnonstop
$179Southwest
Find Deal
Fri, Dec 13 - Sat, Jan 4
8:00 am - 11:15 amMDW-BOS
2h 15mnonstop
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
$188Southwest
Find Deal
Sun, Dec 8 - Tue, Jan 7
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
8:00 pm - 9:45 pmBOS-MDW
2h 45mnonstop
$195Southwest
Find Deal
Wed, Dec 25 - Sun, Dec 29
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
6:25 am - 8:15 amBOS-MDW
2h 50mnonstop
$199Southwest
Find Deal
Wed, Dec 18 - Sun, Dec 29
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
5:50 am - 7:50 amBOS-MDW
3h 00mnonstop
$208Southwest
Find Deal
Wed, Dec 25 - Sat, Jan 11
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
$218Southwest
Find Deal
Wed, Dec 18 - Wed, Dec 25
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
$238Southwest
Find Deal
Wed, Dec 4 - Thu, Dec 5
8:25 pm - 11:35 pmMDW-BOS
2h 10mnonstop
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
$247Southwest
Find Deal
Mon, Dec 23 - Thu, Jan 23
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
$248Southwest
Find Deal
Tue, Dec 3 - Wed, Dec 4

Frontier flights from Chicago Midway Airport to Massachusetts

Our best Frontier deals on Chicago Midway Airport to Massachusetts flight tickets
Frontier
Dec 11
MDW12:57 pmChicago Midway
10h 33m
1 stop
BOS12:30 amBoston Logan Intl
Dec 18
BOS5:45 amBoston Logan Intl
8h 39m
1 stop
MDW1:24 pmChicago Midway
Frontier
Dec 10
MDW12:57 pmChicago Midway
10h 33m
1 stop
BOS12:30 amBoston Logan Intl
Dec 11
BOS6:00 amBoston Logan Intl
6h 42m
1 stop
MDW11:42 amChicago Midway
Frontier
Jan 21
MDW5:31 pmChicago Midway
6h 08m
1 stop
BOS12:39 amBoston Logan Intl
Jan 28
BOS6:00 amBoston Logan Intl
11h 16m
1 stop
MDW4:16 pmChicago Midway

Southwest flights from Chicago Midway Airport to Massachusetts

Our best Southwest deals on Chicago Midway Airport to Massachusetts flight tickets
Southwest
Dec 13
MDW8:30 pmChicago Midway
2h 10m
BOS11:40 pmBoston Logan Intl
Dec 15
BOS6:40 amBoston Logan Intl
2h 45m
MDW8:25 amChicago Midway
Southwest
Nov 28
MDW8:10 amChicago Midway
2h 15m
BOS11:25 amBoston Logan Intl
Dec 7
BOS5:05 amBoston Logan Intl
2h 50m
MDW6:55 amChicago Midway
Southwest
Dec 13
MDW8:30 pmChicago Midway
2h 10m
BOS11:40 pmBoston Logan Intl
Jan 4
BOS8:15 pmBoston Logan Intl
2h 45m
MDW10:00 pmChicago Midway

See travel insights to Massachusetts from

How to get the cheapest flight ticket from Chicago Midway Airport to Massachusetts

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Massachusetts?

According to our data, Wednesday is the cheapest day to fly to Massachusetts from Chicago Midway Airport. The lowest ticket price found for a Wednesday departure recently was $237. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Tuesday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $345.

What is the cheapest Chicago Midway to Massachusetts flight route?

Fly from Chicago Midway to Boston Logan Intl for the best Chicago Midway - Massachusetts flight prices

What cabin class options are available on Chicago Midway to Massachusetts flights?

There are 1 cabin classes available to choose from on Chicago Midway to Massachusetts flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Massachusetts flights?

You could potentially save up to 34% on your flight if you consider stops on a Chicago Midway Airport to Massachusetts flight.

Cheap Chicago Midway Airport to Massachusetts flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Massachusetts

Best Price Found

$52

Fastest flight time

1h 50m

Direct flights

Every day

Airports in Massachusetts

3 airports
The best one-way flight to Massachusetts from Chicago Midway Airport in the past 72 hours is $52. The best round-trip flight deal from Chicago Midway Airport to Massachusetts found on momondo in the last 72 hours is $103.
The fastest flight from Chicago Midway Airport to Massachusetts takes 1h 50m
Direct flights go from Chicago Midway Airport to Massachusetts every day.
There are 3 airports near Massachusetts: Boston Logan Intl (BOS), Albany Intl (ALB), Hartford Bradley Intl (BDL)

  • When did momondo last update prices for flights from Chicago Midway Airport to Massachusetts?

    Prices for flights from Chicago Midway Airport to Massachusetts are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to Massachusetts?

  • How old do you have to be to fly from Chicago Midway Airport to Massachusetts?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Massachusetts.

  • What documentation or ID do you need to fly to Massachusetts?

    The travel and health documents required for your trip to Massachusetts can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Massachusetts. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago Midway Airport to Massachusetts?


Best airlines flying from Chicago Midway Airport to Massachusetts

Compare and see reviews for airlines that fly from Chicago Midway Airport to Massachusetts with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $63Free CancellationRating
8.0
8,755 reviews
Search Delta flights
FrontierPriceFrom $86Free CancellationRating
6.1
3,536 reviews
Search Frontier flights
SouthwestPriceFrom $153Free CancellationRating
8.1
5,005 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Massachusetts?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Massachusetts from Chicago.

Can I find flights from Chicago to Massachusetts with flexible booking policies on momondo?

Yes. All flights to Massachusetts from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Massachusetts?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Massachusetts.

I’m not ready to book a flight from Chicago to Massachusetts right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Massachusetts now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Massachusetts and let you know when they change.


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