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Cheap flights from Massachusetts to Chicago Midway Airport from $50

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Chicago Midway Airport departing on 12/18. 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 Massachusetts to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Massachusetts to Chicago 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 Massachusetts to Chicago.

Cheap last minute flights

Planning a quick getaway from Massachusetts to Chicago? 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 Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Massachusetts to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
6:00 am - 4:14 pmBOS-MDW
11h 14m1 stop
5:31 pm - 12:39 amMDW-BOS
6h 08m1 stop
$103Frontier
Find Deal
Tue, Jan 14 - Tue, Jan 21
6:00 am - 5:57 pmBOS-MDW
12h 57m1 stop
5:31 pm - 12:39 amMDW-BOS
6h 08m1 stop
$106Frontier
Find Deal
Wed, Jan 15 - Tue, Jan 28
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
5:24 pm - 12:30 amMDW-BOS
6h 06m1 stop
$108Frontier
Find Deal
Wed, Dec 11 - Tue, Jan 14
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
$114Frontier
Find Deal
Tue, Dec 10 - Wed, Dec 11
6:40 am - 8:25 amBOS-MDW
2h 45mnonstop
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
$158Southwest
Find Deal
Fri, Dec 13 - Mon, Dec 16
5:05 am - 6:55 amBOS-MDW
2h 50mnonstop
1:15 pm - 4:25 pmMDW-BOS
2h 10mnonstop
$178Southwest
Find Deal
Sat, Dec 14 - Sat, Dec 14
11:55 am - 11:20 pmBOS-MDW
12h 25m1 stop
6:50 am - 8:50 pmMDW-BOS
37h 00m2 stops
Mon, Dec 30 - Wed, Jan 1
5:45 am - 8:50 amALB-MDW
4h 05m1 stop
6:25 pm - 11:20 pmMDW-ALB
3h 55m1 stop
$303Delta
Find Deal
Wed, Dec 25 - Sun, Dec 29
1:03 pm - 5:02 pmBOS-MDW
4h 59m1 stop
9:30 am - 3:50 pmMDW-BOS
5h 20m1 stop
$310Delta
Find Deal
Thu, Dec 5 - Mon, Dec 9
7:50 am - 6:32 pmBDL-MDW
35h 42m3 stops
5:35 pm - 10:02 pmMDW-BDL
27h 27m3 stops
Thu, Dec 12 - Sun, Dec 15
5:45 am - 1:24 pmBOS-MDW
8h 39m1 stop
$50Frontier
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Wed, Dec 18
6:00 am - 7:06 pmBOS-MDW
14h 06m1 stop
$56Frontier
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Wed, Jan 29
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
$79Southwest
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Mon, Jan 27
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
$89Southwest
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Tue, Feb 25
7:01 pm - 8:31 amALB-MDW
14h 30m1 stop
$115Allegiant Air
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Sat, Jan 11
9:34 am - 8:41 amBOS-MDW
24h 07m2 stops
Mon, Jan 6
5:45 am - 8:50 amALB-MDW
4h 05m1 stop
$139Delta
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Wed, Dec 25
6:51 pm - 8:31 amALB-MDW
14h 40m1 stop
$146Allegiant Air
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Sat, Feb 1
11:15 am - 6:32 pmBOS-MDW
8h 17m1 stop
$156Delta
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Tue, Dec 3
9:34 am - 8:41 amBOS-MDW
24h 07m2 stops
Mon, Dec 30
8:35 am - 2:50 pmBOS-MDW
7h 15m1 stop
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
$292Southwest
Find Deal
Wed, Nov 27 - Wed, Dec 4
3:15 pm - 5:00 pmBOS-MDW
2h 45mnonstop
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
$303Southwest
Find Deal
Wed, Nov 27 - Wed, Dec 4
5:45 pm - 11:15 pmBOS-MDW
6h 30m1 stop
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
$310Southwest
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Wed, Nov 27 - Wed, Dec 4
3:05 pm - 9:40 pmBOS-MDW
7h 35m2 stops
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
$317Southwest
Find Deal
Wed, Nov 27 - Wed, Dec 4
8:10 pm - 9:55 pmBOS-MDW
2h 45mnonstop
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
$321Southwest
Find Deal
Wed, Nov 27 - Wed, Dec 4
11:35 am - 9:59 pmBOS-MDW
11h 24m1 stop
6:07 pm - 7:49 amMDW-BOS
12h 42m1 stop
$325Frontier
Find Deal
Tue, Nov 26 - Thu, Nov 28
3:10 pm - 9:46 pmBOS-MDW
7h 36m1 stop
1:30 pm - 8:00 pmMDW-BOS
5h 30m1 stop
$339Delta
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Thu, Nov 28 - Tue, Dec 3
5:20 am - 8:50 amBOS-MDW
4h 30m1 stop
9:31 am - 3:50 pmMDW-BOS
5h 19m1 stop
$364Delta
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Tue, Nov 26 - Tue, Dec 3
2:12 pm - 11:15 pmBDL-MDW
10h 03m1 stop
7:42 am - 6:16 pmMDW-BDL
9h 34m1 stop
$398Frontier
Find Deal
Thu, Nov 28 - Mon, Dec 2
8:00 am - 10:20 amBDL-MDW
27h 20m3 stops
8:15 pm - 5:00 pmMDW-BDL
19h 45m2 stops
Thu, Nov 28 - Sun, Dec 1
6:40 am - 8:25 amBOS-MDW
2h 45mnonstop
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
$158Southwest
Find Deal
Fri, Dec 13 - Mon, Dec 16
5:05 am - 6:55 amBOS-MDW
2h 50mnonstop
1:15 pm - 4:25 pmMDW-BOS
2h 10mnonstop
$178Southwest
Find Deal
Sat, Dec 14 - Sat, Dec 14
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
7:00 pm - 10:15 pmMDW-BOS
2h 15mnonstop
$188Southwest
Find Deal
Wed, Jan 8 - Sun, Jan 12
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
$192Southwest
Find Deal
Mon, Dec 9 - Thu, Dec 12
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
6:20 am - 9:35 amMDW-BOS
2h 15mnonstop
$195Southwest
Find Deal
Wed, Jan 1 - Sat, Jan 4
6:40 am - 8:25 amBOS-MDW
2h 45mnonstop
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
$200Southwest
Find Deal
Fri, Jan 3 - Mon, Jan 6
6:35 pm - 8:25 pmBOS-MDW
2h 50mnonstop
7:00 pm - 10:15 pmMDW-BOS
2h 15mnonstop
$218Southwest
Find Deal
Thu, Jan 16 - Mon, Jan 20
6:25 am - 8:15 amBOS-MDW
2h 50mnonstop
8:25 pm - 11:35 pmMDW-BOS
2h 10mnonstop
$220Southwest
Find Deal
Mon, Dec 30 - Sun, Jan 5
7:45 pm - 9:35 pmBOS-MDW
2h 50mnonstop
8:40 am - 11:55 amMDW-BOS
2h 15mnonstop
$230Southwest
Find Deal
Fri, Feb 21 - Mon, Feb 24
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
$236Southwest
Find Deal
Thu, Dec 5 - Fri, Dec 6

Delta flights from Massachusetts to Chicago Midway Airport

Our best Delta deals on Massachusetts to Chicago Midway Airport flight tickets
Delta
Dec 25
ALB5:45 amAlbany Intl
4h 05m
1 stop
MDW8:50 amChicago Midway
Dec 29
MDW6:25 pmChicago Midway
3h 55m
1 stop
ALB11:20 pmAlbany Intl
Delta
Dec 5
BOS1:03 pmBoston Logan Intl
4h 59m
1 stop
MDW5:02 pmChicago Midway
Dec 9
MDW5:50 pmChicago Midway
4h 57m
1 stop
BOS11:47 pmBoston Logan Intl
Delta
Dec 5
BOS1:03 pmBoston Logan Intl
4h 59m
1 stop
MDW5:02 pmChicago Midway
Dec 9
MDW5:50 pmChicago Midway
4h 57m
1 stop
BOS11:47 pmBoston Logan Intl

Frontier flights from Massachusetts to Chicago Midway Airport

Our best Frontier deals on Massachusetts to Chicago Midway Airport flight tickets
Frontier
Jan 14
BOS6:00 amBoston Logan Intl
11h 14m
1 stop
MDW4:14 pmChicago Midway
Jan 21
MDW5:31 pmChicago Midway
6h 08m
1 stop
BOS12:39 amBoston Logan Intl
Frontier
Jan 15
BOS6:00 amBoston Logan Intl
12h 57m
1 stop
MDW5:57 pmChicago Midway
Jan 28
MDW5:31 pmChicago Midway
6h 08m
1 stop
BOS12:39 amBoston Logan Intl
Frontier
Dec 11
BOS6:00 amBoston Logan Intl
6h 42m
1 stop
MDW11:42 amChicago Midway
Jan 14
MDW5:24 pmChicago Midway
6h 06m
1 stop
BOS12:30 amBoston Logan Intl

See travel insights to Chicago from

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

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 month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Massachusetts, with most prices found around $188. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Massachusetts during the month December is also very affordable. Most momondo users find prices during this month for around $188.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Massachusetts. The lowest ticket price found for a Tuesday departure recently was $213. 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, Monday is the most expensive day to depart from Massachusetts because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $368.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Massachusetts in the morning is the least expensive time of day to depart. momondo users have found prices as low as $248 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $305. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Massachusetts to Chicago Midway flight route?

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

How far in advance should I book a flight to Chicago Midway Airport?

We recommend purchasing flights from Massachusetts to Chicago Midway Airport 45 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to Chicago Midway Airport for $301. In the past 72 hours, momondo users found flights from Massachusetts to Chicago Midway Airport for as low as $128.

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

There are 1 cabin classes available to choose from on Massachusetts to Chicago Midway 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 Massachusetts to Chicago Midway Airport flights?

You could potentially save up to 29% on your flight if you consider stops on a Massachusetts to Chicago Midway Airport flight.

Cheap Massachusetts to Chicago Midway Airport flight deals and tips

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

Best Price Found

$50

Fastest flight time

2h 15m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Massachusetts in the past 72 hours is $50. The best round-trip flight deal from Massachusetts to Chicago Midway Airport found on momondo in the last 72 hours is $103.
The fastest flight from Massachusetts to Chicago Midway Airport takes 2h 15m
Direct flights go from Massachusetts to Chicago Midway Airport every day.

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

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

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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


Best airlines flying from Massachusetts to Chicago Midway Airport

Compare and see reviews for airlines that fly from Massachusetts to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $76Free CancellationRating
6.3
8,176 reviews
Search Spirit Airlines flights
FrontierPriceFrom $100Free CancellationRating
6.1
3,526 reviews
Search Frontier flights
United AirlinesPriceFrom $147Free CancellationRating
7.4
9,156 reviews
Search United Airlines flights
SouthwestPriceFrom $148Free CancellationRating
8.1
4,984 reviews
Search Southwest flights
DeltaPriceFrom $315Free CancellationRating
8.0
8,734 reviews
Search Delta flights

Why use momondo?

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

It is quick and easy to find Massachusetts to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

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

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

momondo helps you find the best flight between Massachusetts and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Price alerts on flights to Chicago from Massachusetts are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


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