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Cheap flights from Chicago Midway Airport to Boston from $53

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 Boston departing on 1/28. 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 Boston

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to Boston 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 Boston.

Cheap last minute flights

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

Cheap bus & train deals from Chicago Midway Airport to Boston

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

All round-trip flight deals to Boston

The cheapest plane tickets to Boston found on KAYAK recently.
4:20 pm - 12:31 amMDW-BOS
7h 11m1 stop
6:00 am - 3:12 pmBOS-MDW
10h 12m1 stop
$101Frontier
Find Deal
Wed, Feb 12 - Tue, Feb 25
5:31 pm - 12:39 amMDW-BOS
6h 08m1 stop
6:00 am - 4:16 pmBOS-MDW
11h 16m1 stop
$102Frontier
Find Deal
Tue, Feb 4 - Tue, Feb 11
5:31 pm - 12:39 amMDW-BOS
6h 08m1 stop
6:00 am - 4:16 pmBOS-MDW
11h 16m1 stop
$103Frontier
Find Deal
Tue, Feb 4 - Tue, Feb 11
5:31 pm - 12:39 amMDW-BOS
6h 08m1 stop
6:00 am - 4:16 pmBOS-MDW
11h 16m1 stop
$106Frontier
Find Deal
Tue, Feb 4 - Tue, Feb 11
6:15 am - 12:39 amMDW-BOS
17h 24m1 stop
7:00 pm - 7:32 amBOS-MDW
13h 32m1 stop
Mon, Feb 10 - Mon, Feb 17
8:40 am - 11:55 amMDW-BOS
2h 15mnonstop
7:00 am - 8:55 amBOS-MDW
2h 55mnonstop
$158Southwest
Find Deal
Sun, Jan 26 - Sun, Feb 2
4:08 pm - 12:13 amMDW-BOS
31h 05m2 stops
7:00 pm - 7:32 amBOS-MDW
13h 32m1 stop
Mon, Feb 10 - Mon, Feb 17
10:05 am - 1:20 pmMDW-BOS
2h 15mnonstop
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
$168Southwest
Find Deal
Wed, Jan 15 - Sun, Jan 19
2:08 pm - 8:04 pmMDW-BOS
4h 56m1 stop
5:35 am - 10:36 amBOS-MDW
6h 01m1 stop
$316Delta
Find Deal
Fri, Jan 17 - Sun, Jan 19
6:28 pm - 11:43 pmMDW-BOS
4h 15m1 stop
5:20 am - 8:54 amBOS-MDW
4h 34m1 stop
$321Delta
Find Deal
Thu, Jan 9 - Thu, Jan 16
5:31 pm - 12:39 amMDW-BOS
6h 08m1 stop
$53Frontier
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Tue, Jan 28
4:13 pm - 12:44 amMDW-BOS
7h 31m1 stop
$54Frontier
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Thu, Feb 27
4:20 pm - 12:31 amMDW-BOS
7h 11m1 stop
$56Frontier
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Wed, Feb 19
8:40 am - 11:55 amMDW-BOS
2h 15mnonstop
$79Southwest
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Sun, Feb 2
8:05 am - 11:20 amMDW-BOS
2h 15mnonstop
$89Southwest
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Thu, Feb 27
9:34 am - 11:42 pmMDW-BOS
13h 08m1 stop
$147Delta
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Wed, Jan 29
9:41 am - 11:38 pmMDW-BOS
12h 57m2 stops
Tue, Jan 7
6:00 am - 1:39 pmMDW-BOS
6h 39m1 stop
$158Delta
Find Deal
Sat, Jan 25
9:21 am - 4:59 pmMDW-BOS
30h 38m3 stops
Sun, Feb 2
11:08 am - 8:36 amMDW-BOS
20h 28m2 stops
$272Allegiant Air
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Sun, Apr 20
9:59 pm - 7:01 amMDW-BOS
8h 02m1 stop
5:45 am - 3:11 pmBOS-MDW
10h 26m1 stop
$278Frontier
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Mon, Dec 30 - Sat, Jan 4
6:50 am - 11:25 amMDW-BOS
27h 35m1 stop
6:00 am - 5:57 pmBOS-MDW
12h 57m1 stop
$288Frontier
Find Deal
Wed, Jan 1 - Wed, Jan 8
9:59 pm - 7:01 amMDW-BOS
8h 02m1 stop
5:45 am - 1:24 pmBOS-MDW
8h 39m1 stop
$308Frontier
Find Deal
Mon, Dec 30 - Wed, Jan 1
7:00 pm - 12:20 amMDW-BOS
4h 20m1 stop
8:15 pm - 10:00 pmBOS-MDW
2h 45mnonstop
$322Southwest
Find Deal
Mon, Dec 30 - Sat, Jan 4
10:00 am - 4:30 pmMDW-BOS
5h 30m1 stop
8:25 am - 2:00 pmBOS-MDW
6h 35m1 stop
$331Southwest
Find Deal
Tue, Dec 31 - Sat, Jan 4
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
8:15 pm - 10:00 pmBOS-MDW
2h 45mnonstop
$333Southwest
Find Deal
Tue, Dec 31 - Sat, Jan 4
8:25 pm - 11:35 pmMDW-BOS
2h 10mnonstop
8:15 pm - 10:00 pmBOS-MDW
2h 45mnonstop
$338Southwest
Find Deal
Sat, Dec 28 - Sat, Jan 4
6:25 pm - 11:51 pmMDW-BOS
4h 26m1 stop
5:35 am - 11:08 amBOS-MDW
6h 33m1 stop
$346Delta
Find Deal
Mon, Dec 30 - Sun, Jan 5
6:25 pm - 11:51 pmMDW-BOS
4h 26m1 stop
5:35 am - 11:08 amBOS-MDW
6h 33m1 stop
$366Delta
Find Deal
Mon, Dec 30 - Thu, Jan 2
6:25 pm - 11:51 pmMDW-BOS
4h 26m1 stop
12:20 pm - 4:24 pmBOS-MDW
5h 04m1 stop
$371Delta
Find Deal
Sat, Dec 28 - Sun, Jan 5
8:40 am - 11:55 amMDW-BOS
2h 15mnonstop
7:00 am - 8:55 amBOS-MDW
2h 55mnonstop
$158Southwest
Find Deal
Sun, Jan 26 - Sun, Feb 2
10:05 am - 1:20 pmMDW-BOS
2h 15mnonstop
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
$168Southwest
Find Deal
Wed, Jan 15 - Sun, Jan 19
8:35 pm - 11:50 pmMDW-BOS
2h 15mnonstop
8:05 pm - 9:55 pmBOS-MDW
2h 50mnonstop
$178Southwest
Find Deal
Thu, Mar 13 - Fri, Mar 21
10:05 am - 1:20 pmMDW-BOS
2h 15mnonstop
12:50 pm - 2:40 pmBOS-MDW
2h 50mnonstop
$188Southwest
Find Deal
Wed, Jan 15 - Sat, Jan 18
8:05 am - 11:20 amMDW-BOS
2h 15mnonstop
6:50 am - 8:45 amBOS-MDW
2h 55mnonstop
$189Southwest
Find Deal
Thu, Feb 13 - Sun, Mar 2
12:45 pm - 3:55 pmMDW-BOS
2h 10mnonstop
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
$198Southwest
Find Deal
Sat, Jan 11 - Mon, Jan 13
6:25 pm - 9:40 pmMDW-BOS
2h 15mnonstop
6:35 pm - 8:25 pmBOS-MDW
2h 50mnonstop
$208Southwest
Find Deal
Tue, Feb 11 - Tue, Feb 18
8:40 am - 11:55 amMDW-BOS
2h 15mnonstop
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
$218Southwest
Find Deal
Thu, Jan 16 - Sun, Jan 19
12:45 pm - 3:55 pmMDW-BOS
2h 10mnonstop
6:35 pm - 8:25 pmBOS-MDW
2h 50mnonstop
$238Southwest
Find Deal
Sat, Jan 25 - Sun, Jan 26
8:20 pm - 11:35 pmMDW-BOS
2h 15mnonstop
7:45 pm - 9:35 pmBOS-MDW
2h 50mnonstop
$239Southwest
Find Deal
Fri, Feb 14 - Sun, Feb 16

Frontier flights from Chicago Midway Airport to Boston

Our best Frontier deals on Chicago Midway Airport to Boston flight tickets
Frontier
Feb 12
MDW4:20 pmChicago Midway
7h 11m
1 stop
BOS12:31 amBoston Logan Intl
Feb 25
BOS6:00 amBoston Logan Intl
10h 12m
1 stop
MDW3:12 pmChicago Midway
Frontier
Feb 4
MDW5:31 pmChicago Midway
6h 08m
1 stop
BOS12:39 amBoston Logan Intl
Feb 11
BOS6:00 amBoston Logan Intl
11h 16m
1 stop
MDW4:16 pmChicago Midway
Frontier
Feb 4
MDW5:31 pmChicago Midway
6h 08m
1 stop
BOS12:39 amBoston Logan Intl
Feb 11
BOS6:00 amBoston Logan Intl
11h 16m
1 stop
MDW4:16 pmChicago Midway

Southwest flights from Chicago Midway Airport to Boston

Our best Southwest deals on Chicago Midway Airport to Boston flight tickets
Southwest
Jan 26
MDW8:40 amChicago Midway
2h 15m
BOS11:55 amBoston Logan Intl
Feb 2
BOS7:00 amBoston Logan Intl
2h 55m
MDW8:55 amChicago Midway
Southwest
Jan 15
MDW10:05 amChicago Midway
2h 15m
BOS1:20 pmBoston Logan Intl
Jan 19
BOS8:10 amBoston Logan Intl
2h 55m
MDW10:05 amChicago Midway
Southwest
Jan 15
MDW10:05 amChicago Midway
2h 15m
BOS1:20 pmBoston Logan Intl
Jan 18
BOS12:50 pmBoston Logan Intl
2h 50m
MDW2:40 pmChicago Midway

See travel insights to Boston from

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

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 Boston?

In general, September is the cheapest month to fly from Chicago Midway Airport to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $191. If you aren’t able to travel during the month of September, then book flights to Boston from Chicago Midway Airport during January instead. Flights to Boston in January, while not as cheap as those in September, still average around $197.

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

The cheapest day to depart from Chicago Midway Airport to Boston is on a Wednesday when prices can be found for as low as $222. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Sunday is $297.

What is the cheapest time of day to depart on your flight to Boston?

According to our data, the cheapest time of day to fly to Boston is in the evening. momondo users have found flights departing from Chicago Midway Airport to Boston in the evening for as low as $205. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. At noon is when there is more demand to fly to Boston, so prices are often more expensive at around $257 per ticket.

What is the cheapest Chicago Midway to Boston Logan Intl flight route?

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

What cabin class options are available on Chicago Midway to Boston Logan Intl flights?

There are 1 cabin classes available to choose from on Chicago Midway to Boston Logan Intl 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 Boston flights?

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

How have Chicago Midway Airport to Boston flight prices changed over time?

As of December 2024, prices for Chicago Midway Airport to Boston flights are approximately 9% cheaper when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to Boston

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Boston according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Boston (MDW to BOS) flight deals and tips

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

Best Price Found

$53

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Boston

1 airport
The best one-way flight to Boston from Chicago Midway Airport in the past 72 hours is $53. The best round-trip flight deal from Chicago Midway Airport to Boston found on momondo in the last 72 hours is $101.
The fastest flight from Chicago Midway Airport to Boston takes 2h 10m
Direct flights go from Chicago Midway Airport to Boston every day.
There is 1 airport near Boston: Boston Logan Intl (BOS)

  • How far is Chicago Midway to Boston Logan Intl by plane?

    Chicago Midway and Boston Logan Intl are 854.8 mi apart from one another. Typically, this will take 2h 10m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to Boston Logan Intl Airport?

    Prices for flights from Chicago Midway Airport to Boston Logan Intl Airport were last updated today.

  • How many operators does momondo search for flights from Chicago Midway Airport to Boston Logan Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Boston Logan Intl Airport?

    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 Boston Logan Intl Airport.

  • What documentation or ID do you need to fly to Boston Logan Intl Airport?

    The required travel and health documents for your Boston Logan Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Boston Logan Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

  • What is the most popular airline from Chicago Midway Airport to Boston?


Best airlines flying from Chicago Midway Airport to Boston

Compare and see reviews for airlines that fly from Chicago Midway Airport to Boston with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $63Free CancellationRating
8.0
8,556 reviews
Search Delta flights
FrontierPriceFrom $86Free CancellationRating
6.0
3,459 reviews
Search Frontier flights
SouthwestPriceFrom $153Free CancellationRating
8.1
4,731 reviews
Search Southwest flights
United AirlinesPriceFrom $157Free CancellationRating
7.4
9,003 reviews
Search United Airlines flights
  • Southwest Flights From Chicago Midway Airport to Boston

    Southwest flight deals from Chicago Midway Airport to Boston start from $153 round-trip. Over the 20 Southwest flights for this route in a normal week, average airfare is usually $276 round-trip - but some users have found much cheaper deals with momondo.


Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Boston for you.

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

momondo does allow users to show only those flights to Boston from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search for Chicago to Boston flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Of course. momondo tracks the price of Chicago to Boston flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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