MDW - BOS

$52 Find Cheap Flights from Chicago Midway Airport to Boston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Boston departing on 1/14. 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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Search hundreds of travel sites at once for deals on flights to Boston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Boston, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Boston, as well as popular online travel agencies
In the last 7 days travelers have searched 47,946,175 times on KAYAK, and here is why:

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Cheap Flight Deals from Chicago Midway Airport to Boston (MDW-BOS)

 
These are the cheapest deals for flights from Midway to Boston currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. 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 Midway to Boston

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Boston.

Recent one-way flight deals from Midway to Boston

Only flying one-way? Below are some of the best one-way flight deals from Midway to Boston found on KAYAK recently.

Recent last minute flight deals from Midway to Boston

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Midway to Boston.

Recent direct flight deals from Midway to Boston

The latest deals for direct flights from Midway to Boston so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Midway to Boston

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

All round-trip flight deals to Boston

The cheapest plane tickets to Boston found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
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
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
$106Frontier
Find Deal
Tue, Dec 10 - Wed, Dec 11
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
8:00 am - 11:15 amMDW-BOS
2h 15mnonstop
6:40 am - 8:25 amBOS-MDW
2h 45mnonstop
$188Southwest
Find Deal
Sun, Dec 8 - Sun, Dec 15
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
3:50 pm - 10:00 pmBOS-MDW
7h 10m2 stops
$213Southwest
Find Deal
Fri, Dec 13 - Sat, Jan 4
4:58 pm - 1:22 amMDW-BOS
7h 24m1 stop
8:50 am - 5:01 pmBOS-MDW
9h 11m1 stop
$300Delta
Find Deal
Fri, Dec 6 - Tue, Dec 10
6:00 am - 12:19 pmMDW-BOS
5h 19m1 stop
8:45 am - 5:01 pmBOS-MDW
9h 16m1 stop
$315Delta
Find Deal
Tue, Dec 3 - Thu, Dec 12
6:00 am - 12:19 pmMDW-BOS
5h 19m1 stop
5:10 am - 8:58 amBOS-MDW
4h 48m1 stop
$316Delta
Find Deal
Tue, Dec 3 - Tue, Dec 10
5:24 pm - 12:30 amMDW-BOS
6h 06m1 stop
$52Frontier
Find Deal
Tue, Jan 14
5:31 pm - 12:39 amMDW-BOS
6h 08m1 stop
$53Frontier
Find Deal
Tue, Jan 21
5:24 pm - 12:30 amMDW-BOS
6h 06m1 stop
$54Frontier
Find Deal
Tue, Jan 7
2:20 pm - 12:35 amMDW-BOS
9h 15m1 stop
$59Frontier
Find Deal
Tue, Dec 17
8:40 am - 11:55 amMDW-BOS
2h 15mnonstop
$79Southwest
Find Deal
Sun, Feb 2
8:10 am - 11:25 amMDW-BOS
2h 15mnonstop
$95Southwest
Find Deal
Thu, Nov 28
6:00 am - 12:19 pmMDW-BOS
5h 19m1 stop
$158Delta
Find Deal
Tue, Dec 3
4:50 pm - 11:59 pmMDW-BOS
6h 09m1 stop
$159Delta
Find Deal
Wed, Dec 25
9:21 am - 4:54 pmMDW-BOS
30h 33m3 stops
Thu, Jan 30
9:21 am - 4:54 pmMDW-BOS
30h 33m3 stops
Sun, Feb 2
6:48 pm - 12:31 amMDW-BOS
4h 43m1 stop
12:37 pm - 7:32 pmBOS-MDW
7h 55m1 stop
$308Frontier
Find Deal
Sat, Nov 23 - Mon, Nov 25
2:41 pm - 12:59 amMDW-BOS
9h 18m1 stop
8:39 am - 5:12 pmBOS-MDW
9h 33m1 stop
$318Frontier
Find Deal
Sun, Nov 24 - Tue, Nov 26
6:48 pm - 12:31 amMDW-BOS
4h 43m1 stop
8:39 am - 5:12 pmBOS-MDW
9h 33m1 stop
$338Frontier
Find Deal
Sat, Nov 23 - Thu, Nov 28
6:00 am - 12:19 pmMDW-BOS
5h 19m1 stop
8:00 am - 1:35 pmBOS-MDW
6h 35m1 stop
$341Delta
Find Deal
Sun, Nov 24 - Wed, Nov 27
8:00 am - 11:15 amMDW-BOS
2h 15mnonstop
5:25 am - 10:20 amBOS-MDW
5h 55m1 stop
$342Southwest
Find Deal
Sun, Nov 24 - Wed, Nov 27
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
8:25 pm - 11:35 pmMDW-BOS
2h 10mnonstop
6:25 am - 8:15 amBOS-MDW
2h 50mnonstop
$348Southwest
Find Deal
Sat, Nov 23 - Tue, Nov 26
8:25 pm - 11:35 pmMDW-BOS
2h 10mnonstop
8:10 pm - 9:55 pmBOS-MDW
2h 45mnonstop
$353Southwest
Find Deal
Sat, Nov 23 - Wed, Nov 27
7:15 am - 3:05 pmMDW-BOS
6h 50m2 stops
5:25 am - 10:20 amBOS-MDW
5h 55m1 stop
$356Southwest
Find Deal
Sat, Nov 23 - Wed, Nov 27
9:30 am - 4:55 pmMDW-BOS
6h 25m1 stop
5:20 am - 8:50 amBOS-MDW
4h 30m1 stop
$391Delta
Find Deal
Fri, Nov 22 - Sun, Nov 24
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
6:40 am - 8:25 amBOS-MDW
2h 45mnonstop
$158Southwest
Find Deal
Fri, Dec 6 - Sun, Dec 8
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
6:40 am - 8:25 amBOS-MDW
2h 45mnonstop
$188Southwest
Find Deal
Sun, Dec 8 - Sun, Dec 15
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
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
6:25 am - 9:40 amMDW-BOS
2h 15mnonstop
8:00 pm - 9:45 pmBOS-MDW
2h 45mnonstop
$249Southwest
Find Deal
Thu, Dec 26 - Thu, Jan 2
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
5:10 am - 7:00 amBOS-MDW
2h 50mnonstop
$255Southwest
Find Deal
Wed, Dec 25 - Sat, Dec 28

Flights from Midway to Boston - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Boston to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Boston?

The average price of all flights from Chicago Midway Airport to Boston clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Boston on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Tuesday is the most expensive day to fly from Chicago Midway Airport to Boston. For your return ticket, we recommend flying on a Tuesday and avoiding Mondays for the best deals.

What is the cheapest month to fly from Chicago Midway Airport to Boston?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Boston, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Boston is September, where tickets cost $191 on average. On the other hand, the most expensive months are April and May, where the average cost of tickets is $298 and $284 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Boston, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Boston, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 145 days before departure.

Good to know

Low season

May

High season

October

Cheapest flight

$52
Best time to beat the crowds with an average 61% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Chicago Midway Airport to Boston

When to book flights from Midway to Boston

Are your dates flexible? Find out the best times to travel from Midway to Boston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Boston flights

  • What is the cheapest flight from Chicago Midway Airport to Boston?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Boston was $52 for a one-way ticket and $103 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Boston?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Chicago Midway Airport to Boston?

    When flying out of Chicago Midway Airport you will be using Chicago Midway. You will be landing at Boston, also known as Boston Logan Intl.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Boston?

    American Airlines, Delta, and JetBlue offer inflight Wi-Fi service on the Chicago Midway Airport to Boston flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Boston?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago Midway Airport to Boston flight route.

  • On which days can I fly direct from Chicago Midway Airport to Boston?

    There are nonstop flights from Chicago Midway Airport to Boston on a daily basis.

  • Which is the best airline for flights from Chicago to Boston, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Boston are Southwest and Delta. With an average price for the route of $270 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $422 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Boston?

    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 Chicago Midway Airport to Boston.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Boston?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Chicago Midway Airport 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 Chicago Midway Airport to Boston?

    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 Boston with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and BOS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Boston?

    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 Boston from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Boston

  • Looking for a cheap flight? 25% of our users found flights on this route for $100 or less one-way and $183 or less round-trip.

Prefer to fly non-stop from Chicago Midway Airport to Boston?

Find which airlines fly direct from Chicago Midway Airport to Boston Logan Intl Airport, which days they fly and book direct flights.

Nonstop departures

Chicago Midway to Boston Logan Intl

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Nonstop returns

Boston Logan Intl to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top 3 airlines serving from Midway to Boston

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Boston. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Boston? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.1
SouthwestOverall score based on 5015 reviews
8.2Boarding
8.1Comfort
7.2Food
7.7Entertainment
8.7Crew
Airline reviews

This was a nicer flight - not fully booked and so we were able to spread out.

10.0 ExcellentJohn, Nov 2024LAS - IND
Read more Southwest reviews

This was a nicer flight - not fully booked and so we were able to spread out.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

The last 30 min or so, they put the heat on full. We thought we were being basted.

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

Exceptional crew! Friendly and professional. Pleasant attitude and treated everyone with respect.

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Crew was nice. Flight was timely. Seats could be better as well as the food considering it’s first class.

Left on time and arrived early this extending our 31 minute transfer. Bags made it also!

Good and consistent Printer in lounge did not work for me :(

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

Bottom seat cushion is almost non existent. Very uncomfortable seat.

Delta was great the entertainment was outdated. Screen was very small and didn’t work.

My first flight was moved 6 hours causing me to miss my meeting. The second was delayed about an hour and a half. Most of the crews apparently dont like their jobs or just working for Frontier. Only one flight attendant wasn"t snappy or rude.

Booked direct in July '24. Turned into a 14 hr layover (both ways) in Denver. My 5 day vaca turned into a 1 day . Not good, BUT,... Thank you for the people @ Frontier who were professionally friendly & approachable.

Stop changing gates at sfo. When you are elderly going back for it’s not fun.

We understand and comply with Frontier’s bag sizes. We’ve had some problems in past while having to await other passengers who do not understand the baggage restrictions or have not prepaid and that is usually our biggest concern (others delaying us) with flying Frontier. Flying OUT of ONT, however, has always been a great experience. I’ve also noted even on delayed Frontier flights very knowledgeable pilots who manage expectations well.

There was no easy way to check in. I don't want to install an app to checkin. I will use alaska from now on because they have a web check in method that is easy.

The crew was ghetto lol I felt like I was on an inner city field trip

Horrible! The short distance flight ended up taking 5 hrs! There was a 3 hr delay for the flight to take off and there was a 70 min wait on the tarmac for some bogus reason that the pilot said the gate he was supposed to board was taken up. After a 30 min wait he said the plane that was supposed to push out of the gate called a medical emergency and 40 min later he ended up boarding another gate. For the initial 3 hr delay there was no information/alert about the gate or delay in the app or the boards up until the boarding time and even beyond! Had to walk all the way to the end of the terminal to find the frontier staff to ask what was going on. Avoid this airline at all costs! If you have carryon bags or checked bags , their prices come equivalent to the prices of more reliable airlines. They are the worst in timeliness at 60% (reported as delayed) this year (check the data) by a high margin even compared to the second worst airline. If you are ok with having a miserable flight experience with the odds close to flip of a coin, feel free to try them. If you value your time , money and flying experience, stay away.

There was nothing to like, flight delayed had to move to different departure areas, disorganized to say the leasr

Delayed for two hours due to trivial issues. No reimbursment. Also on arrival further delay due to terminal malfunction.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

Book cheap flights from Chicago to Boston

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Boston found on KAYAK in the last 72 hours.
1/14Tue
1 stopFrontier
6h 06mMDW-BOS
$52
1/21Tue
1 stopFrontier
6h 08mMDW-BOS
$53
1/7Tue
1 stopFrontier
6h 06mMDW-BOS
$54
12/17Tue
1 stopFrontier
9h 15mMDW-BOS
$59
2/2Sun
nonstopSouthwest
2h 15mMDW-BOS
$79
11/28Thu
nonstopSouthwest
2h 15mMDW-BOS
$95
12/3Tue
1 stopDelta
5h 19mMDW-BOS
$158
12/25Wed
1 stopDelta
6h 09mMDW-BOS
$159
1/30Thu
3 stops
30h 33mMDW-BOS
$199
2/2Sun
3 stops
30h 33mMDW-BOS
$210

Search by stops

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Last minute flights from Midway to Boston

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Boston that are departing in the next 10 days.
11/23Sat
multi-stopFrontier
4h 43mMDW-BOS
11/25Mon
multi-stopFrontier
7h 55mBOS-MDW
$308
11/24Sun
multi-stopFrontier
9h 18mMDW-BOS
11/26Tue
multi-stopFrontier
9h 33mBOS-MDW
$318
11/23Sat
multi-stopFrontier
4h 43mMDW-BOS
11/28Thu
multi-stopFrontier
9h 33mBOS-MDW
$338
11/24Sun
multi-stopDelta
5h 19mMDW-BOS
11/27Wed
multi-stopDelta
6h 35mBOS-MDW
$341
11/24Sun
nonstopSouthwest
2h 15mMDW-BOS
11/27Wed
multi-stopSouthwest
5h 55mBOS-MDW
$342
11/23Sat
multi-stopDelta
7h 03mMDW-BOS
11/27Wed
multi-stopDelta
6h 35mBOS-MDW
$346
11/23Sat
nonstopSouthwest
2h 10mMDW-BOS
11/26Tue
nonstopSouthwest
2h 50mBOS-MDW
$348
11/23Sat
nonstopSouthwest
2h 10mMDW-BOS
11/27Wed
nonstopSouthwest
2h 45mBOS-MDW
$353
11/23Sat
multi-stopSouthwest
6h 50mMDW-BOS
11/27Wed
multi-stopSouthwest
5h 55mBOS-MDW
$356
11/22Fri
multi-stopDelta
6h 25mMDW-BOS
11/24Sun
multi-stopDelta
4h 30mBOS-MDW
$391

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Everything you need to know for your flight from Midway to Boston

Information on your arrival and departure airports

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