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MDW - BOS

$64 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 8/21. 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
0 bags
Mon 7/1
Mon 7/8

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 42,787,818 times on KAYAK, and here is why:

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Cheap flight deals from Midway to Boston (MDW-BOS)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Boston 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 and deals for you by selecting your travel dates.
Choose your dates
7:59 pm - 7:25 amMDW-BOS
10h 26m1 stop
10:10 am - 7:13 pmBOS-MDW
10h 03m1 stop
$116Frontier
Find Deal
Wed, Aug 28 - Sat, Aug 31
10:16 pm - 6:58 amMDW-BOS
7h 42m1 stop
9:16 am - 9:31 amBOS-MDW
25h 15m1 stop
$120Frontier
Find Deal
Tue, Jun 11 - Wed, Jun 12
7:59 pm - 7:25 amMDW-BOS
10h 26m1 stop
12:36 pm - 7:13 pmBOS-MDW
7h 37m1 stop
$124Frontier
Find Deal
Tue, Aug 13 - Tue, Aug 20
7:59 pm - 7:25 amMDW-BOS
10h 26m1 stop
12:36 pm - 7:13 pmBOS-MDW
7h 37m1 stop
$126Frontier
Find Deal
Wed, Aug 14 - Tue, Aug 20
6:15 pm - 9:30 pmMDW-BOS
2h 15mnonstop
6:30 am - 8:05 amBOS-MDW
2h 35mnonstop
$246Southwest
Find Deal
Tue, Jun 11 - Fri, Jun 14
5:15 pm - 11:45 pmMDW-BOS
5h 30m1 stop
6:30 am - 8:05 amBOS-MDW
2h 35mnonstop
$255Southwest
Find Deal
Tue, Jun 11 - Fri, Jun 14
9:34 am - 3:56 pmMDW-BOS
5h 22m1 stop
5:20 am - 8:48 amBOS-MDW
4h 28m1 stop
$314Delta
Find Deal
Tue, Jun 11 - Sat, Jun 15
5:45 pm - 11:56 pmMDW-BOS
5h 11m1 stop
5:20 am - 8:49 amBOS-MDW
4h 29m1 stop
$316Delta
Find Deal
Sat, Jun 29 - Mon, Jul 1
9:08 pm - 8:23 amMDW-BOS
10h 15m1 stop
8:00 pm - 7:00 pmBOS-MDW
24h 00m3 stops
Fri, Jun 21 - Thu, Jun 27
9:08 pm - 8:23 amMDW-BOS
10h 15m1 stop
7:46 pm - 7:00 pmBOS-MDW
24h 14m2 stops
Fri, Jun 21 - Thu, Jun 27

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, Sunday 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 Saturdays 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 January, where tickets cost $201 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $316 and $308 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 84 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to Boston?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago Midway Airport to Boston found by KAYAK users in the last 72 hours was for $116 on Frontier, followed by Southwest ($246). One-way flight deals have also been found from as low as $64 on Frontier and from $108 on Allegiant Air.

How many flights are there between Chicago Midway Airport and Boston per day?

Each day, there are between 4 and 6 nonstop flights that take off from Chicago Midway Airport and land in Boston, with an average flight time of 2h 15m. The most common departure time is 1:00 pm and most flights take off in the morning. Each week, there are 39 flights. The most frequent day of departure is Wednesday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Chicago Midway Airport and Boston?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago Midway Airport to Boston take?

Direct flights take on average 2h 15m to travel the 857 miles between Chicago Midway Airport and Boston.

What’s the earliest departure time from Chicago Midway Airport to Boston?

Early birds can take the earliest flight from Chicago Midway Airport at 6:00 am and will be landing in Boston at 9:15 am.

What’s the latest departure time from Chicago Midway Airport to Boston?

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Boston jets off at 9:15 pm and lands at 12:30 am.

Good to know

Low season

February

High season

May

Cheapest flight

$64
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 71% lower on average.
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 $64 for a one-way ticket and $116 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, JetBlue, and Delta 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 Embraer 175 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, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to Boston are Delta and Frontier. With an average price for the route of $409 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $168 and an overall rating of 6.2.

  • 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

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

Find which airlines fly direct from Midway to Logan Intl, 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.
8.0
DeltaOverall score based on 10419 reviews
7.9Comfort
8.2Boarding
8.0Entertainment
7.4Food
8.6Crew
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The boarding was horrible. You couldn’t hear the announcements at all. Probably because there is so much in the area for businesses. They need a louder PA system. Other than that it was a good Delta experience.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Terrible. Delta delays caused us to miss our flight and they did nothing to fix it.

The A330-200 was showing its age but otherwise this was a pleasant flight with friendly crew. The meals/snack provided were pretty good.

The most unprofessional and disorganized experience I’ve ever had with an airlines. After the flight was diverted on the runway and we returned to the gate, there was no communication about the plans and it took an additional 5 hours to get set up with a hotel and a new flight, information that was not readily given to the passengers and mostly gotten second hand from what other passengers heard from each other. Based on this experience I cannot recommend flying delta again

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Crew was great and did their best to make us comfortable and captain came out at the beginning to announce why the flight was delayed, weather situation up ahead, and kept us updated throughout the flight.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

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.
8/21Wed
1 stopFrontier
10h 26mMDW-BOS
$64
6/11Tue
1 stopFrontier
7h 42mMDW-BOS
$67
6/21Fri
1 stopAllegiant Air
10h 15mMDW-BOS
$108
9/20Fri
1 stopAllegiant Air
15h 31mMDW-BOS
$117
7/1Mon
2 stops
16h 17mMDW-BOS
$137
6/24Mon
2 stops
16h 17mMDW-BOS
$139
6/19Wed
1 stopDelta
5h 25mMDW-BOS
$158
6/19Wed
1 stopDelta
5h 25mMDW-BOS
$164
7/14Sun
2 stopsPorter Airlines
8h 50mMDW-BOS
$267
6/21Fri
2 stopsPorter Airlines
9h 05mMDW-BOS
$268

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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.
6/6Thu
multi-stopFrontier
10h 25mMDW-BOS
6/10Mon
multi-stopFrontier
6h 49mBOS-MDW
$126
6/6Thu
multi-stopFrontier
10h 25mMDW-BOS
6/12Wed
multi-stopFrontier
6h 43mBOS-MDW
$148
6/3Mon
multi-stopDelta
4h 41mMDW-BOS
6/6Thu
multi-stopDelta
4h 31mBOS-MDW
$335
6/4Tue
multi-stopDelta
7h 13mMDW-BOS
6/8Sat
multi-stopDelta
4h 57mBOS-MDW
$344
6/3Mon
multi-stopSouthwest
11h 15mMDW-BOS
6/6Thu
nonstopSouthwest
2h 35mBOS-MDW
$378
6/2Sun
multi-stopSouthwest
5h 20mMDW-BOS
6/6Thu
nonstopSouthwest
2h 35mBOS-MDW
$382
6/5Wed
multi-stopPorter Airlines
14h 42mMDW-BOS
6/18Tue
multi-stopPorter Airlines
19h 12mBOS-MDW
$775
6/5Wed
multi-stopPorter Airlines
16h 20mMDW-BOS
6/18Tue
multi-stopPorter Airlines
19h 12mBOS-MDW
$785
6/5Wed
multi-stop
16h 20mMDW-BOS
6/18Tue
multi-stop
24h 26mBOS-MDW
$814
6/6Thu
multi-stop
14h 42mMDW-BOS
6/9Sun
multi-stop
21h 48mBOS-MDW
$1,304

Search by stops

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Chicago Midway Airport - Boston Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Boston (BOS)United States

Return flight deals:

Boston - Chicago Midway Airport

Cabin classes:

$369