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MDW - BOS

$75 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 7/24. 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
Tue 7/9
Tue 7/16

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 42,898,604 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
2:29 pm - 12:27 amMDW-BOS
8h 58m1 stop
12:36 pm - 7:13 pmBOS-MDW
7h 37m1 stop
$124Frontier
Find Deal
Wed, Aug 7 - Wed, Aug 14
2:29 pm - 12:27 amMDW-BOS
8h 58m1 stop
6:00 am - 1:28 pmBOS-MDW
8h 28m1 stop
$125Frontier
Find Deal
Wed, Aug 7 - Mon, Aug 12
10:16 pm - 6:58 amMDW-BOS
7h 42m1 stop
9:18 am - 10:58 pmBOS-MDW
14h 40m1 stop
$126Frontier
Find Deal
Tue, Jun 18 - Wed, Jun 19
10:16 pm - 6:58 amMDW-BOS
7h 42m1 stop
6:00 am - 1:34 pmBOS-MDW
8h 34m1 stop
$127Frontier
Find Deal
Tue, Jun 25 - Wed, Jul 24
10:16 pm - 6:58 amMDW-BOS
7h 42m1 stop
9:18 am - 10:58 pmBOS-MDW
14h 40m1 stop
$128Frontier
Find Deal
Tue, Jun 18 - Wed, Jun 19
12:07 pm - 7:49 pmMDW-BOS
6h 42m1 stop
5:20 am - 8:48 amBOS-MDW
4h 28m1 stop
$314Delta
Find Deal
Sat, Jun 15 - Sun, Jun 16
5:45 pm - 11:59 pmMDW-BOS
5h 14m1 stop
5:50 am - 11:28 amBOS-MDW
6h 38m1 stop
$316Delta
Find Deal
Wed, Jul 3 - Sat, Jul 6
9:08 pm - 8:23 amMDW-BOS
10h 15m1 stop
6:00 am - 8:18 pmBOS-MDW
15h 18m3 stops
Fri, Jun 28 - Mon, Jul 1
9:08 pm - 8:23 amMDW-BOS
10h 15m1 stop
9:41 pm - 8:18 pmBOS-MDW
23h 37m3 stops
Fri, Jun 14 - Thu, Jun 27
5:15 pm - 8:57 amMDW-BOS
14h 42m1 stop
12:50 pm - 9:37 pmBOS-MDW
9h 47m1 stop
$492Porter Airlines
Find Deal
Wed, Jun 26 - Sun, Jun 30

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 $313 and $307 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 $124 on Frontier, followed by Delta ($314). One-way flight deals have also been found from as low as $75 on Frontier and from $118 on Allegiant Air.

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

Each day, there are between 4 and 8 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 12:00 pm and most flights take off in the morning. Each week, there are 41 flights. The most frequent day of departure is Friday, when 20% 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.

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

$75
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 70% 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 $75 for a one-way ticket and $124 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 10310 reviews
8.6Crew
8.0Entertainment
7.9Comfort
8.2Boarding
7.4Food
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

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

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

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.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

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.

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.
7/24Wed
1 stopFrontier
8h 58mMDW-BOS
$75
7/10Wed
1 stopFrontier
8h 58mMDW-BOS
$76
6/21Fri
1 stopAllegiant Air
10h 15mMDW-BOS
$118
7/1Mon
1 stopAllegiant Air
10h 15mMDW-BOS
$121
7/1Mon
2 stops
16h 17mMDW-BOS
$150
7/30Tue
1 stopDelta
6h 54mMDW-BOS
$158
6/12Wed
1 stopDelta
5h 22mMDW-BOS
$178
7/8Mon
3 stops
27h 14mMDW-BOS
$180
6/13Thu
2 stopsSouthwest
8h 25mMDW-BOS
$188
6/13Thu
3 stopsSouthwest
9h 35mMDW-BOS
$270

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.
6/14Fri
multi-stopFrontier
13h 58mMDW-BOS
6/19Wed
multi-stopFrontier
6h 43mBOS-MDW
$145
6/14Fri
multi-stopFrontier
13h 58mMDW-BOS
6/18Tue
multi-stopFrontier
9h 38mBOS-MDW
$158
6/11Tue
multi-stopFrontier
7h 42mMDW-BOS
6/19Wed
multi-stopFrontier
14h 40mBOS-MDW
$159
6/14Fri
multi-stopFrontier
13h 58mMDW-BOS
6/18Tue
multi-stopFrontier
9h 38mBOS-MDW
$162
6/12Wed
multi-stopDelta
5h 22mMDW-BOS
6/18Tue
multi-stopDelta
4h 28mBOS-MDW
$334
6/12Wed
multi-stopDelta
5h 38mMDW-BOS
6/16Sun
multi-stopDelta
4h 28mBOS-MDW
$336
6/14Fri
multi-stop
10h 15mMDW-BOS
6/27Thu
multi-stop
23h 37mBOS-MDW
$426
6/14Fri
multi-stop
10h 15mMDW-BOS
6/24Mon
multi-stop
6h 42mBOS-MDW
$549
6/12Wed
multi-stopPorter Airlines
7h 22mMDW-BOS
6/21Fri
multi-stopPorter Airlines
16h 17mBOS-MDW
$833
6/13Thu
multi-stopPorter Airlines
6h 07mMDW-BOS
6/17Mon
multi-stopPorter Airlines
12h 52mBOS-MDW
$1,008

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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