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BOS - MDW

$49 Find cheap flights from Boston to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Midway departing on 8/14. 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.
1 adult
0 bags
Wed 7/10
Wed 7/17

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Chicago, 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 Boston to Chicago, 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:

Save 21% or moreCompare multiple travel sites with one search.

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Filter your dealsChoose cabin class, free Wi-Fi and more.

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Midway 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
12:36 pm - 7:13 pmBOS-MDW
7h 37m1 stop
7:59 pm - 7:25 amMDW-BOS
10h 26m1 stop
$96Frontier
Find Deal
Wed, Aug 14 - Wed, Aug 21
12:48 pm - 7:13 pmBOS-MDW
7h 25m1 stop
7:59 pm - 7:25 amMDW-BOS
10h 26m1 stop
$100Frontier
Find Deal
Sat, Aug 17 - Tue, Aug 20
9:16 am - 9:55 pmBOS-MDW
13h 39m1 stop
7:59 pm - 7:25 amMDW-BOS
10h 26m1 stop
$102Frontier
Find Deal
Fri, Aug 16 - Tue, Aug 20
12:36 pm - 7:13 pmBOS-MDW
7h 37m1 stop
12:15 pm - 9:20 amMDW-BOS
20h 05m1 stop
$104Frontier
Find Deal
Wed, Aug 14 - Fri, Aug 16
12:36 pm - 7:13 pmBOS-MDW
7h 37m1 stop
7:59 pm - 7:25 amMDW-BOS
10h 26m1 stop
$114Frontier
Find Deal
Thu, Aug 15 - Mon, Aug 19
5:20 am - 8:49 amBOS-MDW
4h 29m1 stop
9:33 am - 3:54 pmMDW-BOS
5h 21m1 stop
$316Delta
Find Deal
Tue, Jul 2 - Tue, Jul 23
5:20 am - 8:38 amBOS-MDW
4h 18m1 stop
9:33 am - 3:54 pmMDW-BOS
5h 21m1 stop
$360Delta
Find Deal
Sat, Jul 13 - Tue, Jul 16
9:15 am - 12:43 pmBOS-MDW
4h 28m1 stop
5:45 pm - 11:56 pmMDW-BOS
5h 11m1 stop
$366Delta
Find Deal
Thu, Jun 20 - Sat, Jun 22
6:50 am - 8:17 pmBOS-MDW
14h 27m3 stops
8:30 pm - 8:17 amMDW-BOS
10h 47m1 stop
Mon, Jul 22 - Fri, Jul 26
5:20 am - 8:38 amBOS-MDW
4h 18m1 stop
6:55 pm - 1:03 amMDW-BOS
5h 08m1 stop
$404Delta
Find Deal
Sat, Jul 13 - Mon, Jul 15

Flights from Boston to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from Boston to Midway 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 Boston to Chicago Midway Airport?

The average price of all flights from Boston to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Boston to Chicago Midway Airport, look for departures on Tuesdays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Wednesday is the cheapest day to fly and Sunday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Boston to Chicago Midway Airport, 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 Boston to Chicago Midway Airport is December, where tickets cost $199 on average. On the other hand, the most expensive months are June and October, where the average cost of tickets is $439 and $436 respectively.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Boston to Chicago Midway Airport found by KAYAK users in the last 72 hours was for $96 on Frontier, followed by Delta ($316). One-way flight deals have also been found from as low as $49 on Frontier and from $126 on Allegiant Air.

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

Each day, there are between 4 and 10 nonstop flights that take off from Boston and land in Chicago Midway Airport, with an average flight time of 2h 39m. The most common departure time is 4:00 pm and most flights take off in the afternoon. Each week, there are 50 flights. The most frequent day of departure is Thursday, when 20% of all weekly flights depart. The fewest flights depart on a Saturday.

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

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 Boston to Chicago Midway Airport?

Early birds can take the earliest flight from Boston at 5:45 am and will be landing in Chicago Midway Airport at 7:20 am.

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

If you prefer to fly at night, the latest flight from Boston to Chicago Midway Airport jets off at 8:15 pm and lands at 9:55 pm.

Good to know

Low season

January

High season

April

Cheapest flight

$49
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from Boston to Chicago Midway Airport

When to book flights from Boston to Midway

Are your dates flexible? Find out the best times to travel from Boston to Midway 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 Boston to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Boston to Chicago Midway Airport was $49 for a one-way ticket and $96 for a round-trip.

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

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

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

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

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

    The Boeing 737-700 Passenger/BBJ1 (winglets) is the aircraft model that flies most regularly on the Boston to Chicago Midway Airport flight route.

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

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

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

    The two airlines most popular with KAYAK users for flights from Boston to Chicago are Delta and Frontier. With an average price for the route of $461 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 $156 and an overall rating of 6.2.

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

    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 Boston to Chicago Midway Airport.

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

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

    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 Chicago Midway Airport with an airline and back to Boston with another airline. Booking your flights between Boston and MDW 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 Boston to Chicago Midway Airport?

    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 Chicago Midway Airport from Boston 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 Boston to Chicago Midway Airport?

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

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top 4 airlines serving from Boston to Midway

 
See real verified KAYAK customer reviews for airlines flying from Boston to Chicago. 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 Boston to Midway? 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 10295 reviews
7.9Comfort
8.0Entertainment
7.4Food
8.2Boarding
8.6Crew
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.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

They did a fine job. Can't wait to use Delta in the future.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Seats in first class on the E175 recline too far back. I was in 2A, and the man in 1A fully reclined almost the entire flight. It took 6-7 inches of space away from me and made it very difficult to work on my laptop.

Mario was great. Made a night flight on a small aircraft pleasant and memorable.

Crew were exceptional. Plane was quiet and quite empty, so I had a row to sleep across.

The seat could use more support or cushion. I'm in my 50's and have back issues so the seats are a bit hard for longer flights.

The plane was in bad condition. We were taxied for mode than an hour because a light panel had feel off. The bathroom in first class had broken panels as well. Overall poor aircraft maintenance

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

No lounge access with “United First” ticket. False alarm about late flight, jeopardizing connection. Wrong meal. Loose power socket would not hold plug, could not charge device. In-flight access to text messaging did not work. Toilet seat on plane would not stay up.

Our original business class flight was cancelled so we not only downgraded but we were also spread out across the plane not sitting together in separate middle seats. My poor kids were scared and couldn’t see me on the flight and the crew wasn’t sensitive to the situation and what the airlines did to us. Very dissatisfied with United airlines.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Worst experience flying American Airlines. I fly with them often, so I was super disappointed in the service I received at gate 30 in LGA on May 24, mid-day. The flight was delayed twice. I was patiently waiting in the American Airlines lounge when I received the notice on my app that the plane was boarding 45 minutes before its newly re-scheduled take off of 4 pm (from the orginal 1:45 pm then 3:00 pm). It took me 5 min to travel from the lounge to the gate and when I arrived there at 3:20 flight gate attendant told me the flight had closed and that they announced for passengers multiple times. I showed them the notification on my app and they were really rude and unempathetic. The person who rescheduled my flight at customer service wasn't any happier but was at least helpful in getting me on the next flight.

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

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 Boston to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Boston to Chicago found on KAYAK in the last 72 hours.
8/14Wed
1 stopFrontier
7h 37mBOS-MDW
$49
8/13Tue
1 stopFrontier
7h 37mBOS-MDW
$50
8/16Fri
1 stopAllegiant Air
7h 23mBOS-MDW
$126
10/4Fri
1 stopAllegiant Air
10h 38mBOS-MDW
$145
10/4Fri
2 stops
13h 44mBOS-MDW
$155
6/16Sun
1 stopDelta
4h 28mBOS-MDW
$156
6/16Sun
1 stopDelta
4h 28mBOS-MDW
$158
9/20Fri
2 stops
12h 46mBOS-MDW
$168
6/30Sun
1 stopPorter Airlines
5h 42mBOS-MDW
$249
6/24Mon
2 stopsPorter Airlines
12h 52mBOS-MDW
$254

Search by stops

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Last minute flights from Boston to Midway

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 Boston to Chicago that are departing in the next 10 days.
6/12Wed
multi-stopFrontier
14h 40mBOS-MDW
6/18Tue
multi-stopFrontier
7h 42mMDW-BOS
$148
6/12Wed
multi-stopFrontier
14h 40mBOS-MDW
6/14Fri
multi-stopFrontier
13h 58mMDW-BOS
$195
6/11Tue
multi-stopFrontier
9h 44mBOS-MDW
6/14Fri
multi-stopFrontier
13h 58mMDW-BOS
$198
6/13Thu
multi-stopDelta
4h 28mBOS-MDW
6/17Mon
multi-stopDelta
5h 25mMDW-BOS
$336
6/12Wed
multi-stopDelta
4h 28mBOS-MDW
6/15Sat
multi-stopDelta
6h 42mMDW-BOS
$356
6/15Sat
multi-stop
19h 56mBOS-MDW
6/16Sun
multi-stop
16h 10mMDW-BOS
$971
6/12Wed
multi-stopPorter Airlines
19h 12mBOS-MDW
6/15Sat
multi-stopPorter Airlines
5h 22mMDW-BOS
$992
6/15Sat
multi-stop
22h 15mBOS-MDW
6/16Sun
multi-stop
16h 10mMDW-BOS
$1,135
6/12Wed
multi-stopPorter Airlines
5h 57mBOS-MDW
6/13Thu
multi-stopPorter Airlines
9h 05mMDW-BOS
$1,159
6/14Fri
multi-stopAir Transat
12h 52mBOS-MDW
6/16Sun
multi-stopAir Transat
16h 10mMDW-BOS
$1,167

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Boston - Chicago Midway Airport Flights

Departure:

Boston (BOS)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Boston

Cabin classes:

$377