Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

BOS - MDW

Find cheap flights from Boston to Chicago Midway Airport from $93

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 6/12. 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 5/28
Tue 6/4

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 43,219,010 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

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

Bundle and saveSave money when you bundle your flight + hotel.

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
8:21 am - 9:43 pmBOS-MDW
14h 22m1 stop
8:17 pm - 8:08 amMDW-BOS
10h 51m1 stop
$119Frontier
Find Deal
Wed, May 8 - Sat, May 11
12:46 pm - 11:30 pmBOS-MDW
11h 44m1 stop
9:08 pm - 9:43 amMDW-BOS
11h 35m1 stop
$120Frontier
Find Deal
Wed, May 8 - Sat, May 18
9:16 am - 9:33 amBOS-MDW
25h 17m1 stop
10:16 pm - 6:59 amMDW-BOS
7h 43m1 stop
$128Frontier
Find Deal
Wed, Jun 5 - Tue, Jun 11
6:30 am - 8:05 amBOS-MDW
2h 35mnonstop
7:20 pm - 10:35 pmMDW-BOS
2h 15mnonstop
$199Southwest
Find Deal
Sun, Jun 16 - Sat, Jun 22
6:30 am - 8:05 amBOS-MDW
2h 35mnonstop
4:10 pm - 11:40 pmMDW-BOS
6h 30m2 stops
$254Southwest
Find Deal
Sun, Jun 16 - Sat, Jun 22
6:30 am - 8:05 amBOS-MDW
2h 35mnonstop
8:35 am - 6:15 pmMDW-BOS
8h 40m1 stop
$259Southwest
Find Deal
Sun, Jun 16 - Sat, Jun 22
9:05 am - 5:06 pmBOS-MDW
9h 01m1 stop
5:00 pm - 11:49 pmMDW-BOS
5h 49m1 stop
$300Delta
Find Deal
Wed, May 22 - Sat, May 25
5:20 am - 8:48 amBOS-MDW
4h 28m1 stop
5:45 pm - 11:56 pmMDW-BOS
5h 11m1 stop
$314Delta
Find Deal
Tue, Jun 11 - Wed, Jun 12
9:15 am - 12:31 pmBOS-MDW
4h 16m1 stop
6:15 pm - 1:14 amMDW-BOS
5h 59m1 stop
$315Delta
Find Deal
Tue, Aug 6 - Sat, Aug 17
5:35 am - 9:06 amBOS-MDW
4h 31m1 stop
3:45 pm - 1:22 amMDW-BOS
8h 37m1 stop
$316Delta
Find Deal
Wed, Jun 5 - Sat, Jun 8

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, Monday 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 October, where tickets cost $294 on average. On the other hand, the most expensive months are May and June, where the average cost of tickets is $665 and $444 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure 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 average of all the values for each month.
To get a below average price on the flight from Boston to Chicago Midway Airport, you should book around 1 day before departure. For the absolute cheapest price, our data suggests you should book 57 days before departure.

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 $119 on Frontier, followed by Southwest ($199). One-way flight deals have also been found from as low as $93 on Frontier and from $157 on Delta.

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

Each day, there are between 3 and 4 nonstop flights that take off from Boston and land in Chicago Midway Airport, with an average flight time of 2h 35m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 25 flights. The most frequent day of departure is Monday, when 16% of all weekly flights depart. The fewest flights depart on a Tuesday.

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.

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

Direct flights take on average 2h 35m to travel the 857 miles between Boston and Chicago Midway Airport.

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

Early birds can take the earliest flight from Boston at 6:20 am and will be landing in Chicago Midway Airport at 7:55 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 9:55 pm and lands at 11:30 pm.

Good to know

Low season

January

High season

November

Cheapest flight

$93
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 10% increase in price.
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 $93 for a one-way ticket and $119 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?

    Delta, and JetBlue 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 $464 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 $147 and an overall rating of 6.3.

  • 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 10932 reviews
7.9comfort
8.2boarding
8.6crew
7.4food
8.0entertainment
Airline reviews

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

10.0 ExcellentRobert, Apr 2024BOS - RSW
Read more about Delta reviews

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

My only real complaint was how much turbulence there was-and that probably can't be avoided. I felt really sick getting off the plane. But boarding was super easy, the flight attendants were friendly, the bathroom was clean. Everything else about the flight was perfectly fine. Thanks!

Caroline (Supervisor) was great! Salute to the employees like her!

Boarding was good, staffs on the second flight to Korea was invisible all the time. Water was only offered 3 times during a 15 hours plus flight. It’s absolutely not enough for such a long flight!

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.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The flight and crew were fine. The entertainment- the sound was so bad through the headphones I could barely understand it and it was a show I had seen before. The food might have been fine but having to have an account with united in order to access the app in order to pay for the food was rage inducing. I had entered my credit card info at home and logged in as guest but that wouldn’t allow the “wallet” tab to open in the app. And then the wifi was so bad that it took about 45 minutes to fully log in and get all the info working at which time I missed the food. You shouldn’t have to give your address, email and phone number in order to get a hamburger.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

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.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

delayed delayed delayed. was supposed to have a 2 hour layover and very nearly missed my connection.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

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.
6/12Wed
1 stopFrontier
6h 38mBOS-MDW
$93
5/26Sun
1 stopFrontier
8h 13mBOS-MDW
$94
6/14Fri
1 stopFrontier
23h 42mBOS-MDW
$98
6/28Fri
1 stopFrontier
23h 42mBOS-MDW
$99
5/6Mon
3 stops
24h 08mBOS-MDW
$132
6/4Tue
1 stopDelta
6h 21mBOS-MDW
$157
7/3Wed
1 stopDelta
4h 29mBOS-MDW
$158
6/10Mon
2 stops
13h 45mBOS-MDW
$230
5/22Wed
1 stopPorter Airlines
9h 02mBOS-MDW
$280
5/31Fri
2 stopsPorter Airlines
12h 52mBOS-MDW
$284

Search by stops

Search by airline

Search by price

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.
5/1Wed
multi-stopFrontier
11h 44mBOS-MDW
5/4Sat
multi-stopFrontier
10h 51mMDW-BOS
$189
5/1Wed
multi-stopFrontier
11h 44mBOS-MDW
5/29Wed
multi-stopFrontier
23h 51mMDW-BOS
$199
5/3Fri
multi-stopFrontier
14h 17mBOS-MDW
5/4Sat
multi-stopFrontier
10h 51mMDW-BOS
$201
5/3Fri
multi-stopFrontier
14h 23mBOS-MDW
5/9Thu
multi-stopFrontier
13h 12mMDW-BOS
$212
4/30Tue
multi-stopDelta
6h 10mBOS-MDW
5/7Tue
multi-stopDelta
6h 46mMDW-BOS
$348
5/1Wed
nonstopSouthwest
2h 40mBOS-MDW
5/2Thu
nonstopSouthwest
2h 15mMDW-BOS
$381
5/1Wed
multi-stopSouthwest
4h 25mBOS-MDW
5/2Thu
nonstopSouthwest
2h 15mMDW-BOS
$390
5/3Fri
multi-stopDelta
4h 14mBOS-MDW
5/6Mon
multi-stopDelta
4h 39mMDW-BOS
$443
5/2Thu
multi-stopPorter Airlines
6h 12mBOS-MDW
5/6Mon
multi-stopPorter Airlines
9h 05mMDW-BOS
$999
5/1Wed
multi-stopPorter Airlines
19h 12mBOS-MDW
5/5Sun
multi-stopPorter Airlines
14h 42mMDW-BOS
$1,089

Search by stops

Search by airline

Search by price

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