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BOS - MDW

Find cheap flights from Boston to Chicago Midway Airport from $54

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 5/9. 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
Sun 4/28
Sun 5/5

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 46,342,885 times on KAYAK, and here is why:

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Cheap flight deals from Boston to Midway

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
12:41 pm - 10:41 pmBOS-MDW
11h 00m1 stop
8:17 pm - 8:08 amMDW-BOS
10h 51m1 stop
$96Frontier
Find Deal
Sat, Apr 27 - Sat, May 4
9:08 am - 5:05 pmBOS-MDW
8h 57m1 stop
8:17 pm - 8:08 amMDW-BOS
10h 51m1 stop
$98Frontier
Find Deal
Thu, May 9 - Sat, May 11
8:21 am - 9:43 pmBOS-MDW
14h 22m1 stop
8:17 pm - 8:08 amMDW-BOS
10h 51m1 stop
$101Frontier
Find Deal
Wed, May 8 - Sat, May 11
12:41 pm - 10:41 pmBOS-MDW
11h 00m1 stop
6:27 pm - 8:08 amMDW-BOS
12h 41m1 stop
$104Frontier
Find Deal
Sat, Apr 27 - Sun, Apr 28
8:21 am - 5:01 pmBOS-MDW
9h 40m1 stop
8:17 pm - 8:08 amMDW-BOS
10h 51m1 stop
$106Frontier
Find Deal
Tue, Apr 9 - Sat, Apr 13
9:08 am - 11:52 amBOS-MDW
27h 44m1 stop
7:17 pm - 2:49 pmMDW-BOS
18h 32m2 stops
Sat, May 4 - Mon, May 6
6:00 am - 5:13 pmBOS-MDW
12h 13m1 stop
5:45 am - 3:13 pmMDW-BOS
8h 28m1 stop
Mon, May 13 - Wed, May 15
9:30 am - 8:17 pmBOS-MDW
11h 47m1 stop
9:23 pm - 11:45 amMDW-BOS
13h 22m1 stop
$307Allegiant Air
Find Deal
Fri, Apr 5 - Sun, Apr 7
6:05 am - 11:02 amBOS-MDW
5h 57m1 stop
6:00 am - 12:15 pmMDW-BOS
5h 15m1 stop
$316Delta
Find Deal
Sat, May 11 - Tue, May 14
6:05 am - 5:06 pmBOS-MDW
12h 01m2 stops
9:32 am - 5:45 pmMDW-BOS
7h 13m1 stop
$317Delta
Find Deal
Tue, May 7 - Wed, May 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 Monday, 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 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 $96 on Frontier, followed by Allegiant Air ($307). One-way flight deals have also been found from as low as $54 on Frontier and from $159 on Delta.

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

Each day, there are between 3 and 8 nonstop flights that take off from Boston and land in Chicago Midway Airport, with an average flight time of 2h 38m. The most common departure time is 10:00 am and most flights take off in the morning. Each week, there are 42 flights. The most frequent day of departure is Thursday, when 19% of all weekly flights depart. The fewest flights depart on a Wednesday.

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 5h 32m 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 5:55 am and will be landing in Chicago Midway Airport at 7:40 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

$54
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 $54 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 Embraer 190 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 $454 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

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 KAYAK reviews.
8.0
DeltaOverall score based on 11402 reviews
80entertainment
75food
82boarding
86crew
81overall
79comfort
Airline reviews

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

Read more about Delta

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!

Traveling with delta is always a pleasure from the take off to the landing 🛬 🥰

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

Very crowded flight… a little disorganized.. why don’t they boatd the back of the plane first??

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.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The flights from Ottawa to Albuquerque went smoothly enough though on on flight they didn't have how water for coffee or tea and on another there there was no ice. The return flights from Albuquerque were delayed by mechanical problems on both flights. Ottawa was a ground crew maintenance issue.

The male air hostess was rude and didn’t provide good customer service. Didn’t even offer me a drink

There was no in seat entertainment, you had to spend $10 on their wifi which worked poorly at best. You were allowed ONE one oz snack for a 3.5 hour flight. Seats were made for midgets. I am a regular size adult male and I had to wedge myself in. Not a fan.

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.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Perfect flight. On time departure and early arrival. Smooth flight.

Overall pleasant was delayed and caused transportation issue when landing

The arriving flight was a few minutes late, but the gate crew helped to deplane and board our outgoing flight quickly and efficiently. We were able to depart quickly and arrive at ORD almost at the posted time. Great job.

Nothing, flight was supposed to leave at 758 am. My flight didn’t leave until 430 pm. Spent the whole day at the airport.

Despite a bumpy flight the pilot was great. The rest of the crew on the other hand couldn’t care less if a passenger would colapse and die. Horrible service, robot like, lifeless…

The boarding time. I was in Section 1 the lady in charge just let people in section 3 without see us. Make a line , I have to step out and ask her. We were in the line and she just take my ticket and that’s it, so if I don’t ask her she could leave us at the end! We paid more for that privilege and. She doesn’t care….

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

I hope to avoid flying with them in the future. First flight got cancelled then got stuck with a 13 hour layover in Denver. The process was long and frustrating to many people.

First time flying Frontier, I am not sure the Ala Carte menu of options is for me.

Flight was delayed on the runway for 40 minutes the crew did not even offer even water to passengers to compensate for the flight delayed. The flight was delayed due to aircraft mechanical issues. Worst customer service ever

See my previous comment which is mostly about our flight from Phoenix to SFO

Terrible. Initially we were shocked by the outrageous baggage fees we needed to pay at check in for our so-called "discounted, economy flight" - we paid over $200 (!!) for one check-in and 2 carry-on bags - this felt like a real bait-and-switch" scam. Our flight from Phoenix to SFO was delayed by 4 hours. Multiple apparent causes (from needing to make space for other planes that were landing late to problem with cabins pressure system, and whatever...). After de-boarding and re-boarding we still waited at least an hour on a cramped, poorly ventilated plane before take-off. Seats were cramped, uncomfortable - did not recline at all. No water until we were flying for a while. No complimentary snacks. Upon arrival at SFO my luggage was sent upstairs to the check-in counter. The customer service person there refused to let me examine a bunch of bags that were sitting on a nearby cart because it was "behind the counter", rather made me wait until another attendant did an exhaustive and failed (?computer) search, came back and told me they were unable to locate my bag. I asked her to look on the cart, lo and behold, there was my bag just a few feet away! Missed my choir rehearsal that evening due to all of the delays. One more thing, a few days later my husband and I tested positive for Covid. Since we both are fully vaccinated, careful about masking and have never had Covid previously, we will never know, but suspect we may have acquired the infection during the prolonged wait on your poorly ventilated plane (person in the row in front of us was coughing). After registering a complaint, we received a measly $50 voucher for future flights. Needless to say we have no intention of flying with Frontier Airlines ever again.

I liked getting off the plane. Everything else was well below standards. Not even offering a bag of peanuts for free for a 4 hours flight is ridiculous.

The whole experience was bad. Didn't know no complimentary drinks or snacks. $4.39 for a soda is ridiculous even a bottle water. A carry on was $74 just crazy. I don't think I will take this airline ever again. Very bad

Delayed...attendants checked every single bag and item for sizes before boarding.

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.
5/9Thu
1 stopFrontier
8h 57mBOS-MDW
$54
4/17Wed
1 stopFrontier
11h 37mBOS-MDW
$55
4/23Tue
2 stops
15h 44mBOS-MDW
$88
5/20Mon
1 stop
15h 15mBOS-MDW
$89
6/16Sun
1 stopDelta
4h 20mBOS-MDW
$159
4/4Thu
2 stopsAllegiant Air
32h 35mBOS-MDW
$181
7/21Sun
1 stopDelta
4h 39mBOS-MDW
$204
5/31Fri
3 stopsPorter Airlines
20h 37mBOS-MDW
$287
7/14Sun
2 stopsAllegiant Air
25h 11mBOS-MDW
$306
4/27Sat
2 stopsPorter Airlines
6h 42mBOS-MDW
$459

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.
4/2Tue
multi-stopFrontier
6h 08mBOS-MDW
4/6Sat
multi-stopFrontier
10h 56mMDW-BOS
$227
4/2Tue
multi-stopFrontier
6h 08mBOS-MDW
4/5Fri
multi-stopFrontier
10h 41mMDW-BOS
$231
4/2Tue
multi-stopFrontier
6h 08mBOS-MDW
4/3Wed
multi-stopFrontier
11h 02mMDW-BOS
$278
3/30Sat
multi-stopFrontier
6h 08mBOS-MDW
4/6Sat
multi-stopFrontier
10h 56mMDW-BOS
$291
4/1Mon
multi-stopDelta
6h 02mBOS-MDW
4/8Mon
multi-stopDelta
5h 29mMDW-BOS
$348
3/30Sat
multi-stopDelta
7h 49mBOS-MDW
4/6Sat
multi-stopDelta
5h 31mMDW-BOS
$352
4/1Mon
multi-stopAllegiant Air
10h 49mBOS-MDW
4/4Thu
multi-stopAllegiant Air
13h 22mMDW-BOS
$354
3/31Sun
multi-stopFrontier
30h 20mBOS-MDW
4/2Tue
multi-stopFrontier
12h 11mMDW-BOS
$357
4/2Tue
multi-stop
17h 11mBOS-MDW
4/6Sat
multi-stop
7h 26mMDW-BOS
$377
4/1Mon
multi-stop
10h 49mBOS-MDW
4/2Tue
multi-stop
16h 34mMDW-BOS
$408

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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:

$562