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Find cheap flights from Chicago Midway Airport to Boston from $68

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 5/15. 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
Thu 4/18
Thu 4/25

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 47,600,107 times on KAYAK, and here is why:

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Cheap flight deals from Midway to Boston

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.
5:56 pm - 8:08 amMDW-BOS
13h 12m1 stop
12:41 pm - 10:41 pmBOS-MDW
11h 00m1 stop
$96Frontier
Find Deal
Thu, May 2 - Sat, May 11
8:17 pm - 8:08 amMDW-BOS
10h 51m1 stop
12:41 pm - 10:41 pmBOS-MDW
11h 00m1 stop
$98Frontier
Find Deal
Sat, Apr 13 - Sat, Apr 20
5:56 pm - 8:08 amMDW-BOS
13h 12m1 stop
12:41 pm - 11:30 pmBOS-MDW
11h 49m1 stop
$99Frontier
Find Deal
Thu, May 9 - Mon, May 13
8:05 am - 8:45 amMDW-BOS
23h 40m1 stop
11:53 am - 5:01 pmBOS-MDW
6h 08m1 stop
$105Frontier
Find Deal
Wed, Apr 3 - Tue, Apr 9
6:08 pm - 7:21 amMDW-BOS
12h 13m1 stop
10:01 am - 6:27 pmBOS-MDW
9h 26m1 stop
Wed, Apr 17 - Wed, Apr 24
7:00 am - 2:49 pmMDW-BOS
6h 49m1 stop
10:01 am - 6:23 pmBOS-MDW
9h 22m1 stop
Tue, Apr 16 - Tue, Apr 23
1:25 pm - 11:30 pmMDW-BOS
9h 05m1 stop
6:55 am - 8:35 amBOS-MDW
2h 40mnonstop
$246Southwest
Find Deal
Tue, Mar 26 - Wed, Mar 27
2:50 pm - 11:30 pmMDW-BOS
7h 40m2 stops
6:55 am - 8:35 amBOS-MDW
2h 40mnonstop
$251Southwest
Find Deal
Tue, Mar 26 - Wed, Mar 27
1:21 pm - 11:28 pmMDW-BOS
9h 07m1 stop
9:05 am - 4:35 pmBOS-MDW
8h 30m1 stop
$282Delta
Find Deal
Tue, May 14 - Wed, May 15
6:00 pm - 11:24 pmMDW-BOS
4h 24m1 stop
5:35 am - 8:50 amBOS-MDW
4h 15m1 stop
$315Delta
Find Deal
Wed, May 1 - Sun, May 5

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 Monday, 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 Mondays 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 February, where tickets cost $158 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $336 and $324 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 $96 on Frontier, followed by Southwest ($246). One-way flight deals have also been found from as low as $68 on Frontier and from $113 on Allegiant Air.

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

Each day, there are between 5 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 6:00 am and most flights take off in the morning. Each week, there are 47 flights. The most frequent day of departure is Thursday, when 17% 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 10m 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 6:15 am and will be landing in Boston at 9:30 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 8:30 pm and lands at 11:45 pm.

Good to know

Low season

April

High season

October

Cheapest flight

$68
Best time to beat the crowds with an average 52% drop in price.
Most popular time to fly with an average 37% increase in price.
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 $68 for a one-way ticket and $96 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?

    Only American Airlines offers 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 Boeing 737-800 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.

  • 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 airlines flying from Midway to Boston

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 KAYAK reviews.
8.0
DeltaOverall score based on 11551 reviews
81entertainment
82boarding
79comfort
86crew
81overall
75food
Airline reviews

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

Read more about Delta

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

I was traveling with my 85 years old grandma and 60 years old mother. Which I requested to get a wheelchair. I went to the Delta Kiosk and asked for a wheelchair.  They brought a wheelchair and 2 minutes (without exaggerating, time is important for me as I am well disciplined with a military background) later they said that the wheelchair belongs to American Airlines, so we need to switch it.  We were like where is the other one so my grandma can use it? They are like, "it's on its way, she has to wait for the other one" I asked them why does she have to wait? Is it ok for her to sit on this one when the other one arrives. Answer was "NO". I guess lack of common sense was the issue. I started to explain to the agent that she can not stand still or wait. Finally, someone said that in spanish "she can not stand, let's wait for the other one" . Delta's wheelchair came, without an attendant or helper. They brought that wheelchair and left it in the middle of the airport. Nobody seemed to care. I had to push her to the gate. Then they finally realized that "wait a minute, there is something wrong with that". So they send someone, who later started harassing us, to tell us how he works for cash tips. Then a "Private Security Interviewer" approached us. I think his name was Carlos (His descriptions - tall for an average worker, ginger curly hair, wears glasses, overweight). He did not represent himself. All he did was show his badge for two seconds and when (later on) I asked him what his name was, he said "I already told you at the beginning". At that point we were waiting to be called at the Delta Kiosk (this is prior to the Customs first check in point). So, Delta Airlines hired "Private security interviewers" to make sure that nobody brings anything illegally to the US. Which is great, makes me feel safe and secure. But, it does not serve the purpose. Let me explain to you why. These interviewers do not know what they are doing or saying and you can clearly see that. They think that they are CBP or Immigration officers. They will get angry If you ask them any questions. Then they will put all these stickers on the back of your passport like they caught "Pablo Escobar". At one point I was sarcastic and told the interviewer that "I like those stickers, It's my hobby and I am collecting them. Can I have more of those?"  and interviewers eyes and brain goes like "error 404". He did not know how to react or respond to that. Then he flags my itinerary on his iPad. Trying to give me a hard time since I asked him about his name, so I can call him by his name. But of course that did not change the fact that his lack of english made everything even harder. After 45 mins of wait and clearing the "Private Security Interviewer" you would think that we are going to be all set to depart. I was wrong. We waited in line to go through the security line, just like other citizens. No wheelchair, disability, seniority etc were important for her. They treat us like she is in her twenties.  On several occasions they forced her to stand up. She was like "I swear to God that I can not walk, my son I wish I could walk, but I can not". They did not seem like they cared. Then finally they realized that she is legit disabled. They let her pass on a wheelchair. At the gate, Carlos showed up to make sure that I am going through the secondary check. They pulled me to the secondary check. And started asking me about my luggage. My response was "I only have one carry-on bag, to make everyone's (including my life) life easier". They asked the same question over again "Sir, do you just have only one bag?" I replied saying "Yes". She did not believe me and said "Just only one". So, I thought she did not believe me and I said "Yes, Si, Si, solo uno". She looked at me and then turned to the agent (Carlos) and stared at him like "did you not ask him about his bags, did you not know that he only had one carry on?". I am sorry to say that but they just looked like a bunch of idiots who do not know what they are doing. Finally they released me after a minute of secondary check. Meanwhile everyone is boarding and my grandma is waiting on her wheelchair. Then we approached the gate agent and I asked her if I could sit next to my family, if they had any seats available. She replied that "I can not change any seat at the gate, I do not have any authority". I replied "I understood". We got on the plane last and I asked our flight attendant if I could change my seat to be next to my family. FYI, their seats were 10 B and C, mine was the 35 D. Meanwhile there were empty seats on 10 D and F. Even flight attendants surprisingly said that "why did she put you all the way back, while we had 1/2 full flight. I will go and ask her". Our flight attendant was great and he made sure that I am next to my family. He went above and beyond and he gave the closest seat to the. Flight was good. Delta Airlines failed to bring the wheelchair when we arrived. Excuse was "Gate changed, that is why". I walked outside and grabbed an empty wheelchair. I put my grandma and brought her to the Customs. Then a Delta Airline worker approaches me and says that you can not move this wheelchair, it belongs to the gate. We will bring you a new one. A CBP officer heard our conversation and jumped in and said, "wait a minute you want her (pointed my grandma) to wait here while you bring her wheelchair?". He (delta worker) responded "yes sir". But when he talks to me, no sir, nothing. The CBP officer goes "Nope, she is not waiting here and I will make sure to pull her wheelchair". If that officer was not there we probably would have had to wait and be forced to change the wheelchair. The CBP officer, again the CBP officer, not the Delta employee, pushed our wheelchairs to the gate. Sincerely,

The boarding agents appeared to do the minimum customer service. They did not appear to try to find solutions to problems.

The only real hiccups in the flight were things beyond Delta’s control - turbulence which delayed food service and a departure delay caused by some VIP plane which stopped all departures and landings for 30 minutes - and was never explained to us by the crew. Otherwise good flight. I would fly Delta again.

Checkin was easy, boarding was organized, employees friendly and nice. Was a lovely flight.

I understand why there was a 40 minute delay, but we should have been offered snacks during that time. We weren’t offered it until later.

Delta airlines charge $ 30,oo US DOLLARS for the check in for a suitcase in the baggage hold

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.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Unfortunately our flight was delayed by 45 minutes due to Kate arriving aircraft. Once we stated everything was great.

Flight canceled due to weather. Rescheduled flight canceled due to maintenance. I’m stuck!

You could have been ON TIME! And I was miffed because I spent an extra $82 to get my seat and the steward put a woman from the back in my aisle for nothing because her movies wouldn’t work. I’ll try that next time and save $82!

For some strange reason I was put in zone 5 for boarding even though I had paid premium price for a premium seat right behind business class. This must have been a flaw because everyone else around me in the same zone (row) had been placed in zone 3.

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.
5/15Wed
1 stopFrontier
12h 17mMDW-BOS
$68
3/26Tue
1 stopFrontier
15h 09mMDW-BOS
$69
4/7Sun
1 stopFrontier
13h 19mMDW-BOS
$70
3/27Wed
2 stops
19h 45mMDW-BOS
$101
4/29Mon
2 stops
18h 32mMDW-BOS
$103
4/7Sun
1 stopAllegiant Air
13h 22mMDW-BOS
$113
4/30Tue
1 stopDelta
7h 09mMDW-BOS
$158
4/16Tue
1 stopDelta
7h 09mMDW-BOS
$159
3/25Mon
1 stopSouthwest
5h 25mMDW-BOS
$174
3/25Mon
2 stopsSouthwest
7h 10mMDW-BOS
$218

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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.
3/20Wed
multi-stopFrontier
16h 29mMDW-BOS
4/2Tue
multi-stopFrontier
9h 40mBOS-MDW
$339
3/20Wed
multi-stop
24h 51mMDW-BOS
3/26Tue
multi-stop
6h 08mBOS-MDW
$345
3/20Wed
multi-stop
24h 51mMDW-BOS
4/2Tue
multi-stop
6h 08mBOS-MDW
$346
3/20Wed
multi-stopDelta
5h 50mMDW-BOS
3/27Wed
multi-stopDelta
7h 00mBOS-MDW
$347
3/20Wed
multi-stopFrontier
18h 17mMDW-BOS
3/26Tue
multi-stopFrontier
6h 08mBOS-MDW
$348
3/20Wed
multi-stopDelta
5h 50mMDW-BOS
3/28Thu
multi-stopDelta
6h 02mBOS-MDW
$351
3/24Sun
nonstopSouthwest
2h 10mMDW-BOS
3/25Mon
multi-stopSouthwest
7h 40mBOS-MDW
$353
3/20Wed
multi-stopFrontier
15h 15mMDW-BOS
4/2Tue
multi-stopFrontier
6h 08mBOS-MDW
$373
3/20Wed
multi-stopDelta
5h 50mMDW-BOS
3/23Sat
multi-stopDelta
4h 22mBOS-MDW
$382
3/24Sun
multi-stopSouthwest
6h 00mMDW-BOS
3/27Wed
nonstopSouthwest
2h 45mBOS-MDW
$434

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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:

$542