MDW - BOS

$68 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 4/12. 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.
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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
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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.

Recent round-trip flight deals from Midway to Boston

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Boston.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:05 pm - 10:15 pmMDW-BOS
2h 10mnonstop
5:45 am - 7:35 amBOS-MDW
2h 50mnonstop
$147Southwest
Find Deal
Tue, Mar 18 - Wed, Mar 26
4:40 pm - 12:47 amMDW-BOS
7h 07m1 stop
6:00 am - 9:24 amBOS-MDW
28h 24m1 stop
$150Frontier
Find Deal
Tue, Apr 1 - Wed, Apr 2
4:40 pm - 12:47 amMDW-BOS
7h 07m1 stop
6:00 am - 4:08 pmBOS-MDW
11h 08m1 stop
$151Frontier
Find Deal
Tue, Apr 8 - Tue, Apr 15
4:40 pm - 12:47 amMDW-BOS
7h 07m1 stop
6:00 am - 4:08 pmBOS-MDW
11h 08m1 stop
$152Frontier
Find Deal
Tue, Apr 8 - Tue, Apr 15
4:40 pm - 12:47 amMDW-BOS
7h 07m1 stop
6:00 am - 11:24 pmBOS-MDW
18h 24m1 stop
$154Frontier
Find Deal
Tue, Apr 1 - Tue, Apr 8
8:35 pm - 11:50 pmMDW-BOS
2h 15mnonstop
5:45 am - 7:35 amBOS-MDW
2h 50mnonstop
$167Southwest
Find Deal
Mon, Mar 17 - Wed, Mar 19
6:30 pm - 9:45 pmMDW-BOS
2h 15mnonstop
7:15 pm - 11:55 pmBOS-MDW
5h 40m1 stop
$177Southwest
Find Deal
Sat, Apr 12 - Sun, Apr 13
2:55 pm - 11:47 pmMDW-BOS
7h 52m1 stop
5:30 am - 12:36 pmBOS-MDW
8h 06m1 stop
$233Delta
Find Deal
Tue, Mar 25 - Thu, Mar 27
5:55 pm - 10:56 pmMDW-BOS
4h 01m1 stop
5:20 am - 12:28 pmBOS-MDW
8h 08m1 stop
$275Delta
Find Deal
Sat, May 24 - Tue, May 27
5:55 pm - 10:56 pmMDW-BOS
4h 01m1 stop
5:20 am - 8:40 amBOS-MDW
4h 20m1 stop
$317Delta
Find Deal
Sat, May 24 - Tue, May 27

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 round-trip 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 Saturday, 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 Thursday and avoiding Sundays 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 round-trip 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 $185 (return) on average. On the other hand, the most expensive months are July and February, where the average cost of round-trip tickets is $344 and $323 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.
To get a below average price on the flight from Chicago Midway Airport to Boston, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low season

July

High season

December

Cheapest flight

$68
Best time to beat the crowds but there is an average 21% increase in price.
Most popular time to fly with an average 5% 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 $147 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, Delta, and JetBlue 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 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.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Boston are Southwest and Delta. With an average price for the route of $287 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $366 and an overall rating of 8.0.

  • 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

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Boston

  • Looking for a cheap flight? 25% of our users found flights on this route for $108 or less one-way and $197 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Boston?

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

Direct 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

Direct 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
SouthwestOverall score based on 4315 reviews
8.7Crew
8.2Boarding
7.1Food
7.6Entertainment
8.1Comfort
Airline reviews

WiFi on the flight was not working. Thus, entertainment options were limited.

8.0 ExcellentJames, Feb 2025SRQ - DEN
Read more Southwest reviews

WiFi on the flight was not working. Thus, entertainment options were limited.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

The crew was wonderful and attentive. The seats near exit row were restrictive. Offer healthy snacks please

Delta is a premier airline so my expectations are most always met.

Seats are much much more comfortable than United, which is what I usually fly

Zero updates from the pilots for 30 minutes in the tarmac

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

They changed the timing , first delayed by 4 hours then went back to 40 mins late, we had to run back to airport to not miss our flight. This is ridiculous

Seats were extremely uncomfortable and it was very hot on the plane.

Would be great if Frontier can Assign Seats together under one PNR

Early arrival. Great landing. Pilot updates. Too cold in plane.

Better to put road truck seat in plain it so uncomfortable can not adjustable and fill metal don’t have cushions at all it’s very hard to travel for five hours

Since they are a budget airline, I wasn’t expecting too much but they did some things well. They were on time, the plane was clean, boarding was fairly straightforward and the staff was cheerful and friendly. The only downside was comfort. The seats were fairly hard and after a 2 hour flight your rear end is not feeling so great. Maybe a little more cushion in the seats, Frontier!

They cancelled the flight and did nothing. I should be compensated for my uber rides to and from airport. Not a good service by frontier or kayak.

No frills for sure. No gate announcements about flight delay, not even water to drink on the flight.

food not having to pay for it, reclining seat would be nice, more leg room, HEAT!!!!!!!

An absolutely fraudulent experience. Extremely unprofessional. Terrible in all ways possible. Rude staff, flight attendants, and deceptive "policies."

Everything you need to know for your flight from Midway to Boston

Information on your arrival and departure airports

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