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 5/30. 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
1 adult, Economy, 0 bags

KAYAK searches 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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$125
Overall average: $332
Southwest
Sat 4/4Sat 4/11
MDW - BOS • 1 stop
Cheapest non-stop
$126
Typical prices: $287-$363
Southwest
Sat 4/11Mon 4/13
MDW - BOS • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Midway's compact terminal eases pre-flight navigation.
The Silver Line bus from BOS to downtown is free.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Southwest
Cheapest • from $125 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 14m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Southwest
Most punctual • 76% on-time
Night flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 41% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
July
Cheapest • 14% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Boston!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Boston

Sat, Apr 4 - Sat, Apr 11
Southwest Logo
6:25 am - 1:45 pm
MDW
-
BOS
6h 20m
1 stop
Southwest Logo
1:50 pm - 3:30 pm
BOS
-
MDW
2h 40mnonstop
$125Southwest
Sat, Apr 11 - Mon, Apr 13
Southwest Logo
11:25 am - 2:45 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
3:45 pm - 5:30 pm
BOS
-
MDW
2h 45mnonstop
$126Southwest
Sat, Apr 4 - Sat, Apr 11
Southwest Logo
6:45 pm - 10:00 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
1:50 pm - 3:30 pm
BOS
-
MDW
2h 40mnonstop
$136Southwest
Thu, May 7 - Mon, May 11
Southwest Logo
9:25 am - 12:40 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
10:40 am - 12:20 pm
BOS
-
MDW
2h 40mnonstop
$137Southwest
Wed, Mar 25 - Sat, Mar 28
Southwest Logo
12:10 pm - 3:20 pm
MDW
-
BOS
2h 10mnonstop
Southwest Logo
6:30 am - 8:20 am
BOS
-
MDW
2h 50mnonstop
$140Southwest
Sat, May 9 - Wed, May 13
Southwest Logo
4:20 pm - 11:40 pm
MDW
-
BOS
6h 20m
2 stops
Southwest Logo
7:20 am - 9:05 am
BOS
-
MDW
2h 45mnonstop
$141Southwest
Sun, Apr 19 - Sat, Apr 25
Southwest Logo
8:15 am - 6:25 pm
MDW
-
BOS
9h 10m
1 stop
Southwest Logo
9:25 am - 11:05 am
BOS
-
MDW
2h 40mnonstop
$142Southwest
Sat, Apr 4 - Sat, Apr 11
Southwest Logo
5:40 pm - 11:05 pm
MDW
-
BOS
4h 25m
1 stop
Southwest Logo
1:50 pm - 3:30 pm
BOS
-
MDW
2h 40mnonstop
$146Southwest
Sat, Apr 11 - Tue, Apr 14
Southwest Logo
9:15 am - 5:20 pm
MDW
-
BOS
7h 05m
1 stop
Southwest Logo
2:25 pm - 4:05 pm
BOS
-
MDW
2h 40mnonstop
$147Southwest
Wed, Mar 25 - Sat, Mar 28
Southwest Logo
3:35 pm - 11:25 pm
MDW
-
BOS
6h 50m
1 stop
Southwest Logo
6:30 am - 8:20 am
BOS
-
MDW
2h 50mnonstop
$150Southwest
Booking Insights

KAYAK's insights & trends for Midway to Boston flights

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 Wednesday 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 July, where tickets cost $247 (return) on average. On the other hand, the most expensive months are January and April, where the average cost of round-trip tickets is $414 and $332 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to Boston?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $214 on average.

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, which saves you about 41% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Find deals
Expert advice

Expert advice for your flight from Midway to Boston

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Blane Bachelor

Blane Bachelor

Expert on BOS

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more

Good to know

Low seasonJanuary
Cheapest flight$68
Best time to beat the crowds but there is an average 43% increase in price.
Most popular time to fly with an average 4% 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 $125 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 Embraer 175 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.

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 $78 or less one-way and $146 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Boston?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Boston Logan Intl.
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

Reviews of the top airline flying 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 4317 reviews
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Boston (BOS)