MDW - BOS

$60 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 1/21. 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
$122
Overall average: $317
Southwest
Fri 10/31Sat 11/1
MDW - BOS • Non-stop
Cheapest non-stop
$124
Typical prices: $187-$358
Southwest
Tue 2/24Sat 2/28
MDW - BOS • Non-stop
Our travelers' advice
AI-generated summary based on content written by travel experts
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 $122 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 25% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 40% price drop
December
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

Fri, Oct 31 - Sat, Nov 1
Southwest Logo
4:55 pm - 8:10 pmMDW-BOS
2h 15mnonstop
Southwest Logo
1:10 pm - 8:20 pmBOS-MDW
8h 10m1 stop
$122Southwest
Find Deal
Thu, Nov 13 - Thu, Nov 20
Southwest Logo
7:15 pm - 10:30 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:30 am - 7:15 amBOS-MDW
2h 45mnonstop
$127Southwest
Find Deal
Thu, Nov 6 - Thu, Nov 13
Southwest Logo
9:10 am - 6:10 pmMDW-BOS
8h 00m1 stop
Southwest Logo
5:15 am - 7:00 amBOS-MDW
2h 45mnonstop
$128Southwest
Find Deal
Tue, Jan 6 - Tue, Jan 13
Southwest Logo
5:35 pm - 8:50 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:30 am - 7:20 amBOS-MDW
2h 50mnonstop
$129Southwest
Find Deal
Sun, Jan 18 - Fri, Jan 23
Frontier Logo
2:12 pm - 12:58 amMDW-BOS
9h 46m1 stop
Frontier Logo
6:00 am - 11:25 pmBOS-MDW
18h 25m1 stop
$133Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Delta Logo
10:36 am - 5:15 pmMDW-BOS
5h 39m1 stop
Delta Logo
9:00 am - 12:34 pmBOS-MDW
4h 34m1 stop
$137Delta
Find Deal
Thu, Dec 4 - Sun, Dec 7
Delta Logo
10:36 am - 6:14 pmMDW-BOS
6h 38m1 stop
Delta Logo
5:29 am - 8:54 amBOS-MDW
4h 25m1 stop
$141Delta
Find Deal
Wed, Dec 24 - Wed, Dec 31
Frontier Logo
8:15 am - 1:14 amMDW-BOS
15h 59m1 stop
Frontier Logo
11:09 am - 10:12 pmBOS-MDW
12h 03m1 stop
$169Frontier
Find Deal
Thu, Nov 20 - Wed, Dec 3
Multiple Airlines Logo
6:05 am - 12:44 amMDW-BOS
17h 39m1 stop
Multiple Airlines Logo
9:54 pm - 6:04 pmBOS-MDW
21h 10m1 stop
$179Multiple Airlines
Find Deal
Tue, Dec 2 - Thu, Dec 4
Multiple Airlines Logo
7:44 am - 10:57 pmMDW-BOS
14h 13m2 stops
Multiple Airlines Logo
11:28 am - 6:08 pmBOS-MDW
7h 40m1 stop
$180Multiple Airlines
Find Deal
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 Wednesday, 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 January, where tickets cost $173 (return) on average. On the other hand, the most expensive months are September and February, where the average cost of round-trip tickets is $330 and $323 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 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Expert advice

Expert advice for your flight from Midway to Boston

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
MDW

Midway offers a compact and easy-to-navigate terminal with a variety of dining and shopping options, perfect for a quick pre-flight visit.

Read more about MDWby Stefanie Waldek
BOS

The Silver Line bus from BOS to downtown Boston is free and takes about 20-30 minutes, offering a convenient and budget-friendly option.

Read more about BOSby Blane Bachelor
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

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

Blane Bachelor

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$60
Best time to beat the crowds with an average 40% drop 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 $60 for a one-way ticket and $122 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, JetBlue, and Delta 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.

  • 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 $68 or less one-way and $177 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

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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 4236 reviews
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
Airline reviews

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

10.0 ExcellentStacy, Oct 2025SMF - DEN
Read more Southwest reviews

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

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

Information on your arrival and departure airports

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