BOS - MDW

$68 Find Cheap Flights from Boston to Chicago Midway Airport

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 2/11. 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 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
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
$135
Overall average: $219
Southwest
Wed 2/25Wed 3/4
BOS - MDW • Non-stop
Cheapest one-way
$68
Typical prices: $108-$166
Southwest
Wed 2/11
BOS - MDW • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
Use the FlyLogan app for gate info and dining orders.
Take the CTA Orange Line from MDW to downtown Chicago.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Southwest
Cheapest • from $135 (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 38% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
December
Cheapest • 46% price drop
July
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 Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Boston to Midway (BOS-MDW)

 
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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Boston to Midway

Wed, Feb 25 - Wed, Mar 4
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
5:35 pm - 8:50 pm
MDW
-
BOS
2h 15mnonstop
$135Southwest
Thu, Feb 5 - Tue, Mar 3
Southwest Logo
5:20 am - 7:10 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
2:00 pm - 5:10 pm
MDW
-
BOS
2h 10mnonstop
$146Southwest
Thu, Feb 26 - Mon, Mar 2
Frontier Logo
6:00 am - 4:16 pm
BOS
-
MDW
11h 16m
1 stop
Frontier Logo
2:19 pm - 1:13 am
MDW
-
BOS
9h 54m
1 stop
$148Frontier
Wed, Feb 25 - Sun, Mar 1
Multiple Airlines Logo
5:50 pm - 1:56 pm
BOS
-
MDW
21h 06m
1 stop
Multiple Airlines Logo
9:04 pm - 1:13 am
MDW
-
BOS
27h 09m
1 stop
$149Multiple Airlines
Thu, Feb 26 - Mon, Mar 2
Frontier Logo
6:00 am - 4:16 pm
BOS
-
MDW
11h 16m
1 stop
Frontier Logo
2:19 pm - 1:13 am
MDW
-
BOS
9h 54m
1 stop
$150Frontier
Fri, Feb 27 - Mon, Mar 2
Frontier Logo
6:00 am - 10:37 pm
BOS
-
MDW
17h 37m
1 stop
Frontier Logo
2:19 pm - 1:13 am
MDW
-
BOS
9h 54m
1 stop
$151Frontier
Wed, Feb 25 - Mon, Mar 2
Delta Logo
11:15 am - 5:45 pm
BOS
-
MDW
7h 30m
1 stop
Delta Logo
6:20 pm - 11:26 pm
MDW
-
BOS
4h 06m
1 stop
$152Delta
Mon, Feb 9 - Wed, Feb 11
Frontier Logo
6:00 am - 11:45 am
BOS
-
MDW
6h 45m
1 stop
Frontier Logo
6:15 am - 1:13 am
MDW
-
BOS
17h 58m
1 stop
$154Frontier
Wed, Feb 25 - Sun, Mar 1
Southwest Logo
2:40 pm - 4:30 pm
BOS
-
MDW
2h 50mnonstop
Southwest Logo
6:05 am - 9:25 am
MDW
-
BOS
2h 20mnonstop
$155Southwest
Sat, Feb 7 - Sun, Feb 8
Southwest Logo
4:55 pm - 6:45 pm
BOS
-
MDW
2h 50mnonstop
Southwest Logo
5:35 pm - 8:50 pm
MDW
-
BOS
2h 15mnonstop
$156Southwest
Booking Insights

KAYAK's insights & trends for Boston to Midway flights

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 round-trip flights from Boston to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

For Boston to Chicago Midway Airport, Wednesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago Midway Airport back to Boston, the best deals are generally found on Tuesday, with Sunday being 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 round-trip 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 December, where tickets cost $137 (return) on average. On the other hand, the most expensive months are November and May, where the average cost of round-trip tickets is $406 and $301 respectively.

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

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 $257 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

To get a below average price on the flight from Boston to Chicago Midway Airport, you should book around 2 weeks before departure, which saves you about 38% 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 Boston to Midway

 
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.

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.

Good to know

Low seasonFebruary
Cheapest flight$68
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 2% 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 $68 for a one-way ticket and $135 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, American Airlines, Delta, and Alaska Airlines 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 Boeing 737-800 is the aircraft model that flies most regularly on the Boston to Chicago Midway Airport flight route.

  • Which airline alliances offer flights from Boston to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Boston and Chicago Midway Airport.

  • 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, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Boston to Chicago are Southwest and Delta. With an average price for the route of $273 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 $316 and an overall rating of 7.9.

  • 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.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $155 or less one-way and $275 or less round-trip.

Prefer to fly direct from Boston to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Boston Logan Intl to Chicago Midway.
Find which airlines fly direct from Boston Logan Intl Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct 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

Direct 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

Reviews of the top airlines flying from Boston to Midway

 
See real verified KAYAK customer reviews for airlines flying from Boston to Chicago. 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 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 verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4267 reviews
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

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

Other airlines flying to Boston

Flight deals from the most popular airlines with KAYAK users flying the route