BOS - MDW

$96 Find Cheap Flights from Boston to Chicago Midway Airport - Compare and Save

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 6/30. 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 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
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$182
Typical prices: $354-$197
Southwest
Tue 7/21Tue 7/28
BOS - MDW • Non-stop
Cheapest non-stop
$182
Typical prices: $374-$205
Southwest
Tue 7/21Tue 7/21
BOS - MDW • Non-stop
Top airlines
Cheapest • from $182 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 40m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $182 (round-trip)
Shortest trip • 4h 29m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 27% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 49% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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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

Tue, Jul 21 - Tue, Jul 28
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
7:40 am - 10:55 am
MDW
-
BOS
2h 15mnonstop
$182Southwest
Thu, Sep 17 - Sat, Sep 19
Southwest Logo
8:20 pm - 10:00 pm
BOS
-
MDW
2h 40mnonstop
Southwest Logo
7:40 am - 11:00 am
MDW
-
BOS
2h 20mnonstop
$183Southwest
Mon, Aug 17 - Sat, Aug 22
Southwest Logo
8:20 pm - 10:00 pm
BOS
-
MDW
2h 40mnonstop
Southwest Logo
11:25 am - 2:45 pm
MDW
-
BOS
2h 20mnonstop
$184Southwest
Tue, Jun 30 - Sat, Jul 4
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
12:50 pm - 8:25 pm
MDW
-
BOS
6h 35m
2 stops
$185Southwest
Thu, Jul 16 - Mon, Jul 20
Southwest Logo
7:30 am - 9:10 am
BOS
-
MDW
2h 40mnonstop
Southwest Logo
7:35 pm - 10:55 pm
MDW
-
BOS
2h 20mnonstop
$187Southwest
Wed, Aug 12 - Fri, Aug 14
Southwest Logo
7:15 pm - 8:50 pm
BOS
-
MDW
2h 35mnonstop
Southwest Logo
5:45 am - 9:00 am
MDW
-
BOS
2h 15mnonstop
$188Southwest
Wed, Jul 15 - Fri, Jul 17
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
6:00 pm - 11:30 pm
MDW
-
BOS
4h 30m
1 stop
$189Southwest
Thu, Jul 30 - Thu, Aug 13
Southwest Logo
5:25 am - 7:00 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
5:45 am - 9:00 am
MDW
-
BOS
2h 15mnonstop
$190Southwest
Wed, Jul 1 - Tue, Jul 7
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
9:00 am - 12:15 pm
MDW
-
BOS
2h 15mnonstop
$191Southwest
Wed, Jul 8 - Wed, Jul 15
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
5:30 pm - 11:25 pm
MDW
-
BOS
4h 55m
1 stop
$192Southwest
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.

How much is a round-trip flight from Boston to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Boston to Chicago Midway Airport departing in July.

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, Thursday 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 Saturday, 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 October, where the average cost of round-trip tickets is $406 and $335 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 $280 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 27% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 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 seasonMarch
Cheapest flight$96
Best time to beat the crowds but there is an average 17% increase in price.
Most popular time to fly and prices are also 3% lower on average.
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 5 days, the lowest price for a flight from Boston to Chicago Midway Airport was $96 for a one-way ticket and $182 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?

    American Airlines, JetBlue, 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 $281 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $385 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 $183 or less one-way and $266 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 3 airlines serving 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.
7.9
SouthwestOverall score based on 4237 reviews
8.0Comfort
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

I like everything. Blythe at DCA is the absolute best!

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

They lost my luggage and refuse to help. Terrible airline. I've never experienced worse customer service in my life. Pretty much just told me too bad that I lost all my luggage, not caring that I am stuck in Europe for 2 weeks with absolutely nothing.

You should have had Wifi to make it much enjoyable.

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

The flight was delayed after already taxiing from the gate due to a malfunction. After 3 hours we were told the flight was canceled. The next flight available was Sunday. My daughter and I stayed overnight in the airport due to this issue. I was given a $12 meal voucher. Unacceptable

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

Nice plane, clean, wifi available and movies. All the flight attendants were courteous.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

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