BOS - MDW

$69 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 9/22. 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

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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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

Thu, Oct 2 - Mon, Oct 6
Southwest Logo
5:35 am - 10:15 amBOS-MDW
5h 40m1 stop
Southwest Logo
9:20 pm - 12:40 amMDW-BOS
2h 20mnonstop
$127Southwest
Find Deal
Thu, Oct 2 - Mon, Oct 6
Southwest Logo
5:35 am - 1:20 pmBOS-MDW
8h 45m2 stops
Southwest Logo
5:50 pm - 9:05 pmMDW-BOS
2h 15mnonstop
$132Southwest
Find Deal
Thu, Oct 30 - Sun, Nov 2
Southwest Logo
5:15 am - 6:55 amBOS-MDW
2h 40mnonstop
Southwest Logo
9:10 am - 6:10 pmMDW-BOS
8h 00m1 stop
$133Southwest
Find Deal
Sat, Sep 20 - Sun, Sep 21
Southwest Logo
5:50 am - 7:25 amBOS-MDW
2h 35mnonstop
Southwest Logo
5:55 am - 9:10 amMDW-BOS
2h 15mnonstop
$137Southwest
Find Deal
Wed, Nov 12 - Wed, Nov 19
Southwest Logo
5:35 pm - 9:05 pmBOS-MDW
4h 30m1 stop
Southwest Logo
2:30 pm - 10:15 pmMDW-BOS
6h 45m2 stops
$138Southwest
Find Deal
Thu, Oct 30 - Mon, Nov 3
Southwest Logo
7:15 am - 1:20 pmBOS-MDW
7h 05m2 stops
Southwest Logo
6:40 am - 12:55 pmMDW-BOS
5h 15m1 stop
$142Southwest
Find Deal
Thu, Oct 30 - Sun, Nov 2
Frontier Logo
10:04 am - 6:39 pmBOS-MDW
9h 35m1 stop
Frontier Logo
10:12 am - 8:28 amMDW-BOS
21h 16m1 stop
$155Frontier
Find Deal
Wed, Dec 10 - Mon, Dec 15
Frontier Logo
6:00 am - 9:32 pmBOS-MDW
16h 32m1 stop
Frontier Logo
6:00 am - 12:44 amMDW-BOS
17h 44m1 stop
$160Frontier
Find Deal
Thu, Dec 11 - Mon, Dec 15
Frontier Logo
6:00 am - 11:05 pmBOS-MDW
18h 05m1 stop
Frontier Logo
6:00 am - 12:44 amMDW-BOS
17h 44m1 stop
$161Frontier
Find Deal
Thu, Oct 30 - Mon, Nov 3
 Logo
9:39 am - 2:33 pmBOS-MDW
5h 54m1 stop
 Logo
1:37 pm - 11:16 amMDW-BOS
20h 39m2 stops

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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 $127 (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 21% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 21% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$127
Overall average: $234
Southwest
Thu 10/2Mon 10/6
BOS - MDW • 1 stop
Cheapest non-stop
$137
Typical prices: $188-328
Southwest
Fri 9/26Sun 9/28
BOS - MDW • Non-stop
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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!
Expert advice

Expert advice for your flight from Boston to Midway

 
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
BOS

Use the FlyLogan app for gate info, flight status, and ordering ahead at restaurants. Reserve parking in advance during busy travel times.

Read more about BOSby Blane Bachelor
MDW

Take the CTA Orange Line from MDW to downtown Chicago in about 25-30 minutes, avoiding traffic and ensuring a smooth arrival.

Read more about MDWby Stefanie Waldek
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
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 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 January, where tickets cost $200 (return) on average. On the other hand, the most expensive months are November and March, where the average cost of round-trip tickets is $345 and $302 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.

No, with an average price for the route of $206, prices are generally cheapest when you fly direct.

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 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$69
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 9% 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 3 days, the lowest price for a flight from Boston to Chicago Midway Airport was $69 for a one-way ticket and $127 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, Alaska Airlines, and Hawaiian 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.

  • 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 $262 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 $346 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 $168 or less one-way and $192 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 4 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.
8.0
SouthwestOverall score based on 4242 reviews
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

Tastless food and too obvious lack of enthusiasm for service in the economy vesus business class

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

The service was good, the food could have been better.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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

Information on your arrival and departure airports

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