BOS - MDW

$109 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 9/23. 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

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Everything you should know

Cheapest round-trip
$217
Typical prices: $200-$455
Southwest
Wed 10/28Sat 10/31
BOS - MDW • Non-stop
Cheapest one-way
$109
Typical prices: $68-$198
Southwest
Wed 9/23
BOS - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 34m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top layover airports
Baltimore (BWI)
Cheapest • Avg $182 (round-trip)
Detroit (DTW)
Shortest trip • 4h 28m (one-way)
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 19% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
December
Cheapest • 51% price drop
April
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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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, Oct 28 - Sat, Oct 31
Southwest Logo
4:20 pm - 5:55 pm
BOS
-
MDW
2h 35mnonstop
Southwest Logo
8:15 am - 11:35 am
MDW
-
BOS
2h 20mnonstop
$217Southwest
Sat, Sep 19 - Tue, Sep 29
Southwest Logo
7:05 am - 8:40 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
6:40 am - 9:55 am
MDW
-
BOS
2h 15mnonstop
$217Southwest
Sat, Sep 26 - Tue, Sep 29
Southwest Logo
7:05 am - 8:40 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
8:45 am - 12:15 pm
MDW
-
BOS
2h 30mnonstop
$217Southwest
Wed, Sep 9 - Wed, Sep 16
Southwest Logo
3:20 pm - 4:55 pm
BOS
-
MDW
2h 35mnonstop
Southwest Logo
8:45 am - 12:15 pm
MDW
-
BOS
2h 30mnonstop
$217Southwest
Mon, Nov 2 - Fri, Nov 20
Delta Logo
9:45 pm - 9:17 am
BOS
-
MDW
12h 32m
2 stops
Delta Logo
6:44 pm - 11:56 pm
MDW
-
BOS
4h 12m
1 stop
$304Delta
Tue, Nov 3 - Fri, Nov 20
Delta Logo
6:05 am - 6:00 pm
BOS
-
MDW
12h 55m
2 stops
Delta Logo
6:44 pm - 11:56 pm
MDW
-
BOS
4h 12m
1 stop
$304Delta
Fri, Aug 14 - Mon, Aug 17
Delta Logo
1:10 pm - 6:33 pm
BOS
-
MDW
6h 23m
1 stop
Delta Logo
6:42 pm - 7:45 am
MDW
-
BOS
12h 03m
2 stops
$310Delta
Wed, Oct 21 - Fri, Oct 23
Multiple Airlines Logo
11:28 am - 9:58 pm
BOS
-
MDW
11h 30m
1 stop
Multiple Airlines Logo
2:26 pm - 9:29 am
MDW
-
BOS
18h 03m
2 stops
$385Multiple Airlines
Sat, Oct 10 - Mon, Oct 12
Multiple Airlines Logo
11:05 am - 9:58 pm
BOS
-
MDW
11h 53m
2 stops
Multiple Airlines Logo
1:26 pm - 10:42 am
MDW
-
BOS
20h 16m
1 stop
$403Multiple Airlines
Fri, Dec 11 - Fri, Dec 11
Frontier Logo
11:57 am - 7:02 pm
BOS
-
MDW
8h 05m
1 stop
Frontier Logo
9:23 pm - 8:40 am
MDW
-
BOS
10h 17m
1 stop
$405Frontier
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 September.

Flight prices are typical for this route right now.

Flights to Chicago Midway Airport from Boston usually cost between $208 and $403 in September.
The lowest price found in the past 5 days was $217 on Southwest (Sep 9-Sep 16).

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 Friday, 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 $400 and $356 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 19% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

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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.

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 season

March

Cheapest flight

$109
Best time to beat the crowds but there is an average 14% 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 5 days, the lowest price for a flight from Boston to Chicago Midway Airport was $109 for a one-way ticket and $217 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 MAX 8 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?

    oneworld, and SkyTeam are the airline alliances operating flights between Boston and Chicago Midway Airport, with oneworld being the most commonly used for this 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 $284 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 $385 and an overall rating of 7.8.

  • 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 $167 or less one-way and $238 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

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Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

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Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Boston Logan Intl

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

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Thursday

Southwest

Southwest

Friday

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Saturday

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Sunday

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See more direct flights

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
Southwest flights from Boston to Chicago Midway Airport