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Midway

$64+ Cheap flights from Boston (BOS) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Boston Logan Intl to Chicago Midway are usually found in December or January, booked 85 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

Cheap flight deals from Boston to Midway

Cheapest flights from Boston to Midway
Explore the most affordable flight options available from Boston to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Southwest deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:35 pmBOS - MDW
1 stop4h 30mSouthwest
Tue 1/62:35 pmMDW - BOS
1 stop6h 10mSouthwest
Deal found 12/21$212
This Southwest deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:35 pmBOS - MDW
1 stop4h 30mSouthwest
Fri 1/211:45 amMDW - BOS
1 stop6h 50mSouthwest
Deal found 12/21$242
This Southwest deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:35 pmBOS - MDW
1 stop4h 30mSouthwest
Thu 1/16:35 amMDW - BOS
1 stop5h 55mSouthwest
Deal found 12/22$266
This Expedia deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:03 amBOS - MDW
1 stop7h 35mFrontier
Wed 12/313:10 pmMDW - BOS
1 stop17h 42mFrontier
Deal found 12/22$293
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:09 amBOS - MDW
1 stop12h 03mFrontier
Mon 1/53:10 pmMDW - BOS
2 stops33h 09mFrontier
Deal found 12/22$295
This Southwest deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:20 pmBOS - MDW
1 stop6h 30mSouthwest
Fri 1/29:40 pmMDW - BOS
1 stop9h 35mSouthwest
Deal found 12/22$302

Find flight deals from Boston to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$127
(Southwest)

One-way from

$64
(Southwest)

Popular in

November

Cheapest in

December

Average price

$177

Good round-trip deal

$333 or less

Good one-way deal

$166 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago Midway flights.
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From Boston Logan Intl to Chicago Midway
Search Deals
One-way flight from Boston Logan Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Chicago Midway.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 23, 2025.
Use the filters below to find and compare flights from Boston to Chicago Midway Airport that are best for you.

Fly from

Boston

Fly to

Midway

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/10

7:10 am-11:35 am

1 stop5h 25m

Chicago Midway

Thu 1/15

6:35 pm-9:50 pm

Nonstop2h 15m

$141

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 1/26

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Tue 1/27

1:50 pm-9:25 pm

1 stop6h 35m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 2/24

5:50 am-11:35 am

1 stop6h 45m

Chicago Midway

Fri 2/27

6:05 am-9:25 am

Nonstop2h 20m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/17

7:10 am-11:35 am

1 stop5h 25m

Chicago Midway

Tue 1/20

2:35 pm-9:45 pm

1 stop6h 10m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 1/14

2:40 pm-4:30 pm

Nonstop2h 50m

Chicago Midway

Wed 1/21

2:00 pm-5:10 pm

Nonstop2h 10m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 3/9

6:25 pm-8:25 pm

Nonstop3h 00m

Chicago Midway

Thu 3/12

7:55 am-11:10 am

Nonstop2h 15m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 1/26

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Mon 2/2

2:00 pm-5:10 pm

Nonstop2h 10m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/9

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sun 1/11

12:30 pm-10:10 pm

1 stop8h 40m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 2/9

5:20 am-7:10 am

Nonstop2h 50m

Chicago Midway

Tue 2/10

2:00 pm-5:10 pm

Nonstop2h 10m

$162

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 2/12

9:00 am-1:50 pm

1 stop5h 50m

Chicago Midway

Sat 2/14

6:10 pm-9:25 pm

Nonstop2h 15m

$162

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 21 results
1
2
3

Compare providers for flights from Boston to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Midway in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Boston-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Boston-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Boston-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Boston-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Boston to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Boston with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Boston to Chicago Midway Airport

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

Use this chart to determine the optimal time to book a round-trip flight from Boston to Midway. Price data was last updated on December 19, 2025.

The price you pay for your flight from Boston to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 84 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Boston to Chicago Midway Airport?

Currently, June is the cheapest month in which you can book a flight from Boston to Chicago Midway Airport (average of $97). Flying from Boston to Chicago Midway Airport in April is currently the most expensive (average of $176). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from BOS to MDW?

Find hourly flight availability from Boston to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 23% on flights from Boston to Chicago Midway Airport by exploring options for tickets in the evening.

What is the cheapest day to fly from Boston to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Boston to Midway. Price data was last updated on December 20, 2025.

Travelers seeking maximum savings on their Boston to Chicago Midway Airport flight should consider departing on Wednesday at noon when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Boston to Chicago Midway Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Boston to Chicago Midway Airport trip
Airports
BOS

Use the FlyLogan App to pre-order meals at BOS, saving time before your flight to MDW.

Read more about BOSBy Paul Rubio
MDW

Take the Orange Line train from MDW to downtown Chicago in under 30 minutes for a quick city transfer.

Read more about MDWBy Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Paul Rubio

Paul Rubio

Expert on BOS

Paul Rubio

Paul Rubio

Travel journalist and photographer Paul Rubio is a Miami native (and current resident), who has lived in nine countries and traveled to 137. He is an expert in luxury travel, eco-travel, loyalty programs, hotels, airports and airlines. He is a contributing editor at AFAR, Condé Nast Traveler, LUXURY Magazine, and Palm Beach Illustrated.

Read more

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated December 23, 2025.
Peruse reviews from past customers who have flown with Southwest and Delta from Boston to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,014 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Boston to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Boston to Chicago Midway?

    If you book a flight to Chicago Midway from Boston, you will be flying from Logan Intl, which is the city’s only airport. Boston Logan Intl (BOS) is located 2.6 mi from the center of Boston. There are 2 flights from Logan Intl to Chicago Midway per day from 2 different airlines.

  • How long is the flight from Boston to Chicago Midway Airport?

    Southwest can get you from Boston to Chicago Midway Airport in just under 5h 25m. Your travel time can differ by up to . Boston and Chicago Midway Airport are separated by a distance of 857 mi.

  • What are the cheapest airlines flying from Boston to Chicago Midway Airport round-trip?

    According to our current data, Southwest ($117), and Delta ($207) offers the cheapest pricing from Boston to Chicago Midway Airport. You may be able to fly from Boston to Chicago Midway Airport for 54% less than the average price by searching for these airlines.

  • What are the cheapest flights from Boston to Chicago Midway Airport?

    Looking for the cheapest flight from Boston to Chicago Midway Airport? While on average our users pay $348, our data indicates the cheapest price to be $73. The most popular route (Boston Logan Intl - Chicago Midway), is priced around $137.

  • Can I find deals for flights from Boston to Midway that include hotel bookings?

    Yes. In addition to deals on Boston to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Midway.

  • Can I find deals for business class flights from Boston to Midway?

    Yes. Cheapflights offers flight deals from Boston to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Boston to Chicago Midway Airport?

    Currently, June is the cheapest month in which you can book a flight from Boston to Chicago Midway Airport (average of $97). Flying from Boston to Chicago Midway Airport in April is currently the most expensive (average of $176). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Boston to Midway

Discover the top 2 airlines that operate flights from Boston to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$117Average$270FlexibilityNo cancel feeOn-time63%
DeltaCheapest$207Average$316FlexibilityNo cancel feeOn-timeN/A

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