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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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Chicago Midway are usually found in January or June, booked 85 days in advance, depart on a Wednesday or Tuesday and return on a Saturday

Cheap 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 September 16, 2025.

Round-trip from

$123
(Southwest)

One-way from

$64
(Southwest)

Popular in

November

Cheapest in

January

Average price

$218

Good round-trip deal

$210 or less

Good one-way deal

$171 or less
From Boston Logan Intl to Chicago Midway
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One-way flight from Boston Logan Intl to Chicago Midway
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Highest demand for flights based on searches. 5% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Boston Logan Intl to Chicago Midway.
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Price to beat on a one-way flight from Boston Logan Intl to Chicago Midway.
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Find 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 September 16, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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.
Tue 11/115:35 pmBOS - MDW
1 stop4h 30mSouthwest
Fri 11/147:15 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/15$123
This Southwest deal was found by Cheapflights users on 9/15. 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 10/25:35 amBOS - MDW
1 stop5h 40mSouthwest
Mon 10/66:05 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/15$127
This Southwest deal was found by Cheapflights users on 9/15. 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 10/305:15 amBOS - MDW
Nonstop2h 40mSouthwest
Sun 11/25:45 amMDW - BOS
1 stop10h 25mSouthwest
Deal found 9/15$133
This Southwest deal was found by Cheapflights users on 9/15. 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.
Fri 11/146:50 pmBOS - MDW
1 stop5h 40mSouthwest
Sun 11/165:00 amMDW - BOS
1 stop6h 50mSouthwest
Deal found 9/15$137
This Southwest deal was found by Cheapflights users on 9/15. 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.
Tue 11/45:35 pmBOS - MDW
1 stop4h 30mSouthwest
Fri 11/79:30 amMDW - BOS
2 stops7h 45mSouthwest
Deal found 9/15$138
This Southwest deal was found by Cheapflights users on 9/15. 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 10/307:15 amBOS - MDW
2 stops7h 05mSouthwest
Tue 11/49:20 amMDW - BOS
1 stop6h 15mSouthwest
Deal found 9/15$142
This Southwest deal was found by Cheapflights users on 9/15. 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 12/35:35 pmBOS - MDW
1 stop4h 30mSouthwest
Sun 12/79:35 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/15$143
This Southwest deal was found by Cheapflights users on 9/16. 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.
Sat 11/225:25 amBOS - MDW
Nonstop2h 45mSouthwest
Fri 11/285:00 amMDW - BOS
1 stop6h 50mSouthwest
Deal found 9/16$147
This Southwest deal was found by Cheapflights users on 9/14. 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.
Sat 11/225:25 amBOS - MDW
Nonstop2h 45mSouthwest
Wed 12/38:25 amMDW - BOS
2 stops7h 10mSouthwest
Deal found 9/14$152
This Southwest deal was found by Cheapflights users on 9/16. 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 9/258:35 amBOS - MDW
Nonstop2h 35mSouthwest
Mon 9/298:35 pmMDW - BOS
1 stop10h 35mSouthwest
Deal found 9/16$153

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 September 16, 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 10/25

10:30 am-12:10 pm

Nonstop2h 40m

Chicago Midway

Tue 10/28

6:10 am-1:15 pm

1 stop6h 05m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/2

5:35 am-10:15 am

1 stop5h 40m

Chicago Midway

Mon 10/6

5:50 pm-9:05 pm

Nonstop2h 15m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/31

5:15 am-10:40 am

1 stop6h 25m

Chicago Midway

Mon 11/3

6:40 am-12:55 pm

1 stop5h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 12/5

1:35 pm-3:20 pm

Nonstop2h 45m

Chicago Midway

Sun 12/7

7:15 pm-10:30 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 11/22

5:25 am-7:10 am

Nonstop2h 45m

Chicago Midway

Fri 11/28

2:55 pm-11:15 pm

1 stop7h 20m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/8

5:30 pm-10:05 pm

1 stop5h 35m

Chicago Midway

Sun 1/11

9:40 am-12:55 pm

Nonstop2h 15m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 2/19

5:20 am-7:10 am

Nonstop2h 50m

$69

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 2/10

2:40 pm-4:30 pm

Nonstop2h 50m

$69

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 10/21

5:05 pm-12:05 am

1 stop8h 00m

$69

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 2/4

5:30 am-7:20 am

Nonstop2h 50m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 16 results
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The best insider tips for Boston to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-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.
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

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 September 12, 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, April is the cheapest month in which you can book a flight from Boston to Chicago Midway Airport (average of $160). Flying from Boston to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 16, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 7% on flights from Boston to Chicago Midway Airport by exploring options for tickets at noon.

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 September 14, 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. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 September 16, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines 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
4,242 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 3 flights from Logan Intl to Chicago Midway per day from 4 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 2h 40m. Your travel time will be generally consistent. Boston and Chicago Midway Airport are separated by a distance of 857 mi. Generally, flights for this route are nonstop.

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

    According to our current data, United Airlines ($97), Frontier ($100), and Southwest ($120) offers the cheapest pricing from Boston to Chicago Midway Airport. You may be able to fly from Boston to Chicago Midway Airport for 61% 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 $278, our data indicates the cheapest price to be $68. The most popular route (Boston Logan Intl - Chicago Midway), is priced around $117.

  • 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, April is the cheapest month in which you can book a flight from Boston to Chicago Midway Airport (average of $160). Flying from Boston to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Top 4 airlines flying from Boston to Midway

Discover the top 4 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$97Average$177FlexibilityNo cancel feeOn-time69%
FrontierCheapest$100Average$103FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$120Average$268FlexibilityNo cancel feeOn-time63%
DeltaCheapest$227Average$346FlexibilityNo cancel feeOn-timeN/A

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