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Midway

$94+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Jun 23 — Jun 301
Tue 6/23
Tue 6/30
1 adult, Economy
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Find cheap flights from Boston to Midway with Cheapflights

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 31 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

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 May 24, 2026.

This Southwest deal was found by Cheapflights users on 5/19. 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 6/37:20 am
BOS
-
MDW
Nonstop2h 45m
Southwest
Tue 6/92:40 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 5/19$187
This Southwest deal was found by Cheapflights users on 5/20. 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 6/37:20 am
BOS
-
MDW
Nonstop2h 45m
Southwest
Sat 6/65:25 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Deal found 5/20$192
This Kiwi.com deal was found by Cheapflights users on 5/19. 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.
Tue 6/99:10 am
BOS
-
MDW
1 stop14h 01m
Frontier
Wed 6/106:00 am
MDW
-
BOS
1 stop18h 27m
Frontier
Deal found 5/19$193
This Southwest deal was found by Cheapflights users on 5/20. 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 6/103:45 pm
BOS
-
MDW
Nonstop2h 45m
Southwest
Fri 6/127:35 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Deal found 5/20$196
This Southwest deal was found by Cheapflights users on 5/20. 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 6/45:25 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Sun 6/75:15 am
MDW
-
BOS
Nonstop2h 10m
Southwest
Deal found 5/20$197
This Southwest deal was found by Cheapflights users on 5/20. 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 8/117:30 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Fri 8/145:45 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Deal found 5/20$201
This Southwest deal was found by Cheapflights users on 5/19. 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 6/310:45 am
BOS
-
MDW
Nonstop2h 40m
Southwest
Fri 6/55:20 pm
MDW
-
BOS
1 stop5h 45m
Southwest
Deal found 5/19$202
This Southwest deal was found by Cheapflights users on 5/20. 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 7/105:25 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Sun 7/125:15 am
MDW
-
BOS
Nonstop2h 10m
Southwest
Deal found 5/20$205
This Southwest deal was found by Cheapflights users on 5/20. 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 6/92:25 pm
BOS
-
MDW
1 stop4h 30m
Southwest
Fri 6/127:35 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Deal found 5/20$206
This Southwest deal was found by Cheapflights users on 5/20. 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 6/65:20 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Sat 6/135:45 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 5/20$207

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 May 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$187
(Southwest)

One-way from

$94
(Southwest)

Popular in

November

Cheapest in

December

Average price

$302

Good round-trip deal

$266 or less

Good one-way deal

$159 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago Midway flights.
Search Deals
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. 8% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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.
Search Deals

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 May 24, 2026.
Use the filters below to find and compare flights from Boston to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 7/21

5:35 am-7:10 am

Nonstop2h 35m

Chicago Midway

Fri 7/24

7:35 pm-10:50 pm

Nonstop2h 15m

$201

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 8/3

5:25 am-7:00 am

Nonstop2h 35m

Chicago Midway

Thu 8/6

8:15 am-4:10 pm

2 stops6h 55m

$220

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 7/28

5:35 am-7:10 am

Nonstop2h 35m

Chicago Midway

Sat 8/1

5:25 am-8:40 am

Nonstop2h 15m

$227

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 6/6

9:20 am-5:05 pm

1 stop8h 45m

Chicago Midway

Mon 6/8

7:35 pm-10:50 pm

Nonstop2h 15m

$233

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 5/27

8:10 am-3:45 pm

2 stops8h 35m

Chicago Midway

Thu 5/28

2:10 pm-11:55 pm

2 stops8h 45m

$235

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 5/27

8:10 am-3:45 pm

2 stops8h 35m

Chicago Midway

Wed 5/27

6:00 pm-9:20 pm

Nonstop2h 20m

$246

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 8/10

5:00 am-12:15 pm

1 stop8h 15m

Chicago Midway

Thu 8/20

6:30 pm-9:50 pm

Nonstop2h 20m

$247

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 8/15

5:50 am-10:40 am

1 stop5h 50m

Chicago Midway

Fri 8/21

5:45 am-9:00 am

Nonstop2h 15m

$251

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sun 7/5

7:20 am-9:00 am

Nonstop2h 40m

Chicago Midway

Thu 7/9

7:35 pm-10:50 pm

Nonstop2h 15m

$261

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 5/28

5:30 am-1:10 pm

2 stops8h 40m

Chicago Midway

Thu 5/28

3:50 pm-11:15 pm

1 stop6h 25m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/21

Showing 1-10 of 24 resultsSorted by cheapest first
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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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?

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 30 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, December is the cheapest month in which you can book a flight from Boston to Chicago Midway Airport (average of $137). Flying from Boston to Chicago Midway Airport in November is currently the most expensive (average of $406). 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 May 24, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 27% 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 May 16, 2026.

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

How much does it cost to fly round-trip from Boston to Chicago Midway Airport?

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
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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

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 May 24, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andJetBlue 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
7.9
Good
4,275 reviews

Crew

8.6

Overall

7.9

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,275 reviews
Southwest
7.9
Good
4,275 reviews

Crew

8.6

Overall

7.9

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,440 reviews
Southwest
7.9
Good
4,275 reviews

Crew

8.6

Overall

7.9

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,983 reviews
Southwest
7.9
Good
4,275 reviews

Crew

8.6

Overall

7.9

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 3 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 35m. 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, Delta ($88), JetBlue ($117), and Southwest ($128) offers the cheapest pricing from Boston to Chicago Midway Airport. You may be able to fly from Boston to Chicago Midway Airport for 67% 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 $291, our data indicates the cheapest price to be $102. The most popular route (Boston Logan Intl - Chicago Midway), is priced around $197.

  • 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, December is the cheapest month in which you can book a flight from Boston to Chicago Midway Airport (average of $137). Flying from Boston to Chicago Midway Airport in November is currently the most expensive (average of $406). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Boston to Midway

Discover the top 3 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 May 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$88Average$385FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$117Average$175FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$129Average$282FlexibilityNo cancel feeOn-time63%

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