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$76+ Cheap flights from Midway (MDW) to Boston (BOS)

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 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Apr 29 — May 61
Wed 4/29
Wed 5/6
1 adult, Economy
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Find cheap flights from Midway to Boston with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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Cheapflights Tip: The best prices from Chicago Midway to Boston Logan Intl are usually found in July or June, booked 35 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

Cheap flight deals from Midway to Boston

Cheapest flights from Midway to Boston
Explore the most affordable flight options available from Midway to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 30, 2026.

This Southwest deal was found by Cheapflights users on 3/26. 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 5/57:45 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Wed 5/62:25 pm
BOS
-
MDW
Nonstop2h 40m
Southwest
Deal found 3/26$135
This Southwest deal was found by Cheapflights users on 3/25. 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 4/147:45 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Tue 4/142:25 pm
BOS
-
MDW
Nonstop2h 40m
Southwest
Deal found 3/25$137
This Frontier deal was found by Cheapflights users on 3/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/212:15 pm
MDW
-
BOS
1 stop10h 16m
Frontier
Fri 5/112:42 pm
BOS
-
MDW
1 stop7h 49m
Frontier
Deal found 3/25$140
This Southwest deal was found by Cheapflights users on 3/26. 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 4/217:45 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Wed 4/225:45 am
BOS
-
MDW
1 stop6h 50m
Southwest
Deal found 3/26$145
This Southwest deal was found by Cheapflights users on 3/26. 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 4/213:15 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Fri 4/2410:40 am
BOS
-
MDW
Nonstop2h 40m
Southwest
Deal found 3/26$146
This CheapOair deal was found by Cheapflights users on 3/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/202:15 pm
MDW
-
BOS
1 stop10h 16m
Frontier
Sat 5/211:16 am
BOS
-
MDW
1 stop21h 25m
Frontier
Deal found 3/27$151
This Southwest deal was found by Cheapflights users on 3/24. 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 4/217:45 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Mon 4/276:45 pm
BOS
-
MDW
1 stop5h 00m
Southwest
Deal found 3/24$155
This Southwest deal was found by Cheapflights users on 3/26. 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 4/1111:25 am
MDW
-
BOS
Nonstop2h 20m
Southwest
Wed 4/1510:45 am
BOS
-
MDW
Nonstop2h 40m
Southwest
Deal found 3/26$157

Find flight deals from Midway to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Boston (BOS). 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 March 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$135
(Southwest)

One-way from

$76
(Expedia)

Popular in

January

Cheapest in

July

Average price

$273

Good round-trip deal

$167 or less

Good one-way deal

$108 or less
Provider with most accurate pricing for Chicago Midway-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Boston Logan Intl flights.
Search Deals
From Chicago Midway to Boston Logan Intl
Search Deals
One-way flight from Chicago Midway to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Boston Logan Intl.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Boston Logan Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Boston 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 March 30, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 4/8

3:15 pm-6:35 pm

Nonstop2h 20m

Boston Logan Intl

Wed 5/13

6:00 pm-10:15 pm

1 stop5h 15m

$180

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 4/28

6:00 pm-9:20 pm

Nonstop2h 20m

Boston Logan Intl

Tue 5/5

6:20 pm-8:10 pm

Nonstop2h 50m

$181

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 4/10

7:00 pm-10:20 pm

Nonstop2h 20m

Boston Logan Intl

Sun 4/12

6:10 am-7:55 am

Nonstop2h 45m

$181
Quickest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 6/21

5:15 am-8:25 am

Nonstop2h 10m

Boston Logan Intl

Wed 6/24

5:35 am-7:10 am

Nonstop2h 35m

$197

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 6/21

5:15 am-8:25 am

Nonstop2h 10m

Boston Logan Intl

Fri 6/26

5:25 am-7:00 am

Nonstop2h 35m

$231

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 4/30

9:00 am-4:05 pm

1 stop6h 05m

Boston Logan Intl

Mon 5/4

7:10 am-9:00 am

Nonstop2h 50m

$240

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 4/11

7:45 am-3:50 pm

1 stop7h 05m

Boston Logan Intl

Sun 4/12

6:10 am-7:55 am

Nonstop2h 45m

$241

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 5/27

12:50 pm-7:40 pm

2 stops5h 50m

Boston Logan Intl

Mon 6/1

5:30 am-1:10 pm

2 stops8h 40m

$270

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 4/16

7:40 am-10:55 am

Nonstop2h 15m

Boston Logan Intl

Mon 4/20

5:50 pm-11:55 pm

1 stop7h 05m

$271

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 5/15

6:36 pm-11:29 pm

1 stop3h 53m

Boston Logan Intl

Sat 5/16

5:40 am-8:43 am

1 stop4h 03m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Midway to Boston

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 Midway to Boston in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*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 Chicago Midway Airport-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Boston 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 Chicago Midway Airport-Boston 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 Midway to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Midway 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 Chicago Midway Airport to Boston

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

Use this chart to determine the optimal time to book a round-trip flight from Midway to Boston. Price data was last updated on March 13, 2026.

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Boston, you should look to book at least 35 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Boston (average of $92). Flying from Chicago Midway Airport to Boston in August is currently the most expensive (average of $182). 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 MDW to BOS?

Find hourly flight availability from Midway to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 30, 2026.

It’s optimal to fly from Chicago Midway Airport to Boston in the afternoon. By choosing this option you can save up to 11% on the cost of your flight, compared to a flight at noon.

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

Use this chart to determine the cheapest time to fly round-trip from Midway to Boston. Price data was last updated on March 28, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Boston flight should consider departing on Friday afternoons 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.

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

The best insider tips for Chicago Midway Airport to Boston 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 Chicago Midway Airport to Boston 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 Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated March 30, 2026.
Get a feel of what it's like to fly with Southwest from Chicago Midway Airport to Boston by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,329 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Overall

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
8.0
Very good
4,329 reviews
Southwest
8.0
Very good
4,329 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Overall

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 Midway to Boston. 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 into for flights to Boston from Chicago Midway?

    Most people fly into Boston Logan Intl (BOS) if they book a flight to Boston from Chicago Midway. On average, Logan Intl has 2 inbound flights from Chicago Midway per day from 1 airline. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

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

    A quick flight from Chicago Midway Airport to Boston can take about 2h 20m. Southwest provides one of the quickest options available for as low as $180. Chicago Midway Airport and Boston are separated by a distance of 857 mi. Most flights are nonstop.

  • What is the cheapest airline to fly from Chicago Midway Airport to Boston round-trip?

    Currently priced at $124, Southwest will fly you from Chicago Midway Airport to Boston and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Southwest is 57% cheaper than the average price of flights available within the next 90 days to this destination.

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

    The cheapest flight price from Chicago Midway Airport to Boston is $72. On average you can expect to pay $247. The most popular route, (Chicago Midway - Boston Logan Intl), can usually be booked for $135.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Boston 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 Chicago Midway Airport to Boston?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Boston (average of $92). Flying from Chicago Midway Airport to Boston in August is currently the most expensive (average of $182). 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 Boston?

Book flights to Boston if you plan to visit one of these locations
Medford
Cambridge
Concord
Hampton Beach
Watertown
Brockton
Seekonk
Seabrook
Cranston
Chelsea
Lincoln
Warwick
Peabody
Waltham
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy
Lowell

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top airline flying from Midway to Boston

Discover the top airline that operate flights from Midway to Boston. 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 March 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$124Average$284FlexibilityNo cancel feeOn-time63%

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