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$69+ 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
ago 19 — ago 261
ter 8/19
ter 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Boston Logan Intl are usually found in January or March, booked 49 days in advance, depart on a Saturday or Wednesday and return on a Wednesday

Cheap 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 agosto 14, 2025.

Round-trip from

$137
(Southwest)

One-way from

$69
(Southwest)

Popular in

February

Cheapest in

January

Average price

$247

Good round-trip deal

$137 or less

Good one-way deal

$68 or less
From Chicago Midway to Boston Logan Intl
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One-way flight from Chicago Midway to Boston Logan Intl
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High demand for flights, 10% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago Midway to Boston Logan Intl.
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Price to beat on a one-way flight from Chicago Midway to Boston Logan Intl.
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Find 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 agosto 14, 2025.

This Southwest deal was found by Cheapflights users on 8/14. 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.
qua 9/36:25 amMDW - BOS
1 stop8h 00mSouthwest
sex 9/58:20 pmBOS - MDW
Nonstop2h 35mSouthwest
Deal found 8/14$133
This Southwest deal was found by Cheapflights users on 8/14. 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.
seg 9/156:45 pmMDW - BOS
Nonstop2h 20mSouthwest
qui 9/185:15 amBOS - MDW
Nonstop2h 30mSouthwest
Deal found 8/14$137
This Southwest deal was found by Cheapflights users on 8/14. 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.
sex 9/51:45 pmMDW - BOS
2 stops7h 30mSouthwest
seg 9/88:20 pmBOS - MDW
Nonstop2h 35mSouthwest
Deal found 8/14$142
This Southwest deal was found by Cheapflights users on 8/14. 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.
qua 9/36:25 amMDW - BOS
1 stop8h 00mSouthwest
qua 9/105:40 pmBOS - MDW
Nonstop2h 40mSouthwest
Deal found 8/14$143
This Southwest deal was found by Cheapflights users on 8/14. 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.
ter 9/1611:45 amMDW - BOS
1 stop4h 20mSouthwest
dom 9/215:30 amBOS - MDW
Nonstop2h 35mSouthwest
Deal found 8/14$147
This Southwest deal was found by Cheapflights users on 8/14. 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.
sáb 9/1311:40 amMDW - BOS
1 stop4h 40mSouthwest
sáb 9/201:10 pmBOS - MDW
1 stop4h 30mSouthwest
Deal found 8/14$157
This Southwest deal was found by Cheapflights users on 8/13. 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.
seg 9/86:45 amMDW - BOS
Nonstop2h 15mSouthwest
seg 9/298:20 pmBOS - MDW
Nonstop2h 35mSouthwest
Deal found 8/13$158
This Southwest deal was found by Cheapflights users on 8/14. 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.
seg 9/152:35 pmMDW - BOS
1 stop7h 25mSouthwest
seg 9/225:35 amBOS - MDW
2 stops8h 35mSouthwest
Deal found 8/14$162
This Southwest deal was found by Cheapflights users on 8/13. 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.
sex 9/56:45 pmMDW - BOS
Nonstop2h 20mSouthwest
dom 9/75:15 amBOS - MDW
1 stop5h 15mSouthwest
Deal found 8/13$168

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 agosto 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Boston that are best for you.

Fly from

Midway

Fly to

Boston

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

seg 9/8

4:45 pm-8:05 pm

Nonstop2h 20m

Boston Logan Intl

qua 9/10

9:25 am-11:05 am

Nonstop2h 40m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

qui 9/11

6:45 am-10:00 am

Nonstop2h 15m

Boston Logan Intl

qui 9/18

5:15 am-6:45 am

Nonstop2h 30m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

seg 9/15

6:45 pm-10:05 pm

Nonstop2h 20m

Boston Logan Intl

seg 9/22

8:20 pm-9:55 pm

Nonstop2h 35m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

seg 9/15

6:45 am-10:00 am

Nonstop2h 15m

Boston Logan Intl

sex 9/19

5:15 am-6:45 am

Nonstop2h 30m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

dom 9/7

5:55 am-9:10 am

Nonstop2h 15m

Boston Logan Intl

qua 9/10

5:40 pm-7:20 pm

Nonstop2h 40m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

dom 10/26

9:05 pm-12:25 am

Nonstop2h 20m

Boston Logan Intl

qua 10/29

10:05 am-11:50 am

Nonstop2h 45m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

seg 9/15

6:45 pm-10:05 pm

Nonstop2h 20m

Boston Logan Intl

qui 9/18

5:15 am-6:45 am

Nonstop2h 30m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

sex 9/5

2:35 pm-11:00 pm

1 stop7h 25m

Boston Logan Intl

seg 9/8

8:20 pm-9:55 pm

Nonstop2h 35m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

sex 10/17

9:20 pm-12:40 am

Nonstop2h 20m

Boston Logan Intl

ter 10/21

5:15 am-6:55 am

Nonstop2h 40m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

qua 9/3

6:25 am-3:25 pm

1 stop8h 00m

Boston Logan Intl

qua 9/10

5:40 pm-7:20 pm

Nonstop2h 40m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 21 results
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The best insider tips for Chicago Midway Airport to Boston 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 Chicago Midway Airport to Boston trip
Airports
MDW

Use the airport’s mobile system to order food directly to your gate, saving time and ensuring you don't miss boarding.

Read more about MDWby Ramsey Qubein
BOS

Take the Silver Line 1 (SL1) bus for a free ride from BOS to South Station in downtown Boston.

Read more about BOSby Paul Rubio
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 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 August 8, 2025.

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Boston, you should look to book at least 49 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Boston (average of $218). Flying from Chicago Midway Airport to Boston in July is currently the most expensive (average of $311). 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 agosto 14, 2025.

It’s optimal to fly from Chicago Midway Airport to Boston in the afternoon. By choosing this option you can save up to 22% 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 August 10, 2025.

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

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 agosto 14, 2025.
Get a feel of what it's like to fly with Southwest and United Airlines 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
4,244 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 3 inbound flights from Chicago Midway per day from 2 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

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

    Currently priced at $153, 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. Check Cheapflights for deals on United Airlines for as low as $157. Southwest is 44% 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 $68. On average you can expect to pay $200. The most popular route, (Chicago Midway - Boston Logan Intl), can usually be booked for $99.

  • 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Boston (average of $218). Flying from Chicago Midway Airport to Boston in July is currently the most expensive (average of $311). 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
Cambridge
Medford
Watertown
Hampton Beach
Waltham
Seabrook
Lowell
Lincoln
Smithfield
Cranston
Chestnut Hill
Warwick
Peabody
Quincy
York Beach
Chelsea
Swansea
Saugus
Burlington
Braintree

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Midway to Boston

Discover the top 2 airlines 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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$153Average$285FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$157Average$297FlexibilityNo cancel feeOn-time69%

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