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$69+ 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 7/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 September, booked 84 days in advance, depart on a Wednesday or Thursday 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 July 3, 2025.

Round-trip from

$137
(Southwest)

One-way from

$69
(Southwest)

Popular in

March

Cheapest in

January

Average price

$259

Good round-trip deal

$137 or less

Good one-way deal

$139 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 ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/2. 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 7/105:15 amBOS - MDW
Nonstop2h 35mSouthwest
Tue 7/155:05 amMDW - BOS
Nonstop2h 10mSouthwest
Deal found 7/2$137
This Priceline deal was found by Cheapflights users on 7/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/169:40 amBOS - MDW
1 stop11h 42mFrontier
Sun 8/173:58 pmMDW - BOS
1 stop7h 40mFrontier
Deal found 7/2$149

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 July 3, 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

Tue 7/15

7:20 am-9:00 am

Nonstop2h 40m

Chicago Midway

Thu 7/17

8:05 am-11:20 am

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 8/16

9:40 am-8:22 pm

1 stop11h 42m

Chicago Midway

Sun 8/17

3:58 pm-12:38 am

1 stop7h 40m

$149

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 7/11

5:50 pm-7:40 pm

Nonstop2h 50m

$69

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 10/13

10:10 am-6:18 pm

1 stop9h 08m

$76

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 8/15

9:00 am-6:17 pm

1 stop10h 17m

$143

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sun 10/5

6:55 pm-4:33 pm

2 stops22h 38m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

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 June 27, 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 July 3, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 10% 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 June 29, 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.

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

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 July 3, 2025.
Peruse reviews from past customers who have flown with Southwest, Allegiant Air, and Frontier 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
4,266 reviews

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
708 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 5 different airlines.

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

    According to our current data, Southwest ($137), Frontier ($184), and Allegiant Air ($229) offers the cheapest pricing from Boston to Chicago Midway Airport. You may be able to fly from Boston to Chicago Midway Airport for 46% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Boston to Chicago Midway Airport one-way?

    The cheapest airlines for a one-way flight from Boston to Chicago Midway Airport are Southwest ($69), Frontier ($76), and Allegiant Air ($100).

  • 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 $239, our data indicates the cheapest price to be $68. 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, 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 Boston?

Book flights to Boston if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Top 5 airlines flying from Boston to Midway

Discover the top 5 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$97Average$187FlexibilityNo cancel feeOn-time69%
FrontierCheapest$100Average$118FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$124Average$255FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$187Average$259FlexibilityNo cancel feeOn-time71%
DeltaCheapest$227Average$386FlexibilityNo cancel feeOn-timeN/A

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