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$79+ 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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Mar 3 — Mar 101
Mon 3/3
Mon 3/10
1 adult, Economy
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The best prices from Chicago Midway to Boston Logan Intl are usually found in January or February, booked 21 days in advance, depart on a Saturday or Wednesday and return on a Thursday

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 February 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$151
(Southwest)

One-way from

$79
(Southwest)

Popular in

June

Cheapest in

January

Average price

$202

Good round-trip deal

$212 or less

Good one-way deal

$126 or less
Provider with most accurate pricing for Chicago Midway-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Boston Logan Intl flights.
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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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Highest demand for flights based on searches. 18% potential increase in price ($62 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 February 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 February 26, 2025.

This Southwest deal was found by Cheapflights users on 2/26. 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.
Fri 3/147:35 amMDW - BOS
Nonstop2h 15mSouthwest
Mon 3/246:30 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 2/26$151
This Delta deal was found by Cheapflights users on 2/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/242:55 pmMDW - BOS
1 stop3h 59mDelta
Mon 3/315:30 amBOS - MDW
1 stop4h 15mDelta
Deal found 2/26$167
This Frontier deal was found by Cheapflights users on 2/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/154:40 pmMDW - BOS
1 stop7h 04mFrontier
Mon 3/175:10 amBOS - MDW
1 stop7h 24mFrontier
Deal found 2/26$244

Find flights from Midway to Boston within your budget

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 February 26, 2025.

Fly from

Midway

Fly to

Boston

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 3/14

7:35 am-10:50 am

Nonstop2h 15m

Boston Logan Intl

Mon 3/24

6:30 am-8:15 am

Nonstop2h 45m

$151

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 3/24

2:55 pm-7:54 pm

1 stop3h 59m

Boston Logan Intl

Mon 3/31

5:30 am-8:45 am

1 stop4h 15m

$167

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 3/15

4:40 pm-12:44 am

1 stop7h 04m

Boston Logan Intl

Mon 3/17

5:10 am-11:34 am

1 stop7h 24m

$244

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 4/6

8:10 am-11:25 am

Nonstop2h 15m

$79

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 3/24

6:42 pm-11:51 pm

1 stop4h 09m

$84

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 4/13

2:19 pm-12:02 pm

1 stop20h 43m

$109

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 3/15

4:40 pm-12:44 am

1 stop7h 04m

$118

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 5/9

10:59 am-11:09 am

2 stops23h 10m

$151

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/26

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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 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.

Travel insights for flights from Midway to Boston

Get recent, data-driven insights about flights from Midway to Boston including ideal travel times, pricing trends, and more.

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 February 14, 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 21 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 February 26, 2025.

It’s optimal to fly from Chicago Midway Airport to Boston in the afternoon. By choosing this option you can save up to 26% 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 February 23, 2025.

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

Rainfall in Boston by month

Plan your trip to Boston by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Boston ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Boston when rainfall is around 3.1 in.

Temperature in Boston by month

Plan your trip to Boston by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Boston, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 February 26, 2025.
See what other customers who have flown with Southwest, Delta and Allegiant Air from Chicago to Boston have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,369 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Boarding

8.2

Crew

8.7

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Southwest
8.1
Very good
4,369 reviews
Southwest
8.1
Very good
4,369 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Boarding

8.2

Crew

8.7

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Delta
8.0
Very good
8,149 reviews
Southwest
8.1
Very good
4,369 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Boarding

8.2

Crew

8.7

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Allegiant Air
7.3
Good
759 reviews
Southwest
8.1
Very good
4,369 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Boarding

8.2

Crew

8.7

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Frontier
6.0
Okay
3,337 reviews
Southwest
8.1
Very good
4,369 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Boarding

8.2

Crew

8.7

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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 0 inbound flights from Chicago Midway per day from 3 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 $151, 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. Search Cheapflights for deals from Delta and Frontier - these airlines can fly you to your destination from $167 and $242, respectively. Southwest is 45% cheaper than the average price of flights available within the next 90 days to this destination.

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

    $79 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Delta and Allegiant Air, with prices starting from $84 and $109, respectively.

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

    The cheapest flight price from Chicago Midway Airport to Boston is $78. On average you can expect to pay $234. The most popular route, (Chicago Midway - Boston Logan Intl), can usually be booked for $145.

  • 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Warwick
Marlborough
Waltham
Brockton
Cambridge
Framingham
Somerville
Chestnut Hill
Seekonk
Randolph
Lowell
West Yarmouth
Woburn
Saco
Sturbridge
Salem
Seabrook
Burlington
Brookline
Fall River

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Top 3 airlines flying from Midway to Boston

Discover the top 3 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 February 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$63Average$366FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$86Average$116FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$157Average$286FlexibilityNo cancel feeOn-time63%
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