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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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Feb 1 — Feb 81
Sat 2/1
Sat 2/8
1 adult, Economy
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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 January 27, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$153
(FlightHub)

One-way from

$79
(Southwest)

Popular in

June

Cheapest in

February

Average price

$208

Good round-trip deal

$194 or less

Good one-way deal

$108 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. 16% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 27, 2025.

This FlightHub deal was found by Cheapflights users on 1/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/81:19 pmMDW - BOS
1 stop10h 46mFrontier
Sun 5/1112:48 pmBOS - MDW
1 stop11h 51mFrontier
Deal found 1/27$153
This Southwest deal was found by Cheapflights users on 1/26. 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.
Wed 2/1910:05 amMDW - BOS
Nonstop2h 15mSouthwest
Sun 2/236:50 amBOS - MDW
Nonstop2h 55mSouthwest
Deal found 1/26$157
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/146:42 pmMDW - BOS
1 stop4h 09mDelta
Mon 3/175:30 amBOS - MDW
1 stop4h 15mDelta
Deal found 1/27$317

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 January 27, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 3/7

2:41 pm-8:21 am

1 stop16h 40m

Boston Logan Intl

Mon 3/10

5:10 am-11:34 am

1 stop7h 24m

$154

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 2/16

8:20 pm-11:35 pm

Nonstop2h 15m

Boston Logan Intl

Tue 2/18

6:35 pm-8:25 pm

Nonstop2h 50m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 3/14

2:55 pm-7:54 pm

1 stop3h 59m

Boston Logan Intl

Mon 3/17

5:30 am-8:45 am

1 stop4h 15m

$317

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 2/26

10:05 am-1:20 pm

Nonstop2h 15m

$79

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 3/4

8:30 am-12:44 am

1 stop15h 14m

$80

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 5/30

8:04 pm-9:12 am

1 stop12h 08m

$140

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 5/25

5:59 pm-11:02 pm

1 stop4h 03m

$160

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 5/12

8:35 am-12:14 pm

3 stops26h 39m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 starsTrust 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.

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 January 27, 2025.

It’s optimal to fly from Chicago Midway Airport to Boston in the afternoon. By choosing this option you can save up to 32% 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 January 26, 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 evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago Midway Airport to Boston

Explore weekly flight availability from Midway to Boston. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 27, 2025.

The most flights from MDW to BOS are scheduled on a Saturday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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 January 27, 2025.
See what other customers who have flown with Frontier, Southwest and Delta 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
4,608 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,608 reviews
Southwest
8.1
Very good
4,608 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,468 reviews
Southwest
8.1
Very good
4,608 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
795 reviews
Southwest
8.1
Very good
4,608 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,432 reviews
Southwest
8.1
Very good
4,608 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 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 $153, Frontier will fly you from Chicago Midway Airport to Boston and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Southwest and Delta - these airlines can fly you to your destination from $157 and $317, respectively. Frontier is 46% 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 Frontier and Delta, with prices starting from $80 and $159, 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 $208. The most popular route, (Chicago Midway - Boston Logan Intl), can usually be booked for $157.

  • 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
Sturbridge
Warwick
Marlborough
Waltham
Brockton
Cambridge
Watertown
Framingham
Somerville
Chestnut Hill
Seekonk
Randolph
Lowell
West Yarmouth
Woburn
Saco
Seabrook
Salem
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 January 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$63Average$394FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$86Average$122FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$153Average$284FlexibilityNo cancel feeOn-time63%
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