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$59+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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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”

2. Select your favorite providers

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3. Compare prices and book

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Cheapflights Tip: The best prices from Chicago Midway to Boston Logan Intl are usually found in January or March, 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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Southwest)

One-way from

$68
(Southwest)

Popular in

February

Cheapest in

January

Average price

$293

Good round-trip deal

$179 or less

Good one-way deal

$78 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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High demand for flights, 12% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 17, 2025.

This Southwest deal was found by Cheapflights users on 4/16. 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 5/27:20 pmMDW - BOS
Nonstop2h 15mSouthwest
Sun 5/47:40 amBOS - MDW
Nonstop2h 35mSouthwest
Deal found 4/16$117
This CheapOair deal was found by Cheapflights users on 4/16. 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.
Thu 5/84:00 pmMDW - BOS
1 stop16h 34mFrontier
Wed 5/148:00 amBOS - MDW
1 stop29h 24mFrontier
Deal found 4/16$191
This Mytrip deal was found by Cheapflights users on 4/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/68:36 pmMDW - BOS
1 stop11h 36mAllegiant Air
Sun 6/811:31 amBOS - MDW
1 stop20h 44mAllegiant Air
Deal found 4/17$211
This Delta deal was found by Cheapflights users on 4/16. 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.
Wed 5/146:25 pmMDW - BOS
1 stop4h 21mDelta
Wed 5/285:20 amBOS - MDW
1 stop8h 08mDelta
Deal found 4/16$295

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 April 17, 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

Fri 5/2

7:20 pm-10:35 pm

Nonstop2h 15m

Boston Logan Intl

Sun 5/4

7:40 am-9:15 am

Nonstop2h 35m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 5/8

4:00 pm-9:34 am

1 stop16h 34m

Boston Logan Intl

Wed 5/14

8:00 am-12:24 pm

1 stop29h 24m

$191

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 6/6

8:36 pm-9:12 am

1 stop11h 36m

Boston Logan Intl

Sun 6/8

11:31 am-7:15 am

1 stop20h 44m

$211

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 5/14

6:25 pm-11:46 pm

1 stop4h 21m

Boston Logan Intl

Wed 5/28

5:20 am-12:28 pm

1 stop8h 08m

$295

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 5/30

8:04 pm-8:41 am

3 stops35h 37m

Boston Logan Intl

Mon 6/2

6:00 am-7:14 pm

3 stops14h 14m

$410

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 5/6

6:25 pm-9:45 pm

Nonstop2h 20m

$59

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 7/2

9:03 am-10:41 am

1 stop24h 38m

$96

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 5/16

1:19 pm-12:44 am

1 stop10h 25m

$102

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 6/2

8:04 pm-11:29 pm

2 stops26h 25m

$140

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 5/14

6:00 am-3:14 pm

1 stop8h 14m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 eDreams the most. eDreams 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 April 11, 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 April 17, 2025.

It’s optimal to fly from Chicago Midway Airport to Boston in the afternoon. By choosing this option you can save up to 23% 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 30, 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. Monday 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 April 17, 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
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,916 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 4 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 $117, 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 Frontier and Allegiant Air - these airlines can fly you to your destination from $191 and $211, respectively. Southwest is 58% 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?

    $68 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Allegiant Air and Frontier, with prices starting from $96 and $105, respectively.

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

    The cheapest flight price from Chicago Midway Airport to Boston is $48. On average you can expect to pay $219. The most popular route, (Chicago Midway - Boston Logan Intl), can usually be booked for $117.

  • 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
Marlborough
Warwick
Waltham
Framingham
Cambridge
Chestnut Hill
Seekonk
Randolph
Brockton
Lowell
Seabrook
West Yarmouth
Woburn
Somerville
Saco
Burlington
Smithfield
Lincoln
Salem
Chelsea

Browse thousands of different options on Cheapflights for your next trip

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Top 4 airlines flying from Midway to Boston

Discover the top 4 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$63Average$366FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$86Average$116FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$157Average$297FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$292FlexibilityNo cancel feeOn-time63%

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