HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Boston

$76+ 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
abr. 2 — abr. 91
mié. 4/2
mié. 4/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Boston with Cheapflights

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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago Midway to Boston Logan Intl are usually found in January or September, 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 marzo 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$157
(Southwest)

One-way from

$76
(Southwest)

Popular in

February

Cheapest in

January

Average price

$272

Good round-trip deal

$201 or less

Good one-way deal

$88 or less
Provider with most accurate pricing for Chicago Midway-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Boston Logan Intl flights.
Search Deals
From Chicago Midway to Boston Logan Intl
Search Deals
One-way flight from Chicago Midway to Boston Logan Intl
Search Deals
High demand for flights, 7% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Boston Logan Intl.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Boston Logan Intl.
Search Deals

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 marzo 28, 2025.

This Southwest deal was found by Cheapflights users on 3/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/105:30 amMDW - BOS
Nonstop2h 15mSouthwest
lun. 4/145:45 amBOS - MDW
Nonstop2h 35mSouthwest
Deal found 3/27$157
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/151:19 pmMDW - BOS
1 stop10h 46mFrontier
dom. 5/1810:14 amBOS - MDW
1 stop13h 26mFrontier
Deal found 3/27$198
This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/308:04 pmMDW - BOS
1 stop12h 08mAllegiant Air
dom. 6/111:31 amBOS - MDW
1 stop27h 55mAllegiant Air
Deal found 3/27$235
This Delta deal was found by Cheapflights users on 3/27. 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.
mié. 4/161:16 pmMDW - BOS
1 stop5h 14mDelta
mié. 4/235:30 amBOS - MDW
1 stop8h 05mDelta
Deal found 3/27$285
This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/238:04 pmMDW - BOS
1 stop12h 08mMultiple Airlines
lun. 5/265:45 amBOS - MDW
2 stops14h 29mMultiple Airlines
Deal found 3/27$391

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 marzo 28, 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

jue. 4/10

5:30 am-8:45 am

Nonstop2h 15m

Boston Logan Intl

lun. 4/14

5:45 am-7:20 am

Nonstop2h 35m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

jue. 5/15

1:19 pm-1:05 am

1 stop10h 46m

Boston Logan Intl

dom. 5/18

10:14 am-10:40 pm

1 stop13h 26m

$198

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

vie. 5/30

8:04 pm-9:12 am

1 stop12h 08m

Boston Logan Intl

dom. 6/1

11:31 am-2:26 pm

1 stop27h 55m

$235

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

mié. 4/16

1:16 pm-7:30 pm

1 stop5h 14m

Boston Logan Intl

mié. 4/23

5:30 am-12:35 pm

1 stop8h 05m

$285

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

vie. 5/23

8:04 pm-9:12 am

1 stop12h 08m

Boston Logan Intl

lun. 5/26

5:45 am-7:14 pm

2 stops14h 29m

$391

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

mié. 6/4

4:20 pm-10:25 pm

1 stop5h 05m

$76

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

jue. 4/3

2:24 pm-11:32 am

1 stop20h 08m

$99

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

jue. 4/17

12:46 pm-12:47 am

1 stop11h 01m

$105

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

mié. 4/16

9:52 am-11:34 pm

2 stops12h 42m

$153

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

vie. 6/6

8:36 pm-11:47 pm

2 stops26h 11m

$169

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

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 March.
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.

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 March 21, 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 marzo 28, 2025.

It’s optimal to fly from Chicago Midway Airport to Boston in the afternoon. By choosing this option you can save up to 24% 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 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. Tuesday evenings 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 marzo 28, 2025.
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

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
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

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
7,897 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

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
731 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

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
3,271 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

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 1 inbound flight 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 $157, 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 $198 and $235, respectively. Southwest is 43% 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?

    $76 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 $99 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 $73. On average you can expect to pay $210. The most popular route, (Chicago Midway - Boston Logan Intl), can usually be booked for $97.

  • 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
Cambridge
Framingham
Chestnut Hill
Seekonk
Randolph
Brockton
Lowell
West Yarmouth
Woburn
Somerville
Saco
Burlington
Smithfield
Salem
Chelsea
Seabrook
Brookline

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 marzo 28, 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$291FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.