Midway

$74+ 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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Nov 5 — Nov 121
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The best prices from Boston Logan Intl to Chicago Midway are usually found in September or January, booked 45 days in advance, depart on a Tuesday or Thursday and return on a Wednesday

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 October 31, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

June

Cheapest in

September

Round-trip from

$110
(Frontier)

One-way from

$74
(Frontier)
Provider with most accurate pricing for Boston Logan Intl-Chicago Midway flight deals.
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago Midway flights.
High demand for flights, 32% potential price rise
Best time to find cheap flights, 30% potential price drop
From Boston Logan Intl to Chicago Midway
One-way flight from Boston Logan Intl to Chicago Midway

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 October 31, 2024.

This Frontier deal was found by Cheapflights users on 10/30. 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.
Mon 11/1811:24 amBOS - MDW
1 stop11h 50mFrontier
Wed 11/275:35 pmMDW - BOS
1 stop5h 56mFrontier
Deal found 10/30$110
This Southwest deal was found by Cheapflights users on 10/30. 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 12/136:40 amBOS - MDW
Nonstop2h 45mSouthwest
Sun 12/158:30 pmMDW - BOS
Nonstop2h 10mSouthwest
Deal found 10/30$124
This eDestinos deal was found by Cheapflights users on 10/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/157:31 pmBOS - MDW
2 stops29h 25mMultiple Airlines
Mon 11/186:51 pmMDW - BOS
1 stop27h 30mMultiple Airlines
Deal found 10/30$172

Find flights from Boston to Midway within your budget

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 2,570,725 searches. Data last updated October 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 11/25

11:35 am-9:59 pm

1 stop11h 24m

$74

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/10

8:10 am-10:05 am

Nonstop2h 55m

$79

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 11/13

7:31 pm-5:09 pm

1 stop22h 38m

$92

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 1/27

6:05 am-5:10 pm

2 stops12h 05m

$142

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 12/27

4:15 pm-10:30 am

2 stops19h 15m

$296

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 11/18

11:24 am-10:14 pm

1 stop11h 50m

Chicago Midway

Wed 11/27

5:35 pm-12:31 am

1 stop5h 56m

$110

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 12/13

6:40 am-8:25 am

Nonstop2h 45m

Chicago Midway

Sun 12/15

8:30 pm-11:40 pm

Nonstop2h 10m

$124

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 11/15

7:31 pm-11:56 pm

2 stops29h 25m

Chicago Midway

Mon 11/18

6:51 pm-11:21 pm

1 stop27h 30m

$172

Flights are sorted by cheapest first

Deals found on 10/31

Compare providers for flights from Boston to Midway

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 Boston to Midway in October.
ProviderPrice AccuracyTrust Score*Cancellation Policy
ExpediaPrice Accuracy1 starTrust Score*3 starsCancellation PolicyAirline Policy
FlightHubPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
eDreamsPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy

*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 Boston-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Boston-Chicago Midway Airport 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 Boston-Chicago Midway Airport 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 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.

Travel insights for flights from Boston to Midway

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

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 October 25, 2024.

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 45 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 $159). Flying from Boston to Chicago Midway Airport in July is currently the most expensive (average of $231). 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 October 31, 2024.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 14% on flights from Boston to Chicago Midway Airport by exploring options for tickets in the morning.

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, 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 23.0 F).

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 October 31, 2024.
Peruse reviews from past customers who have flown with Southwest, Delta and Frontier from Boston to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
5,116 reviews

Crew

8.7

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.3

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

8.1
Very good
5,116 reviews
8.1
Very good
5,116 reviews

Crew

8.7

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.3

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

8.0
Very good
8,835 reviews
8.1
Very good
5,116 reviews

Crew

8.7

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.3

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

7.8
Good
294 reviews
8.1
Very good
5,116 reviews

Crew

8.7

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.3

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

6.1
Okay
3,580 reviews
8.1
Very good
5,116 reviews

Crew

8.7

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Boarding

8.3

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 2 flights from Logan Intl to Chicago Midway per day from 6 different airlines.

  • Can I find flights from Boston to Chicago Midway Airport for under $200 on Cheapflights?

    Yes, there are multiple flights from Boston to Chicago Midway Airport for under $200. The cheapest flight booked recently is on Frontier for just $110, but on average you can expect to pay $178.

  • Are there nonstop flights from Boston to Chicago Midway Airport for under $200 on Cheapflights?

    Cheapflights has at least 1 direct flight from Boston to Chicago Midway Airport under $200. A good price for a nonstop flight from Boston to Chicago Midway Airport is less than $118.

  • Are there last-minute flights available from Boston to Chicago Midway Airport for under $200?

    There are currently 3+ open flights from Boston to Chicago Midway Airport within the next 7 days for less than $200.

  • What days are nonstop flights available from Boston to Chicago Midway Airport?

    Nonstop flights are available for this route on the following days: Sunday, Monday, Tuesday, Thursday, Friday.

  • How many flights depart from Boston to Chicago Midway Airport on average per day?

    Travelers can expect 11 flights from Boston to Chicago Midway Airport on average per day.
    Early Morning (Midnight to 6am) - 18% of flight departures
    Morning (6am - Noon) - 27% of flight departures
    Afternoon (Noon - 6pm) - 27% of flight departures
    Evening (6pm - Midnight) - 27% of flight departures

  • How long is the flight from Boston to Chicago Midway Airport?

    Frontier, Southwest, and Delta can get you from Boston to Chicago Midway Airport in just under 2h 50m. Your travel time can differ by up to 9h. Boston and Chicago Midway Airport are separated by a distance of 863 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, Frontier ($110), Southwest ($118), and Delta ($312) offers the cheapest pricing from Boston to Chicago Midway Airport. You may be able to fly from Boston to Chicago Midway Airport for 63% 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 Frontier ($74), Southwest ($79), and Delta ($142).

  • 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 $295, our data indicates the cheapest price to be $79. The most popular route (Boston Logan Intl - Chicago Midway), is priced around $113.

  • What does BOS to MDW mean?

    These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Boston Logan Intl Airport to Chicago Midway Airport flight would often be abbreviated as a BOS to MDW flight.

  • Can I find deals for flights from Boston to Midway that include extra baggage allowance?

    The amount of baggage you can bring on your Boston to Midway flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Boston to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Boston to Midway flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Boston to Midway that allow pets onboard?

    Many airlines flying from Boston to Midway offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Boston to Midway?

    Yes, you can often find last-minute deals on Boston to Midway flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Boston to Chicago Midway Airport flight deals updated?

    The Boston to Chicago Midway Airport flight deals you see on this page were last updated on 10/30.

  • 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 $159). Flying from Boston to Chicago Midway Airport in July is currently the most expensive (average of $231). 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.

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Top 6 airlines flying from Boston to Midway

Discover the top 6 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 2,570,725 searches. Data last updated October 31, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$76Average$102FlexibilityNo cancel feeOn-time65%
FrontierCheapest$98Average$147FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$126Average$238FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$144Average$220FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$147Average$336FlexibilityNo cancel feeOn-time69%
DeltaCheapest$315Average$447FlexibilityNo cancel feeOn-timeN/A
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