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$79+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Jan 8 — Jan 151
Wed 1/8
Wed 1/15
1 adult, Economy
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The best prices from Boston Logan Intl to Chicago Midway are usually found in January or September, 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 January 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

June

Cheapest in

January

Average price

$158
Provider with most accurate pricing for Boston Logan Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago Midway flights.
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From Boston Logan Intl to Chicago Midway
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One-way flight from Boston Logan Intl to Chicago Midway
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High demand for flights, 22% potential price rise
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Best time to find cheap flights, 4% potential price drop
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Average for round-trip flights in January 2025
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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 January 3, 2025.

This Southwest deal was found by Cheapflights users on 1/2. 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.
Thu 1/235:40 pmBOS - MDW
Nonstop2h 50mSouthwest
Sun 1/268:40 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 1/2$157
This Frontier deal was found by Cheapflights users on 1/2. 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.
Thu 2/206:00 amBOS - MDW
1 stop14h 29mFrontier
Mon 2/247:25 pmMDW - BOS
1 stop14h 08mFrontier
Deal found 1/2$158
This Lucky2Go deal was found by Cheapflights users on 1/3. 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/245:35 pmBOS - MDW
2 stops30h 54mMultiple Airlines
Sun 1/267:25 amMDW - BOS
1 stop25h 09mMultiple Airlines
Deal found 1/3$172
This Delta deal was found by Cheapflights users on 1/3. 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 1/175:20 amBOS - MDW
1 stop4h 34mDelta
Wed 1/222:08 pmMDW - BOS
1 stop8h 34mDelta
Deal found 1/3$300

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 2,558,603 searches. Data last updated January 3, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/23

5:40 pm-7:30 pm

Nonstop2h 50m

Chicago Midway

Sun 1/26

8:40 am-11:55 am

Nonstop2h 15m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 2/20

6:00 am-7:29 pm

1 stop14h 29m

Chicago Midway

Mon 2/24

7:25 pm-10:33 am

1 stop14h 08m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/24

5:35 pm-11:29 pm

2 stops30h 54m

Chicago Midway

Sun 1/26

7:25 am-9:34 am

1 stop25h 09m

$172

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/17

5:20 am-8:54 am

1 stop4h 34m

Chicago Midway

Wed 1/22

2:08 pm-11:42 pm

1 stop8h 34m

$300

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 2/5

8:10 am-10:05 am

Nonstop2h 55m

$79

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 2/12

6:00 am-11:00 pm

1 stop18h 00m

$80

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 2/26

6:00 am-3:13 pm

2 stops34h 13m

$99

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sun 3/9

5:30 am-8:45 am

1 stop4h 15m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/3

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 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 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 December 27, 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 $160). Flying from Boston to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 January 3, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 20% 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 January 3, 2025.
Peruse reviews from past customers who have flown with Southwest 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.
Southwest
8.1
Very good
4,688 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

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
4,688 reviews
Southwest
8.1
Very good
4,688 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

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
8,527 reviews
Southwest
8.1
Very good
4,688 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

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
3,452 reviews
Southwest
8.1
Very good
4,688 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

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 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 is 1 flight from Logan Intl to Chicago Midway per day from 5 different airlines.

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

    According to our current data, Southwest ($157), Frontier ($158), and Delta ($300) offers the cheapest pricing from Boston to Chicago Midway Airport. You may be able to fly from Boston to Chicago Midway Airport for 47% 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 Southwest ($79), Frontier ($80), and Delta ($159).

  • 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 $357, our data indicates the cheapest price to be $79. The most popular route (Boston Logan Intl - Chicago Midway), is priced around $141.

  • 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.

  • 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 $160). Flying from Boston to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 5 airlines flying from Boston to Midway

Discover the top 5 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 2,558,603 searches. Data last updated January 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$76Average$102FlexibilityNo cancel feeOn-time65%
FrontierCheapest$100Average$150FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$147Average$336FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$148Average$239FlexibilityNo cancel feeOn-time63%
DeltaCheapest$315Average$439FlexibilityNo cancel feeOn-timeN/A
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