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Cheap flights from Boston (BOS) to Midway (MDW) from $46

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 8/17. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
BOS — MDW
jun. 11 — jun. 181
From?
To?
mar. 6/11
mar. 6/18
1 adult, Economy
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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 junio 6, 2024.

Popular in

June

Cheapest in

December

Round-trip from

$223

One-way from

$46
High demand for flights, 20% potential price rise
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Best time to find cheap flights, 43% potential price drop
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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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What is the cheapest day to fly round-trip from Boston to Chicago Midway Airport?

Monday is generally a great day to depart. Flying on this day could help you save up to 70%.

How far in advance should I book a flight from Boston to Chicago Midway Airport?

To save on the cost of your flight from Boston to Chicago Midway Airport, book at least 52 days before your planned departure. Booking around this time can save you about 38% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $279 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $332.

What is the cheapest month to fly from Boston to Chicago Midway Airport?

Flights from Boston to Chicago Midway Airport lean towards being more expensive in June. Prices are generally better when you fly from Boston to Chicago Midway Airport in January, with the cheapest ticket starting at $106.

What is the cheapest time of day to fly from BOS to MDW?

Unlike at noon, when flights are generally more expensive, you can save up to 46% on flights from Boston to Chicago Midway Airport by exploring options for tickets in the morning.

Cheap Boston to Midway flights in June & July 2024

Find cheap flight options from Boston to Midway specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Prices were last updated on junio 6, 2024.
Scroll through some of the best deals on flights from Boston to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
mié. 6/127:49 amBOS - MDW
1 stop6h 43mFrontier
mar. 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 6/5$131
mar. 7/3010:58 amBOS - MDW
1 stop11h 27mFrontier
mar. 8/137:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/5$137
mar. 7/3010:58 amBOS - MDW
1 stop11h 27mFrontier
mar. 8/137:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/5$141
mar. 6/1112:36 pmBOS - MDW
1 stop9h 44mFrontier
mar. 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 6/5$143
jue. 7/1110:58 amBOS - MDW
1 stop10h 11mFrontier
dom. 7/149:04 pmMDW - BOS
1 stop10h 22mFrontier
Deal found 6/6$151
jue. 7/1110:58 amBOS - MDW
1 stop10h 11mFrontier
dom. 7/149:04 pmMDW - BOS
1 stop10h 22mFrontier
Deal found 6/5$152
mié. 7/176:00 amBOS - MDW
1 stop8h 34mFrontier
mié. 7/242:29 pmMDW - BOS
1 stop8h 58mFrontier
Deal found 6/5$157
vie. 7/59:38 amBOS - MDW
1 stop14h 20mFrontier
vie. 7/122:23 pmMDW - BOS
1 stop9h 04mFrontier
Deal found 6/5$158
mié. 7/106:00 amBOS - MDW
1 stop8h 34mFrontier
dom. 7/149:04 pmMDW - BOS
1 stop10h 22mFrontier
Deal found 6/6$159

Boston to Midway 2024 flight deals

Discover exclusive flight deals for travel between Boston and Midway in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated junio 6, 2024.
Scroll through some of the best deals on flights from Boston to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
mié. 8/149:16 amBOS - MDW
1 stop13h 39mFrontier
mar. 8/207:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/6$96
mar. 8/2712:36 pmBOS - MDW
1 stop7h 37mFrontier
sáb. 8/317:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/5$99
vie. 9/612:36 pmBOS - MDW
1 stop7h 37mFrontier
lun. 9/97:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/5$106
mié. 8/289:16 amBOS - MDW
1 stop13h 39mFrontier
mar. 9/37:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/5$108
mié. 9/49:16 amBOS - MDW
1 stop13h 39mFrontier
lun. 9/97:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/4$113
mié. 8/149:16 amBOS - MDW
1 stop13h 39mFrontier
sáb. 8/247:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/5$114
vie. 9/139:16 amBOS - MDW
1 stop13h 39mFrontier
lun. 9/167:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/5$129
mié. 6/127:49 amBOS - MDW
1 stop6h 43mFrontier
mar. 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 6/5$131
vie. 8/29:26 amBOS - MDW
1 stop8h 39mFrontier
mar. 8/137:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/4$133

Boston to Midway flights leaving soon

Find last-minute flight options from Boston to Midway for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated junio 6, 2024.
Consider one of these great deals we found on last-minute flights from Boston to Chicago. Tip: verify your flight details before completing your reservation.
mié. 6/127:49 amBOS - MDW
1 stop6h 43mFrontier
mar. 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 6/5$131
mar. 6/1112:36 pmBOS - MDW
1 stop9h 44mFrontier
mar. 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 6/5$143
mié. 6/127:49 amBOS - MDW
1 stop6h 43mFrontier
vie. 6/146:11 pmMDW - BOS
1 stop13h 58mFrontier
Deal found 6/5$168
mar. 6/1112:36 pmBOS - MDW
1 stop9h 44mFrontier
vie. 6/146:11 pmMDW - BOS
1 stop13h 58mFrontier
Deal found 6/5$179
mié. 6/127:49 amBOS - MDW
1 stop6h 43mFrontier
mar. 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 6/6$182
mar. 6/1112:36 pmBOS - MDW
1 stop9h 44mFrontier
vie. 6/146:11 pmMDW - BOS
1 stop13h 58mFrontier
Deal found 6/6$187
mié. 6/127:49 amBOS - MDW
1 stop6h 43mFrontier
mar. 7/210:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 6/5$220
jue. 6/1312:22 pmBOS - MDW
1 stop8h 34mFrontier
mar. 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 6/5$229
jue. 6/1312:22 pmBOS - MDW
1 stop8h 34mFrontier
vie. 6/146:11 pmMDW - BOS
1 stop13h 58mFrontier
Deal found 6/6$237

One-way flights to Midway from Boston

Search for one-way flight options from Boston to Midway. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated junio 6, 2024.
Take a look at some of the best available options we've come across on one-way flights from Boston to Chicago. Users can also find round-trip Boston to Chicago flights by using the search form above.
sáb. 8/1712:48 pmBOS - MDW
1 stop7h 25mFrontier
Deal found 6/6$46
mié. 8/1412:36 pmBOS - MDW
1 stop7h 37mFrontier
Deal found 6/6$47
vie. 9/612:36 pmBOS - MDW
1 stop7h 37mFrontier
Deal found 6/5$50
mié. 8/289:16 amBOS - MDW
1 stop13h 39mFrontier
Deal found 6/5$64
mié. 9/49:16 amBOS - MDW
1 stop13h 39mFrontier
Deal found 6/5$69
sáb. 8/1712:48 pmBOS - MDW
1 stop7h 25mFrontier
Deal found 6/6$76
mié. 6/197:49 amBOS - MDW
1 stop6h 43mFrontier
Deal found 6/5$77
vie. 8/29:26 amBOS - MDW
1 stop8h 39mFrontier
Deal found 6/5$79
mié. 6/197:49 amBOS - MDW
1 stop6h 43mFrontier
Deal found 6/5$80

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 3,050,429 searches. Data last updated junio 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$96 - $314

Route

Depart

Return

Price

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

mié. 8/14

1 stop13h 39m

Chicago Midway

mar. 8/20

1 stop10h 26m

$96

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

mar. 8/27

1 stop7h 37m

Chicago Midway

sáb. 8/31

1 stop10h 26m

$99

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

mié. 8/21

1 stop7h 37m

Chicago Midway

mar. 8/27

1 stop10h 26m

$100

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

vie. 9/6

1 stop7h 37m

Chicago Midway

lun. 9/9

1 stop10h 26m

$106

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

mié. 8/28

1 stop13h 39m

Chicago Midway

mar. 9/3

1 stop10h 26m

$108

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

jue. 8/15

1 stop7h 37m

Chicago Midway

vie. 8/16

1 stop20h 05m

$111

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

mié. 9/4

1 stop13h 39m

Chicago Midway

lun. 9/9

1 stop10h 26m

$113

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

dom. 6/16

Nonstop2h 35m

Chicago Midway

sáb. 6/22

2 stops6h 30m

$260

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

dom. 6/16

1 stop4h 28m

Chicago Midway

mar. 6/18

1 stop5h 25m

$314

Flights are sorted by cheapest first

Deals found on 6/6

What is the cheapest day to fly from Boston to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Boston to Midway. Price data was last updated on June 2, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Boston to Chicago Midway Airport flight should consider departing on Tuesday mornings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

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.

Temperature and rainfall in Midway by month

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

CHI

Temperature

23 - 73.4 °F

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 junio 6, 2024.
Peruse reviews from past customers who have flown with Delta, Frontier and Porter Airlines 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
8.2
Very good
5,918 reviews

Entertainment

7.8

Overall

8.2

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.2
Very good
5,918 reviews
Southwest
8.2
Very good
5,918 reviews

Entertainment

7.8

Overall

8.2

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Delta
8.0
Very good
10,368 reviews
Southwest
8.2
Very good
5,918 reviews

Entertainment

7.8

Overall

8.2

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Allegiant Air
7.5
Good
994 reviews
Southwest
8.2
Very good
5,918 reviews

Entertainment

7.8

Overall

8.2

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Porter Airlines
7.4
Good
382 reviews
Southwest
8.2
Very good
5,918 reviews

Entertainment

7.8

Overall

8.2

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Frontier
6.2
Okay
3,985 reviews
Southwest
8.2
Very good
5,918 reviews

Entertainment

7.8

Overall

8.2

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

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 4 flights from Logan Intl to Chicago Midway per day from 4 different airlines.

  • Can I find flights from Boston to Chicago Midway Airport for under $100 on Cheapflights?

    Yes, there are multiple flights from Boston to Chicago Midway Airport for under $100. The cheapest flight booked recently is on Frontier for just $96, but on average you can expect to pay $129.

  • Are there nonstop flights from Boston to Chicago Midway Airport for under $300 on Cheapflights?

    Cheapflights has at least 1 direct flight from Boston to Chicago Midway Airport under $300. A good price for a nonstop flight from Boston to Chicago Midway Airport is less than $246.

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

    There are currently 20+ open flights from Boston to Chicago Midway Airport within the next 7 days for less than $200.

  • What is the cheapest airline to fly from Boston to Chicago Midway Airport round-trip?

    According to our current data, Frontier ($96), offers the cheapest pricing from Boston to Chicago Midway Airport. You may be able to fly from Boston to Chicago Midway Airport for 72% less than the average price by searching for this airline.

  • 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 6/6.

  • What are the most popular airlines that fly from Boston to Chicago Midway Airport?

    When booking a flight from Boston to Chicago Midway Airport, you may want to consider flying on American Airlines, Delta or Frontier as they are the most popular for this route.

  • What is the cheapest month to book a flight from Boston to Chicago Midway Airport?

    Currently, December is the cheapest month in which you can book a flight from Boston to Chicago Midway Airport (average of $141). Flying from Boston to Chicago Midway Airport in July 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.

See more FAQs

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Alternative routes for Boston to Midway
See prices for flight routes from nearby airports that may be better suited for you.

Boston to O'Hare Intl flights
Hartford to O'Hare Intl flights
Hartford to Midway flights
Albany to O'Hare Intl flights
Albany to Midway flights
Boston to Rockford flights
Worcester to O'Hare Intl flights
West Tisbury to O'Hare Intl flights
Hyannis to O'Hare Intl flights
Nantucket to O'Hare Intl flights
Hartford to Rockford flights
Provincetown to O'Hare Intl flights
New Bedford to O'Hare Intl flights

Top 4 airlines flying from Boston to Midway

Discover the top 4 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 3,050,429 searches. Data last updated junio 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$89Average$326FlexibilityNo cancel feeOn-time69%
FrontierCheapest$97Average$151FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$126Average$252FlexibilityNo cancel feeOn-time71%
DeltaCheapest$315Average$462FlexibilityNo cancel feeOn-timeN/A
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Search flights from Boston to Midway by cabin class

Find flights from Boston to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from Boston to Midway

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 junio 6, 2024.
12%of flight departuresEarly morningMidnight to 6 am
24%of flight departuresMorning6 am to noon
41%of flight departuresAfternoonNoon to 6 pm
23%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Boston to Midway

Explore weekly flight availability from Boston to Midway. 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 junio 6, 2024.
Sunday3daily flights
Monday5daily flights
Tuesday4daily flights
Wednesday4daily flights
Thursday5daily flights
Friday5daily flights
Saturday2daily flights

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