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Cheap flights from Boston (BOS) to Midway (MDW) from $58

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 6/5. 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 2 — Jun 91
From?
To?
Sun 6/2
Sun 6/9
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 May 28, 2024.

Popular in

June

Cheapest in

December

Round-trip from

$222

One-way from

$58
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 $328.

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.

When is the cheapest time to fly from Boston to Chicago Midway Airport (BOS - MDW)?

Unlike at noon, when flights are generally more expensive, you can save up to 41% on flights from Boston to Chicago Midway Airport by exploring options for tickets in the morning.

Cheap Southwest flights from Boston to Midway

Explore cheap flight options specifically provided by Southwest for the route between Boston and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,740,132 searches. Data last updated May 28, 2024.
Find some of the cheapest Southwest flights traveling from Boston to Chicago. Be sure to come back soon if the deals available don't appeal to you at this time.
Thu 6/136:30 amBOS - MDW
Nonstop2h 35mSouthwest
Fri 6/149:05 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 5/28$216
Sun 6/166:30 amBOS - MDW
Nonstop2h 35mSouthwest
Sat 6/224:10 pmMDW - BOS
2 stops6h 30mSouthwest
Deal found 5/27$232
Thu 6/136:30 amBOS - MDW
Nonstop2h 35mSouthwest
Fri 6/149:15 amMDW - BOS
2 stops8h 45mSouthwest
Deal found 5/28$244
Thu 6/137:10 amBOS - MDW
2 stops10h 55mSouthwest
Fri 6/144:25 pmMDW - BOS
1 stop7h 35mSouthwest
Deal found 5/28$263
Thu 6/137:10 amBOS - MDW
2 stops10h 55mSouthwest
Fri 6/1410:45 pmMDW - BOS
2 stops15h 55mSouthwest
Deal found 5/28$282
Sun 6/168:10 pmBOS - MDW
1 stop5h 10mSouthwest
Sat 6/224:10 pmMDW - BOS
2 stops6h 30mSouthwest
Deal found 5/27$346

Cheap Delta flights from Boston to Midway

Explore cheap flight options specifically provided by Delta for the route between Boston and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,740,132 searches. Data last updated May 28, 2024.
Some of the best deals we've found on Delta flights traveling from Boston to Chicago. Ensure the flight price, dates, time, and airline match your criteria before you book.
Sat 6/155:20 amBOS - MDW
1 stop4h 28mDelta
Sat 6/155:45 pmMDW - BOS
1 stop5h 11mDelta
Deal found 5/28$314
Sat 9/77:10 amBOS - MDW
1 stop5h 34mDelta
Mon 9/99:35 amMDW - BOS
1 stop5h 12mDelta
Deal found 5/28$316
Wed 6/125:20 amBOS - MDW
1 stop4h 28mDelta
Wed 6/191:24 pmMDW - BOS
1 stop5h 25mDelta
Deal found 5/27$318
Tue 6/48:14 amBOS - MDW
1 stop6h 21mDelta
Tue 6/119:34 amMDW - BOS
1 stop5h 22mDelta
Deal found 5/27$319
Wed 6/265:20 amBOS - MDW
1 stop4h 28mDelta
Wed 7/35:45 pmMDW - BOS
1 stop5h 14mDelta
Deal found 5/28$320
Thu 7/115:20 amBOS - MDW
1 stop4h 18mDelta
Sat 7/135:45 pmMDW - BOS
1 stop5h 07mDelta
Deal found 5/27$321
Wed 6/265:20 amBOS - MDW
1 stop4h 28mDelta
Sat 6/295:45 pmMDW - BOS
1 stop5h 11mDelta
Deal found 5/26$325
Mon 6/36:05 amBOS - MDW
1 stop8h 30mDelta
Wed 6/59:46 amMDW - BOS
1 stop8h 24mDelta
Deal found 5/27$326
Thu 8/295:20 amBOS - MDW
1 stop4h 18mDelta
Fri 8/301:24 pmMDW - BOS
1 stop5h 26mDelta
Deal found 5/28$356

Cheap Boston to Midway flights in May & June 2024

Find cheap flight options from Boston to Midway specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,740,132 searches. Prices were last updated on May 28, 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.
Wed 6/57:49 amBOS - MDW
1 stop6h 43mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/27$126
Wed 6/57:49 amBOS - MDW
1 stop6h 43mFrontier
Sun 6/98:53 pmMDW - BOS
1 stop10h 23mFrontier
Deal found 5/27$146
Wed 6/127:49 amBOS - MDW
1 stop6h 43mFrontier
Tue 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/27$148
Thu 6/612:22 pmBOS - MDW
1 stop8h 34mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/27$156
Fri 6/79:16 amBOS - MDW
1 stop23h 39mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/27$158
Wed 6/197:49 amBOS - MDW
1 stop6h 43mFrontier
Tue 6/2510:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/27$160
Wed 6/267:49 amBOS - MDW
1 stop6h 43mFrontier
Tue 7/210:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/27$164
Fri 6/79:16 amBOS - MDW
1 stop23h 39mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/28$166
Wed 6/197:49 amBOS - MDW
1 stop6h 43mFrontier
Sun 6/238:53 pmMDW - BOS
1 stop10h 23mFrontier
Deal found 5/27$168

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 2,740,132 searches. Data last updated May 28, 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.
Wed 6/57:49 amBOS - MDW
1 stop6h 43mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/27$126
Wed 8/1412:36 pmBOS - MDW
1 stop7h 37mFrontier
Tue 8/207:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 5/27$136
Tue 8/2012:36 pmBOS - MDW
1 stop7h 37mFrontier
Tue 8/277:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 5/27$144
Wed 6/57:49 amBOS - MDW
1 stop6h 43mFrontier
Sun 6/98:53 pmMDW - BOS
1 stop10h 23mFrontier
Deal found 5/27$146
Wed 6/127:49 amBOS - MDW
1 stop6h 43mFrontier
Tue 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/27$148
Wed 8/1412:36 pmBOS - MDW
1 stop7h 37mFrontier
Sat 8/177:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 5/27$156
Fri 6/79:16 amBOS - MDW
1 stop23h 39mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/27$158
Tue 8/1312:36 pmBOS - MDW
1 stop7h 37mFrontier
Sat 8/177:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 5/27$159
Wed 6/197:49 amBOS - MDW
1 stop6h 43mFrontier
Tue 6/2510:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/27$160

Non-stop flights to Midway from Boston

Discover non-stop flight options from Boston to Midway. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,740,132 searches. Data last updated May 28, 2024.
To help reduce your travel time, choose from one of these non-stop flights from Boston to Chicago. If you're looking for other options for flights from Boston to Chicago, make sure to update the search form at the top of page.
Sun 6/166:30 amBOS - MDW
Nonstop2h 35mSouthwest
Sat 6/226:05 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 5/27$244

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 2,740,132 searches. Data last updated May 28, 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.
Wed 6/57:49 amBOS - MDW
1 stop6h 43mFrontier
Sun 6/98:53 pmMDW - BOS
1 stop10h 23mFrontier
Deal found 5/27$146
Thu 6/612:22 pmBOS - MDW
1 stop8h 34mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/27$156
Fri 6/79:16 amBOS - MDW
1 stop23h 39mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/27$158
Fri 6/79:16 amBOS - MDW
1 stop23h 39mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/28$166
Thu 6/612:22 pmBOS - MDW
1 stop8h 34mFrontier
Sun 6/98:53 pmMDW - BOS
1 stop10h 23mFrontier
Deal found 5/27$176
Thu 6/612:22 pmBOS - MDW
1 stop8h 34mFrontier
Sun 6/98:53 pmMDW - BOS
1 stop10h 23mFrontier
Deal found 5/27$186
Wed 6/57:49 amBOS - MDW
1 stop6h 43mFrontier
Sun 6/98:53 pmMDW - BOS
1 stop10h 23mFrontier
Deal found 5/27$187
Wed 6/57:49 amBOS - MDW
1 stop6h 43mFrontier
Fri 6/712:57 pmMDW - BOS
1 stop19h 50mFrontier
Deal found 5/27$191
Wed 6/57:49 amBOS - MDW
1 stop6h 43mFrontier
Sun 6/98:53 pmMDW - BOS
1 stop10h 23mFrontier
Deal found 5/27$217

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 2,740,132 searches. Data last updated May 28, 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.
Wed 6/57:49 amBOS - MDW
1 stop6h 43mFrontier
Deal found 5/27$58
Wed 6/57:49 amBOS - MDW
1 stop6h 43mFrontier
Deal found 5/26$62
Mon 6/107:49 amBOS - MDW
1 stop6h 49mFrontier
Deal found 5/28$66
Wed 6/127:49 amBOS - MDW
1 stop6h 43mFrontier
Deal found 5/27$68
Wed 8/289:16 amBOS - MDW
1 stop13h 39mFrontier
Deal found 5/28$69
Wed 6/127:49 amBOS - MDW
1 stop6h 43mFrontier
Deal found 5/28$72
Wed 6/127:49 amBOS - MDW
1 stop6h 43mFrontier
Deal found 5/28$73
Tue 6/1112:36 pmBOS - MDW
1 stop9h 44mFrontier
Deal found 5/28$74
Tue 8/2712:36 pmBOS - MDW
1 stop7h 37mFrontier
Deal found 5/27$76

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 2,740,132 searches. Data last updated May 28, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$136 - $374

Route

Depart

Return

Price

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 8/14

1 stop7h 37m

Chicago Midway

Tue 8/20

1 stop10h 26m

$136

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 8/20

1 stop7h 37m

Chicago Midway

Tue 8/27

1 stop10h 26m

$144

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 6/12

1 stop6h 43m

Chicago Midway

Tue 6/18

1 stop7h 42m

$148

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 8/14

1 stop7h 37m

Chicago Midway

Sat 8/17

1 stop10h 26m

$156

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 6/7

1 stop23h 39m

Chicago Midway

Tue 6/11

1 stop7h 42m

$158

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 6/13

Nonstop2h 35m

Chicago Midway

Fri 6/14

Nonstop2h 15m

$216

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Sun 6/16

Nonstop2h 35m

Chicago Midway

Sat 6/22

2 stops6h 30m

$232

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 6/15

1 stop4h 28m

Chicago Midway

Sat 6/15

1 stop5h 11m

$314

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 6/15

1 stop20h 22m

Chicago Midway

Fri 6/21

1 stop10h 15m

$374

Flights are sorted by cheapest first

Deals found on 5/27

When is the cheapest time 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 May 26, 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

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 May 28, 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.
Southwest
8.2
Very good
5,984 reviews
Check prices

Food

7.3

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Overall

8.2

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
5,984 reviews
Southwest
8.2
Very good
5,984 reviews
Check prices

Food

7.3

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Overall

8.2

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
10,476 reviews
Southwest
8.2
Very good
5,984 reviews
Check prices

Food

7.3

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Overall

8.2

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
1,003 reviews
Southwest
8.2
Very good
5,984 reviews
Check prices

Food

7.3

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Overall

8.2

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
395 reviews
Southwest
8.2
Very good
5,984 reviews
Check prices

Food

7.3

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Overall

8.2

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
6.3
Okay
4,016 reviews
Southwest
8.2
Very good
5,984 reviews
Check prices

Food

7.3

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Overall

8.2

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 $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 $136, but on average you can expect to pay $162.

  • 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 $244.

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

    Nonstop flights are available for this route on the following days: Saturday.

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

    Travelers can expect 4 flights from Boston to Chicago Midway Airport on average per day.
    Morning (6am - Noon) - 50% of flight departures
    Afternoon (Noon - 6pm) - 25% of flight departures
    Evening (6pm - Midnight) - 25% of flight departures

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

    Frontier can get you from Boston to Chicago Midway Airport in just under 7h 37m. Your travel time can differ by up to . Boston and Chicago Midway Airport are separated by a distance of 863 mi.

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

    According to our current data, Frontier ($136), offers the cheapest pricing from Boston to Chicago Midway Airport. You may be able to fly from Boston to Chicago Midway Airport for 61% 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 5/27.

  • 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.

  • When is the best time 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 $248). 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

Browse thousands of different options on Cheapflights for your next trip

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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
Worcester to O'Hare Intl flights
Boston to Rockford flights
Hyannis to O'Hare Intl flights
West Tisbury 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 2,740,132 searches. Data last updated May 28, 2024.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$89Average$301FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
FrontierCheapest$97Average$151FlexibilityNo cancel feeOn-time62%
Search Frontier flights
American AirlinesCheapest$126Average$252FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
DeltaCheapest$315Average$453FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
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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 May 28, 2024.
3%of flight departuresEarly morningMidnight to 6 am
56%of flight departuresMorning6 am to noon
27%of flight departuresAfternoonNoon to 6 pm
14%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 May 28, 2024.
Sunday3daily flights
Monday5daily flights
Tuesday4daily flights
Wednesday4daily flights
Thursday5daily flights
Friday5daily flights
Saturday2daily flights

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Fly with Cheapflights

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Can Cheapflights notify me if prices for flights from Boston to Midway become cheaper?

Yes, Cheapflights offers price alerts on Boston to Midway flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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