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Cheap flights from Boston (BOS) to Midway (MDW) from $49

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 5/22. 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
May 11 — May 181
From?
To?
Sat 5/11
Sat 5/18
1 adult, Economy
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The best prices from Boston Logan Intl to Chicago Midway are usually found in December or April, booked 15 days in advance, depart on a Tuesday or Wednesday 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 May 6, 2024.

Popular in

October

Cheapest in

December

Round-trip from

$223

One-way from

$49
High demand for flights, 19% 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 103%.

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 24 days before your planned departure. Booking around this time can save you about 33% 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 $327.

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 46% on flights from Boston to Chicago Midway Airport by exploring options for tickets in the morning.

Cheap Frontier flights from Boston to Midway

Explore cheap flight options specifically provided by Frontier 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 2,689,106 searches. Data last updated May 6, 2024.
Find some of the cheapest Frontier flights traveling from Boston to Chicago. Be sure to come back soon if the deals available don't appeal to you at this time.
Wed 5/2211:14 amBOS - MDW
1 stop11h 39mFrontier
Wed 5/297:49 amMDW - BOS
1 stop23h 51mFrontier
Deal found 5/5$98
Sat 6/810:12 amBOS - MDW
1 stop24h 19mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/5$99
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 5/5$100
Mon 5/1312:41 pmBOS - MDW
1 stop11h 49mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 5/5$101
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Fri 5/1712:04 pmMDW - BOS
1 stop21h 35mFrontier
Deal found 5/5$102
Mon 5/1312:41 pmBOS - MDW
1 stop11h 49mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 5/5$103
Wed 5/2211:14 amBOS - MDW
1 stop11h 39mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/5$104
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Fri 5/171:15 pmMDW - BOS
2 stops20h 24mFrontier
Deal found 5/5$107
Wed 5/228:19 amBOS - MDW
1 stop6h 50mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/5$108

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 2,689,106 searches. Data last updated May 6, 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.
Tue 6/48:14 amBOS - MDW
1 stop6h 21mDelta
Tue 6/111:24 pmMDW - BOS
1 stop5h 25mDelta
Deal found 5/5$316
Tue 6/48:14 amBOS - MDW
1 stop6h 21mDelta
Fri 6/76:49 pmMDW - BOS
1 stop5h 42mDelta
Deal found 5/5$317
Thu 6/131:07 pmBOS - MDW
1 stop4h 57mDelta
Mon 6/175:45 pmMDW - BOS
1 stop5h 11mDelta
Deal found 5/5$318
Tue 6/48:14 amBOS - MDW
1 stop6h 21mDelta
Mon 6/105:45 pmMDW - BOS
1 stop5h 11mDelta
Deal found 5/4$322
Thu 6/65:35 amBOS - MDW
1 stop4h 31mDelta
Mon 6/105:45 pmMDW - BOS
1 stop5h 11mDelta
Deal found 5/5$323
Tue 5/215:35 amBOS - MDW
1 stop4h 31mDelta
Wed 5/299:32 amMDW - BOS
1 stop7h 13mDelta
Deal found 5/5$328
Thu 8/295:30 amBOS - MDW
1 stop4h 14mDelta
Sat 9/710:11 amMDW - BOS
1 stop8h 44mDelta
Deal found 5/5$351
Sat 5/114:15 pmBOS - MDW
1 stop6h 46mDelta
Tue 5/141:21 pmMDW - BOS
1 stop5h 51mDelta
Deal found 5/5$353
Fri 6/145:20 amBOS - MDW
1 stop4h 28mDelta
Wed 6/195:45 pmMDW - BOS
1 stop5h 11mDelta
Deal found 5/5$360

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 2,689,106 searches. Prices were last updated on May 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.
Wed 5/2211:14 amBOS - MDW
1 stop11h 39mFrontier
Wed 5/297:49 amMDW - BOS
1 stop23h 51mFrontier
Deal found 5/5$98
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 5/6$99
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 5/5$100
Mon 5/1312:41 pmBOS - MDW
1 stop11h 49mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 5/5$101
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Fri 5/1712:04 pmMDW - BOS
1 stop21h 35mFrontier
Deal found 5/5$102
Mon 5/1312:41 pmBOS - MDW
1 stop11h 49mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 5/6$103
Wed 5/2211:14 amBOS - MDW
1 stop11h 39mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/5$104
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Fri 5/171:15 pmMDW - BOS
2 stops20h 24mFrontier
Deal found 5/5$107
Wed 5/228:19 amBOS - MDW
1 stop6h 50mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/5$108

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 2,689,106 searches. Data last updated May 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.
Wed 5/2211:14 amBOS - MDW
1 stop11h 39mFrontier
Wed 5/297:49 amMDW - BOS
1 stop23h 51mFrontier
Deal found 5/5$98
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 5/6$99
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 5/5$100
Mon 5/1312:41 pmBOS - MDW
1 stop11h 49mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 5/5$101
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Fri 5/1712:04 pmMDW - BOS
1 stop21h 35mFrontier
Deal found 5/5$102
Mon 5/1312:41 pmBOS - MDW
1 stop11h 49mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 5/6$103
Wed 5/2211:14 amBOS - MDW
1 stop11h 39mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/5$104
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Fri 5/171:15 pmMDW - BOS
2 stops20h 24mFrontier
Deal found 5/5$107
Wed 5/228:19 amBOS - MDW
1 stop6h 50mFrontier
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/5$108

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 2,689,106 searches. Data last updated May 6, 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 5/5$327

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 2,689,106 searches. Data last updated May 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.
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 5/6$99
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 5/5$100
Mon 5/1312:41 pmBOS - MDW
1 stop11h 49mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 5/5$101
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Fri 5/1712:04 pmMDW - BOS
1 stop21h 35mFrontier
Deal found 5/5$102
Mon 5/1312:41 pmBOS - MDW
1 stop11h 49mFrontier
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 5/5$103
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Fri 5/171:15 pmMDW - BOS
2 stops20h 24mFrontier
Deal found 5/5$107
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Wed 5/297:49 amMDW - BOS
1 stop23h 51mFrontier
Deal found 5/6$109
Mon 5/1312:41 pmBOS - MDW
1 stop11h 49mFrontier
Wed 5/297:49 amMDW - BOS
1 stop23h 51mFrontier
Deal found 5/6$111
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Sun 5/197:49 amMDW - BOS
1 stop24h 15mFrontier
Deal found 5/5$112

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 2,689,106 searches. Data last updated May 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.
Wed 5/228:19 amBOS - MDW
1 stop6h 50mFrontier
Deal found 5/5$49
Wed 5/298:19 amBOS - MDW
1 stop6h 50mFrontier
Deal found 5/4$50
Wed 6/57:49 amBOS - MDW
1 stop6h 43mFrontier
Deal found 5/5$54
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Deal found 5/5$56
Sat 5/189:49 amBOS - MDW
1 stop22h 05mFrontier
Deal found 5/5$60
Sat 6/112:59 pmBOS - MDW
1 stop7h 58mFrontier
Deal found 5/5$61
Mon 5/1312:41 pmBOS - MDW
1 stop11h 49mFrontier
Deal found 5/6$63
Tue 6/1112:36 pmBOS - MDW
1 stop9h 44mFrontier
Deal found 5/5$64
Sat 5/1811:29 amBOS - MDW
2 stops20h 25mFrontier
Deal found 5/5$65

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 2,689,106 searches. Data last updated May 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$98 - $327

Route

Depart

Return

Price

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 5/22

1 stop11h 39m

Chicago Midway

Wed 5/29

1 stop23h 51m

$98

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 6/8

1 stop24h 19m

Chicago Midway

Tue 6/11

1 stop7h 42m

$99

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 5/22

1 stop11h 39m

Chicago Midway

Tue 6/11

1 stop7h 42m

$104

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 5/22

1 stop6h 50m

Chicago Midway

Tue 6/11

1 stop7h 42m

$108

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 5/29

1 stop22h 02m

Chicago Midway

Mon 6/3

1 stop8h 27m

$116

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 6/3

1 stop11h 05m

Chicago Midway

Tue 6/11

1 stop7h 42m

$118

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 5/22

1 stop6h 50m

Chicago Midway

Mon 6/3

1 stop8h 27m

$121

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 6/4

1 stop6h 21m

Chicago Midway

Tue 6/11

1 stop5h 25m

$316

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

Sun 6/16

Nonstop2h 35m

Chicago Midway

Sat 6/22

Nonstop2h 15m

$327

Flights are sorted by cheapest first

Deals found on 5/5

When is the best time to 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 May 3, 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 15 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Search Deals

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 April 28, 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

Average price of flights to Midway by month

Plan your trip from Boston to Midway by taking into account the cheapest months to travel. The average price of a one-way flight from Boston to Midway is currently $58 while a round-trip flight costs $156. Price data was last updated on April 28, 2024.

Currently, December is the cheapest month in which you can book a flight from Boston to Chicago Midway Airport (average of $140). Flying from Boston to Chicago Midway Airport in July is currently the most expensive (average of $251). 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.

January

$194

February

$190

March

$219

April

$159

May

$185

June

$235

July

$251

August

$196

September

$157

October

$143

November

$165

December

$140

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 6, 2024.
Peruse reviews from past customers who have flown with Frontier, Delta and Southwest 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
6,084 reviews
Check prices

Overall

8.2

Boarding

8.3

Crew

8.7

Food

7.3

Entertainment

7.8

Comfort

8.1

Reviews

1 / 10

The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.

Southwest
8.2
Very good
6,084 reviews
Southwest
8.2
Very good
6,084 reviews
Check prices

Overall

8.2

Boarding

8.3

Crew

8.7

Food

7.3

Entertainment

7.8

Comfort

8.1

Reviews

1 / 10

The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.

Delta
8.1
Very good
10,818 reviews
Southwest
8.2
Very good
6,084 reviews
Check prices

Overall

8.2

Boarding

8.3

Crew

8.7

Food

7.3

Entertainment

7.8

Comfort

8.1

Reviews

1 / 10

The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.

Allegiant Air
7.5
Good
1,025 reviews
Southwest
8.2
Very good
6,084 reviews
Check prices

Overall

8.2

Boarding

8.3

Crew

8.7

Food

7.3

Entertainment

7.8

Comfort

8.1

Reviews

1 / 10

The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.

Porter Airlines
7.4
Good
430 reviews
Southwest
8.2
Very good
6,084 reviews
Check prices

Overall

8.2

Boarding

8.3

Crew

8.7

Food

7.3

Entertainment

7.8

Comfort

8.1

Reviews

1 / 10

The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.

Frontier
6.3
Okay
4,090 reviews
Southwest
8.2
Very good
6,084 reviews
Check prices

Overall

8.2

Boarding

8.3

Crew

8.7

Food

7.3

Entertainment

7.8

Comfort

8.1

Reviews

1 / 10

The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.

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 $98, but on average you can expect to pay $123.

  • Are there nonstop flights from Boston to Chicago Midway Airport for under $400 on Cheapflights?

    Cheapflights has at least 1 direct flight from Boston to Chicago Midway Airport under $400. A good price for a nonstop flight from Boston to Chicago Midway Airport is less than $327.

  • Are there last-minute flights available from Boston to Chicago Midway Airport for under $100?

    There are currently 20+ open flights from Boston to Chicago Midway Airport within the next 7 days for less than $100.

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

    According to our current data, Frontier ($98), offers the cheapest pricing from Boston to Chicago Midway Airport. You may be able to fly from Boston to Chicago Midway Airport for 71% less than the average price by searching for this airline.

  • 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 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 5/6.

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.

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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 2,689,106 searches. Data last updated May 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$89Average$326FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
FrontierCheapest$97Average$147FlexibilityNo cancel feeOn-time62%
Search Frontier flights
American AirlinesCheapest$126Average$252FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
DeltaCheapest$315Average$464FlexibilityNo 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.
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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 6, 2024.
1%of flight departuresEarly morningMidnight to 6 am
53%of flight departuresMorning6 am to noon
15%of flight departuresAfternoonNoon to 6 pm
31%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 6, 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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How does Cheapflights help users find flights from Boston to Midway?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Boston to Midway. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Boston to Midway?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Boston to Midway for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Boston to Midway with no change fees?

Certainly. Search results for flights to Midway from Boston shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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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