Cheap flights from Midway (MDW) to Boston (BOS) 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 8/13. 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.
MDW — BOS
jun. 25 — jul. 21

Cheap flight deals from Midway to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Boston (BOS). 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 20, 2024.

Popular in

October

Cheapest in

May

Round-trip from

$218

One-way from

$49
High demand for flights, 35% potential price rise
Best time to find cheap flights, 70% potential price drop
From Chicago Midway to Boston Logan Intl
One-way flight from Chicago Midway to Boston Logan Intl

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

Leaving on a Tuesday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 132% on the overall cost on flights from Chicago Midway Airport to Boston.

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

Users have found that booking a flight from Chicago Midway Airport to Boston at least 31 days early can save you up to 33% on average compared to booking a flight this week. If booking 31 days before your flight isn’t an option for you, users have found flights from Chicago Midway Airport to Boston for as little as $267 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $346 for flights departing within the next 3 days.

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

January is one of the best times of the year to fly to Boston from Chicago Midway Airport. Prices for January average $263 per person but you can even find prices for as low as $99. The most expensive prices can be found in the month of April. Opting for a January flight can save you 15% on your journey compared to booking in April

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

It’s optimal to fly from Chicago Midway Airport to Boston in the evening. By choosing this option you can save up to 62% on the cost of your flight, compared to a flight at noon.

Cheap Midway to Boston flights in June & July 2024

Find cheap flight options from Midway to Boston specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,256,981 searches. Prices were last updated on junio 20, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to Boston in 2024. Check back in a little while for more flight options.
jue. 7/48:51 pmMDW - BOS
1 stop10h 35mFrontier
vie. 9/2711:35 amBOS - MDW
1 stop12h 06mFrontier
Deal found 6/19$133
mié. 7/102:29 pmMDW - BOS
1 stop8h 58mFrontier
mar. 7/1610:58 amBOS - MDW
1 stop11h 27mFrontier
Deal found 6/19$143
jue. 7/259:04 pmMDW - BOS
1 stop10h 22mFrontier
lun. 7/296:00 amBOS - MDW
1 stop8h 28mFrontier
Deal found 6/19$149
vie. 7/122:23 pmMDW - BOS
1 stop9h 04mFrontier
mar. 7/1610:58 amBOS - MDW
1 stop11h 27mFrontier
Deal found 6/20$152
mié. 7/102:29 pmMDW - BOS
1 stop8h 58mFrontier
lun. 7/156:00 amBOS - MDW
1 stop8h 28mFrontier
Deal found 6/20$155
vie. 7/192:23 pmMDW - BOS
1 stop9h 04mFrontier
mié. 7/246:00 amBOS - MDW
1 stop8h 34mFrontier
Deal found 6/20$156
vie. 7/122:23 pmMDW - BOS
1 stop9h 04mFrontier
mar. 7/1610:58 amBOS - MDW
1 stop11h 27mFrontier
Deal found 6/19$159
jue. 7/48:51 pmMDW - BOS
1 stop10h 35mFrontier
lun. 7/86:00 amBOS - MDW
1 stop8h 28mFrontier
Deal found 6/18$160
vie. 7/126:11 pmMDW - BOS
1 stop14h 17mFrontier
lun. 7/156:00 amBOS - MDW
1 stop8h 28mFrontier
Deal found 6/19$162

Midway to Boston 2024 flight deals

Discover exclusive flight deals for travel between Midway and Boston in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,256,981 searches. Data last updated junio 20, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to Boston in 2024. Check back in a little while for more flight options.
mar. 8/274:24 pmMDW - BOS
1 stop7h 07mFrontier
mar. 9/106:00 amBOS - MDW
1 stop5h 55mFrontier
Deal found 6/20$97
mar. 8/277:59 pmMDW - BOS
1 stop10h 26mFrontier
sáb. 9/712:50 pmBOS - MDW
1 stop9h 23mFrontier
Deal found 6/20$100
jue. 9/197:59 pmMDW - BOS
1 stop10h 26mFrontier
mié. 9/259:16 amBOS - MDW
1 stop13h 39mFrontier
Deal found 6/19$102
mié. 8/287:59 pmMDW - BOS
1 stop10h 26mFrontier
lun. 9/912:20 pmBOS - MDW
1 stop7h 53mFrontier
Deal found 6/20$103
sáb. 8/317:59 pmMDW - BOS
1 stop10h 26mFrontier
mié. 9/411:35 amBOS - MDW
1 stop12h 06mFrontier
Deal found 6/19$104
jue. 8/297:59 pmMDW - BOS
1 stop10h 26mFrontier
vie. 9/612:36 pmBOS - MDW
1 stop7h 37mFrontier
Deal found 6/20$106
mar. 8/134:24 pmMDW - BOS
1 stop7h 07mFrontier
jue. 8/156:00 amBOS - MDW
1 stop8h 55mFrontier
Deal found 6/19$107
mar. 8/134:24 pmMDW - BOS
1 stop7h 07mFrontier
mar. 8/2012:36 pmBOS - MDW
1 stop7h 37mFrontier
Deal found 6/20$108
vie. 9/207:59 pmMDW - BOS
1 stop9h 56mFrontier
dom. 9/2212:36 pmBOS - MDW
1 stop7h 37mFrontier
Deal found 6/20$109

Midway to Boston flights leaving soon

Find last-minute flight options from Midway to Boston 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 3,256,981 searches. Data last updated junio 20, 2024.
Check out these flights departing soon from Chicago to Boston. Users should be sure to double check the price, date, and time of their last-minute flight.
jue. 6/278:51 pmMDW - BOS
1 stop10h 25mFrontier
mar. 7/910:58 amBOS - MDW
1 stop11h 27mFrontier
Deal found 6/19$160
jue. 6/278:51 pmMDW - BOS
1 stop10h 25mFrontier
lun. 7/17:49 amBOS - MDW
1 stop6h 49mFrontier
Deal found 6/19$170
jue. 6/278:51 pmMDW - BOS
1 stop10h 25mFrontier
mar. 7/910:58 amBOS - MDW
1 stop11h 27mFrontier
Deal found 6/20$229
jue. 6/278:51 pmMDW - BOS
1 stop10h 25mFrontier
lun. 7/17:49 amBOS - MDW
1 stop6h 49mFrontier
Deal found 6/19$232
mar. 6/2510:16 pmMDW - BOS
1 stop7h 42mFrontier
vie. 6/289:29 amBOS - MDW
1 stop14h 29mFrontier
Deal found 6/19$247
vie. 6/281:11 pmMDW - BOS
1 stop18h 58mFrontier
sáb. 7/610:13 amBOS - MDW
1 stop24h 07mFrontier
Deal found 6/18$249
mar. 6/2510:16 pmMDW - BOS
1 stop7h 42mFrontier
vie. 6/289:29 amBOS - MDW
1 stop14h 29mFrontier
Deal found 6/20$251
mar. 6/256:15 pmMDW - BOS
Nonstop2h 15mSouthwest
mié. 6/263:00 pmBOS - MDW
Nonstop2h 40mSouthwest
Deal found 6/19$287
mar. 6/253:35 pmMDW - BOS
1 stop6h 40mSouthwest
mié. 6/263:00 pmBOS - MDW
Nonstop2h 40mSouthwest
Deal found 6/19$296

One-way flights to Boston from Midway

Search for one-way flight options from Midway to Boston. 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 3,256,981 searches. Data last updated junio 20, 2024.
Take a look at some of the one-way flights we've detected from Chicago to Boston. For those needing a return trip from Chicago, there is a search form available above.
mar. 8/134:24 pmMDW - BOS
1 stop7h 07mFrontier
Deal found 6/20$49
mar. 8/134:24 pmMDW - BOS
1 stop7h 07mFrontier
Deal found 6/18$50
mar. 8/204:24 pmMDW - BOS
1 stop7h 07mFrontier
Deal found 6/20$52
mié. 8/147:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/19$56
jue. 8/157:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/18$57
mar. 8/274:24 pmMDW - BOS
1 stop7h 07mFrontier
Deal found 6/18$58
vie. 8/238:54 pmMDW - BOS
1 stop14h 06mFrontier
Deal found 6/19$59
mié. 8/287:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/19$61
jue. 9/197:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/19$67

Find flights from Midway to Boston within your budget

Customize your flight search to find flights from Midway to Boston 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 3,256,981 searches. Data last updated junio 20, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$97 - $316

Route

Depart

Return

Price

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

mar. 8/27

1 stop7h 07m

Boston Logan Intl

mar. 9/10

1 stop5h 55m

$97

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

mar. 8/27

1 stop10h 26m

Boston Logan Intl

sáb. 9/7

1 stop9h 23m

$100

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

jue. 9/19

1 stop10h 26m

Boston Logan Intl

mié. 9/25

1 stop13h 39m

$102

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

vie. 8/23

1 stop9h 56m

Boston Logan Intl

mié. 8/28

1 stop12h 06m

$103

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

sáb. 8/31

1 stop10h 26m

Boston Logan Intl

mié. 9/4

1 stop12h 06m

$104

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

jue. 9/19

1 stop10h 26m

Boston Logan Intl

lun. 9/23

1 stop7h 53m

$106

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

mar. 8/13

1 stop7h 07m

Boston Logan Intl

jue. 8/15

1 stop8h 55m

$107

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

vie. 10/11

1 stop12h 12m

Boston Logan Intl

lun. 10/14

1 stop5h 23m

$313

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

mar. 7/9

1 stop5h 25m

Boston Logan Intl

mié. 7/17

1 stop4h 18m

$316

Flights are sorted by cheapest first

Deals found on 6/20

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

Use this chart to determine the cheapest time to fly round-trip from Midway to Boston. Price data was last updated on June 16, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago Midway Airport to Boston flight should consider departing on Wednesday mornings when fares are most often at their lowest. Sunday mornings 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 Midway to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Midway 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 Boston by month

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

BOS

Temperature

30.2 - 73.4 °F

If weather is an important factor for your trip to Boston, 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 30.2 F).

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated junio 20, 2024.
See what other customers who have flown with Frontier, Delta and Porter Airlines from Chicago to Boston have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

8.0
Very good
10,000 reviews
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

7.7
Good
440 reviews
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

7.5
Good
372 reviews
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

7.5
Good
981 reviews
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

6.2
Okay
3,932 reviews
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Crew

8.6

Boarding

8.2

Entertainment

8.0

Food

7.4

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Midway to Boston. 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 into for flights to Boston from Chicago Midway?

    Most people fly into Boston Logan Intl (BOS) if they book a flight to Boston from Chicago Midway. On average, Logan Intl has 3 inbound flights from Chicago Midway per day from 3 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

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

    Yes, there are multiple flights from Chicago Midway Airport to Boston for under $100. The cheapest flight booked recently is on Frontier for just $97, but on average you can expect to pay $114.

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

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

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

    Currently priced at $97, Frontier will fly you from Chicago Midway Airport to Boston and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Frontier is 70% cheaper than the average price of flights available within the next 90 days to this destination.

  • What does MDW to BOS mean?

    Chicago Midway Airport is MDW and Boston Logan Intl Airport is BOS. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service.

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

    The amount of baggage you can bring on your Midway to Boston 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 Midway to Boston with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Boston 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 Midway to Boston that include hotel bookings?

    Yes. In addition to deals on Midway to Boston flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Boston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Boston.

  • Can I find deals for business class flights from Midway to Boston?

    Yes. Cheapflights offers flight deals from Midway to Boston 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 Midway to Boston that allow pets onboard?

    Many airlines flying from Midway to Boston 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 Midway to Boston?

    Yes, you can often find last-minute deals on Midway to Boston 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 Chicago Midway Airport to Boston flight deals updated?

    The Chicago Midway Airport to Boston flight deals you see on this page were last updated on 6/20.

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Boston (average of $218). Flying from Chicago Midway Airport to Boston in July is currently the most expensive (average of $328). 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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Top 3 airlines flying from Midway to Boston

Discover the top 3 airlines that operate flights from Midway to Boston. 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 3,256,981 searches. Data last updated junio 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$63Average$409FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$84Average$322FlexibilityNo cancel feeOn-time69%
FrontierCheapest$84Average$168FlexibilityNo cancel feeOn-time62%

Search flights from Midway to Boston by cabin class

Find flights from Midway to Boston, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Hourly flight availability from Midway to Boston

Find hourly flight availability from Midway to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated junio 20, 2024.
13%of flight departuresEarly morningMidnight to 6 am
31%of flight departuresMorning6 am to noon
31%of flight departuresAfternoonNoon to 6 pm
25%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Midway to Boston

Explore weekly flight availability from Midway to Boston. 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 20, 2024.
Sunday3daily flights
Monday4daily flights
Tuesday4daily flights
Wednesday4daily flights
Thursday4daily flights
Friday4daily flights
Saturday2daily flights
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