HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

$50+ Cheap flights from Boston (BOS) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
lip 31 — sie 71
From?
To?
śr. 7/31
śr. 8/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Leverage Cheapflights for Your Next Trip

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 Lipiec 26, 2024.

Popular in

June

Cheapest in

December

Round-trip from

$103
(mytrip.com)

One-way from

$50
(Gotogate)
High demand for flights, 22% potential price rise
Search Deals
Best time to find cheap flights, 42% potential price drop
Search Deals
From Boston Logan Intl to Chicago Midway
Search Deals
One-way flight from Boston Logan Intl to Chicago Midway
Search Deals

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 184%.

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 40% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $238 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 April. 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 50% on flights from Boston to Chicago Midway Airport by exploring options for tickets in the morning.

Cheap Boston to Midway flights in July & August 2024

Find cheap flight options from Boston to Midway specifically for the months of July and August 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Prices were last updated on Lipiec 26, 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.
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
śr. 8/2811:08 amBOS - MDW
1 stop5h 43mFrontier
śr. 9/44:46 pmMDW - BOS
1 stop6h 41mFrontier
Deal found 7/25$103
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sob. 8/1712:50 pmBOS - MDW
1 stop11h 59mFrontier
sob. 8/245:16 pmMDW - BOS
1 stop6h 11mFrontier
Deal found 7/25$106
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sob. 8/176:00 amBOS - MDW
1 stop9h 02mFrontier
wt. 8/202:30 pmMDW - BOS
1 stop9h 01mFrontier
Deal found 7/25$107
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
śr. 8/2811:08 amBOS - MDW
1 stop5h 43mFrontier
czw. 9/56:53 pmMDW - BOS
1 stop4h 30mFrontier
Deal found 7/25$108
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sob. 8/246:00 amBOS - MDW
1 stop9h 02mFrontier
czw. 8/295:25 pmMDW - BOS
1 stop6h 02mFrontier
Deal found 7/25$111
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sob. 8/1712:50 pmBOS - MDW
1 stop11h 59mFrontier
pon. 8/192:01 pmMDW - BOS
1 stop17h 10mFrontier
Deal found 7/25$112
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ndz. 8/2512:56 pmBOS - MDW
1 stop25h 10mFrontier
śr. 8/2811:05 amMDW - BOS
1 stop12h 26mFrontier
Deal found 7/24$114
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
czw. 8/2210:58 amBOS - MDW
1 stop10h 11mFrontier
czw. 8/295:25 pmMDW - BOS
1 stop6h 02mFrontier
Deal found 7/25$115
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sob. 8/1712:50 pmBOS - MDW
1 stop11h 59mFrontier
pt. 8/232:13 pmMDW - BOS
1 stop9h 14mFrontier
Deal found 7/25$116

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 2,752,877 searches. Data last updated Lipiec 26, 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.
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
śr. 8/2811:08 amBOS - MDW
1 stop5h 43mFrontier
śr. 9/44:46 pmMDW - BOS
1 stop6h 41mFrontier
Deal found 7/25$103
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wt. 9/106:00 amBOS - MDW
1 stop5h 19mFrontier
wt. 9/172:30 pmMDW - BOS
1 stop9h 00mFrontier
Deal found 7/24$104
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
śr. 9/256:00 amBOS - MDW
1 stop4h 50mFrontier
sob. 9/282:53 pmMDW - BOS
1 stop8h 30mFrontier
Deal found 7/25$106
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sob. 8/176:00 amBOS - MDW
1 stop9h 02mFrontier
wt. 8/202:30 pmMDW - BOS
1 stop9h 01mFrontier
Deal found 7/25$107
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
śr. 8/2811:08 amBOS - MDW
1 stop5h 43mFrontier
czw. 9/56:53 pmMDW - BOS
1 stop4h 30mFrontier
Deal found 7/25$108
This FlightNetwork deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightNetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sob. 9/711:33 amBOS - MDW
1 stop13h 10mFrontier
pon. 9/92:07 pmMDW - BOS
1 stop9h 16mFrontier
Deal found 7/25$110
This Frontier deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
śr. 10/26:00 amBOS - MDW
1 stop4h 50mFrontier
pon. 10/72:07 pmMDW - BOS
1 stop9h 16mFrontier
Deal found 7/24$111
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sob. 8/1712:50 pmBOS - MDW
1 stop11h 59mFrontier
pon. 8/192:01 pmMDW - BOS
1 stop17h 10mFrontier
Deal found 7/25$112
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
śr. 9/256:00 amBOS - MDW
1 stop4h 50mFrontier
pt. 9/276:59 pmMDW - BOS
1 stop4h 24mFrontier
Deal found 7/25$113

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 2,752,877 searches. Data last updated Lipiec 26, 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.
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
czw. 8/110:58 amBOS - MDW
1 stop10h 11mFrontier
śr. 8/72:29 pmMDW - BOS
1 stop8h 58mFrontier
Deal found 7/24$200
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wt. 7/3010:58 amBOS - MDW
1 stop11h 27mFrontier
pt. 8/302:13 pmMDW - BOS
1 stop9h 14mFrontier
Deal found 7/25$214
This CheapOair deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
czw. 8/110:58 amBOS - MDW
1 stop10h 11mFrontier
pt. 8/26:11 pmMDW - BOS
1 stop14h 12mFrontier
Deal found 7/25$217
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wt. 7/3010:58 amBOS - MDW
1 stop11h 27mFrontier
sob. 8/315:16 pmMDW - BOS
1 stop6h 11mFrontier
Deal found 7/25$225
This CheapOair deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pt. 8/29:41 amBOS - MDW
1 stop14h 17mFrontier
ndz. 8/49:04 pmMDW - BOS
1 stop10h 22mFrontier
Deal found 7/24$227
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wt. 7/3010:58 amBOS - MDW
1 stop11h 27mFrontier
pt. 8/26:11 pmMDW - BOS
1 stop14h 12mFrontier
Deal found 7/24$239
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
czw. 8/110:58 amBOS - MDW
1 stop10h 11mFrontier
śr. 8/72:29 pmMDW - BOS
1 stop8h 58mFrontier
Deal found 7/25$248
This Trip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
śr. 7/319:26 amBOS - MDW
1 stop14h 33mFrontier
śr. 8/72:29 pmMDW - BOS
1 stop8h 58mFrontier
Deal found 7/24$258
This CheapOair deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sob. 8/310:23 amBOS - MDW
1 stop24h 22mFrontier
sob. 8/315:16 pmMDW - BOS
1 stop6h 11mFrontier
Deal found 7/25$268

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 2,752,877 searches. Data last updated Lipiec 26, 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.
This Gotogate deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
śr. 9/186:00 amBOS - MDW
1 stop4h 50mFrontier
Deal found 7/24$50
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wt. 10/296:00 amBOS - MDW
1 stop5h 55mFrontier
Deal found 7/24$51
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wt. 9/246:00 amBOS - MDW
1 stop5h 19mFrontier
Deal found 7/24$52
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
śr. 8/2111:08 amBOS - MDW
1 stop5h 43mFrontier
Deal found 7/24$53
This Frontier deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wt. 10/16:00 amBOS - MDW
1 stop5h 19mFrontier
Deal found 7/24$54
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pon. 10/286:00 amBOS - MDW
1 stop5h 55mFrontier
Deal found 7/24$56
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sob. 9/2811:33 amBOS - MDW
1 stop13h 10mFrontier
Deal found 7/24$57
This Frontier deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
czw. 9/56:00 amBOS - MDW
1 stop5h 42mFrontier
Deal found 7/24$58
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sob. 8/1712:50 pmBOS - MDW
1 stop11h 59mFrontier
Deal found 7/24$59

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 2,752,877 searches. Data last updated Lipiec 26, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$103 - $316

Route

Depart

Return

Price

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

śr. 8/28

1 stop5h 43m

Chicago Midway

śr. 9/4

1 stop6h 41m

$103

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

wt. 9/10

1 stop5h 19m

Chicago Midway

wt. 9/17

1 stop9h 00m

$104

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

śr. 9/25

1 stop4h 50m

Chicago Midway

sob. 9/28

1 stop8h 30m

$106

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

sob. 8/17

1 stop9h 02m

Chicago Midway

wt. 8/20

1 stop9h 01m

$107

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

śr. 8/28

1 stop5h 43m

Chicago Midway

czw. 9/5

1 stop4h 30m

$108

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

sob. 9/7

1 stop13h 10m

Chicago Midway

pon. 9/9

1 stop9h 16m

$110

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

sob. 9/7

Nonstop2h 40m

Chicago Midway

ndz. 9/8

Nonstop2h 15m

$265

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

pt. 9/13

1 stop6h 49m

Chicago Midway

ndz. 9/15

3 stops37h 18m

$311

Boston Logan IntlChicago Midway

BOS - MDW

BOSMDW

Boston Logan Intl

ndz. 8/11

1 stop4h 18m

Chicago Midway

śr. 8/14

1 stop5h 22m

$316

Flights are sorted by cheapest first

Deals found on 7/25

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 July 21, 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 Lipiec 26, 2024.
Peruse reviews from past customers who have flown with Frontier, Porter Airlines and Delta 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
5,641 reviews

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Food

7.3

Overall

8.2

Crew

8.7

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
5,641 reviews
Southwest
8.2
Very good
5,641 reviews

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Food

7.3

Overall

8.2

Crew

8.7

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
9,630 reviews
Southwest
8.2
Very good
5,641 reviews

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Food

7.3

Overall

8.2

Crew

8.7

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
7.6
Good
344 reviews
Southwest
8.2
Very good
5,641 reviews

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Food

7.3

Overall

8.2

Crew

8.7

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
938 reviews
Southwest
8.2
Very good
5,641 reviews

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Food

7.3

Overall

8.2

Crew

8.7

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
3,835 reviews
Southwest
8.2
Very good
5,641 reviews

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Food

7.3

Overall

8.2

Crew

8.7

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 $103, but on average you can expect to pay $114.

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

    Cheapflights has at least 3 direct flights from Boston to Chicago Midway Airport under $300. A good price for a nonstop flight from Boston to Chicago Midway Airport is less than $256.

  • 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 ($103), offers the cheapest pricing from Boston to Chicago Midway Airport. You may be able to fly from Boston to Chicago Midway Airport for 70% 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 7/25.

  • 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, September is the cheapest month in which you can book a flight from Boston to Chicago Midway Airport (average of $137). Flying from Boston to Chicago Midway Airport in July is currently the most expensive (average of $231). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Hyannis to O'Hare Intl flights
West Tisbury to O'Hare Intl flights
Worcester to O'Hare Intl flights
Nantucket to O'Hare Intl flights
New Bedford to O'Hare Intl flights
Hartford to Rockford flights
Provincetown 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 2,752,877 searches. Data last updated Lipiec 26, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$153FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$126Average$252FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$180Average$326FlexibilityNo cancel feeOn-time69%
DeltaCheapest$316Average$446FlexibilityNo cancel feeOn-timeN/A
Baltimore to Tampa flights
Tampa to Seattle flights
Honolulu to Kaua'i flights
San Diego to Boston flights
Denver to Seattle flights
Miami to Los Angeles flights
San Francisco to Mexico City flights
USA to Hyderabad flights
Los Angeles to Honolulu flights
Boston to Dublin flights
USA to Dhaka flights
Boston to Mendoza flights

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 Lipiec 26, 2024.
1%of flight departuresEarly morningMidnight to 6 am
33%of flight departuresMorning6 am to noon
50%of flight departuresAfternoonNoon to 6 pm
16%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 Lipiec 26, 2024.
Sunday3daily flights
Monday5daily flights
Tuesday4daily flights
Wednesday4daily flights
Thursday5daily flights
Friday5daily flights
Saturday2daily flights

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Flights to Abha
Flights to Komatsu
Flights to Skardu
Flights to Laayoune Hassan I
Flights to Aqaba King Hussein Intl
Flights to Nampula
Flights to Bourgas
Flights to Riverton
Flights to Alpena Phelps/Collins
Flights to Palmas
Flights to Newport State
Flights to Antofagasta Cerro Moreno
Flights to Nuku‘alofa Fua'Amotu Intl
Flights to Ndola
Flights to Fort Dodge
Flights to Miri
Flights to Rhinelander Oneida County
Flights to Seattle Lake Union Spb
Flights to Portsmouth Pease Intl
Flights to Tumbes
Flights to Jigiga
Flights to Diyarbakir
Flights to Akureyri
Flights to Brainerd Crow Wing County
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines