$104+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Sep 27 — Oct 41
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Boston to Midway with Cheapflights
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.Cheapflights Tip: The best prices from Boston Logan Intl to Chicago Midway are usually found in December or January, booked 31 days in advance, depart on a Thursday or Friday and return on a Friday
Cheap flight deals from Boston to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Boston to MidwayExplore the most affordable flight options available from Boston to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 28, 2026.
Explore the most affordable flight options available from Boston to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 28, 2026.
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:45 pm -
Nonstop2h 45m
Mon 9/216:30 pm -
Nonstop2h 25m
Deal found 8/27![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:50 am -
Nonstop2h 35m
Thu 10/225:30 am -
Nonstop2h 25m
Deal found 8/27![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:10 pm -
Nonstop2h 35m
Sat 10/32:40 pm -
1 stop6h 25m
Deal found 8/27![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/14:50 pm -
Nonstop2h 40m
Mon 10/52:50 pm -
2 stops5h 30m
Deal found 8/27![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 8/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:40 pm -
Nonstop2h 45m
Mon 9/287:55 pm -
1 stop11h 05m
Deal found 8/25![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 8/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:40 pm -
Nonstop2h 45m
Fri 10/26:45 pm -
Nonstop2h 15m
Deal found 8/26![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 8/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:10 am -
1 stop8h 25m
Mon 11/96:10 pm -
1 stop4h 40m
Deal found 8/26![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:00 am -
2 stops9h 20m
Mon 9/215:45 am -
Nonstop2h 15m
Deal found 8/27![Southwest logo]()
$241
Best flights from Boston to MidwayDiscover carefully curated flight deals from Boston to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 28, 2026.
Discover carefully curated flight deals from Boston to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 28, 2026.
This Southwest deal was found by Cheapflights users on 8/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:45 pm -
Nonstop2h 45m
Mon 9/216:30 pm -
Nonstop2h 25m
Deal found 8/25![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:20 pm -
Nonstop2h 40m
Tue 9/222:00 pm -
1 stop7h 20m
Deal found 8/27![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:20 pm -
Nonstop2h 40m
Fri 10/26:45 pm -
Nonstop2h 15m
Deal found 8/27![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 8/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:50 am -
Nonstop2h 35m
Sun 10/115:00 am -
Nonstop2h 25m
Deal found 8/24![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 8/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:45 am -
1 stop8h 00m
Thu 10/295:30 am -
Nonstop2h 25m
Deal found 8/24![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 8/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:30 pm -
1 stop7h 55m
Mon 9/287:55 pm -
1 stop11h 05m
Deal found 8/26![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 8/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:40 pm -
Nonstop2h 45m
Fri 9/186:30 pm -
Nonstop2h 25m
Deal found 8/25![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 8/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2410:25 pm -
Nonstop2h 55m
Fri 11/2712:50 pm -
2 stops8h 40m
Deal found 8/23![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/227:30 pm -
1 stop5h 35m
Fri 11/276:45 pm -
Nonstop2h 15m
Deal found 8/27![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 8/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/135:30 am -
1 stop5h 25m
Mon 9/147:55 pm -
1 stop11h 05m
Deal found 8/26![Southwest logo]()
$300
Last-minute flights from Boston to MidwayDiscover last-minute flight deals from Boston to Midway. Data last updated August 28, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Midway. Data last updated August 28, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:40 am -
Nonstop2h 35m
Sat 9/193:10 pm -
Nonstop2h 25m
Deal found 8/26![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 8/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/154:55 pm -
1 stop4h 55m
Wed 9/166:40 am -
Nonstop2h 15m
Deal found 8/25![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:45 pm -
Nonstop2h 45m
Mon 9/216:30 pm -
Nonstop2h 25m
Deal found 8/27![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 8/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:45 pm -
Nonstop2h 45m
Wed 9/2312:45 pm -
1 stop4h 50m
Deal found 8/25![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:00 am -
2 stops9h 20m
Mon 9/215:45 am -
Nonstop2h 15m
Deal found 8/27![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:30 am -
Nonstop2h 35m
Wed 9/302:45 pm -
1 stop6h 30m
Deal found 8/27![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:20 pm -
1 stop6h 25m
Mon 9/289:20 am -
1 stop6h 45m
Deal found 8/27![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 8/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:40 pm -
Nonstop2h 45m
Mon 9/287:55 pm -
1 stop11h 05m
Deal found 8/25![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:40 pm -
Nonstop2h 45m
Mon 9/286:30 am -
Nonstop2h 15m
Deal found 8/27![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 8/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:40 pm -
Nonstop2h 45m
Fri 10/26:45 pm -
Nonstop2h 15m
Deal found 8/26![Southwest logo]()
$235
One-way flights from Boston to MidwaySearch for one-way flight options from Boston to Midway. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
Search for one-way flight options from Boston to Midway. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
This Frontier deal was found by Cheapflights users on 8/23. 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.
Fri 10/3012:39 pm -
1 stop12h 08m
Deal found 8/23![Frontier logo]()
$104
This Super.com deal was found by Cheapflights users on 8/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:54 pm -
1 stop5h 57m
Deal found 8/24![Frontier logo]()
$106
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:40 am -
Nonstop2h 35m
Deal found 8/27![Southwest logo]()
$109
This Super.com deal was found by Cheapflights users on 8/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2112:54 pm -
1 stop5h 57m
Deal found 8/27![Frontier logo]()
$110
This Super.com deal was found by Cheapflights users on 8/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:54 pm -
1 stop11h 50m
Deal found 8/25![Frontier logo]()
$112
This Frontier deal was found by Cheapflights users on 8/23. 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.
Sun 9/612:45 pm -
1 stop11h 02m
Deal found 8/23![Frontier logo]()
$114
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:45 pm -
Nonstop2h 45m
Deal found 8/27![Southwest logo]()
$118
This Southwest deal was found by Cheapflights users on 8/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/224:55 pm -
1 stop4h 55m
Deal found 8/26![Southwest logo]()
$119
Find 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 August 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $217 (Southwest) |
One-way from | $104 (Frontier) |
Popular in | November |
Cheapest in | December |
Average price | $312 |
Good round-trip deal | $282 or less |
Good one-way deal | $182 or less |
Cheapflights Fare Finder
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 7,457,451 searches. Data last updated August 28, 2026.
Use the filters below to find and compare flights from Boston to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Thu 9/17
6:45 pm-8:30 pm
Nonstop2h 45m
Chicago Midway
Mon 9/21
6:30 pm-9:55 pm
Nonstop2h 25m
$217
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Mon 9/21
8:20 pm-10:00 pm
Nonstop2h 40m
Chicago Midway
Tue 9/22
2:00 pm-10:20 pm
1 stop7h 20m
$227
Quickest round-trip
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Fri 9/25
8:20 pm-10:00 pm
Nonstop2h 40m
Chicago Midway
Fri 10/2
6:45 pm-10:00 pm
Nonstop2h 15m
$235
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Thu 10/8
5:50 am-7:25 am
Nonstop2h 35m
Chicago Midway
Sun 10/11
5:00 am-8:25 am
Nonstop2h 25m
$236
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sat 10/24
10:45 am-5:45 pm
1 stop8h 00m
Chicago Midway
Thu 10/29
5:30 am-8:55 am
Nonstop2h 25m
$236
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Fri 9/25
4:30 pm-11:25 pm
1 stop7h 55m
Chicago Midway
Mon 9/28
7:55 pm-8:00 am
1 stop11h 05m
$251
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Mon 9/14
6:40 pm-8:25 pm
Nonstop2h 45m
Chicago Midway
Fri 9/18
6:30 pm-9:55 pm
Nonstop2h 25m
$285
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Tue 11/24
10:25 pm-12:20 am
Nonstop2h 55m
Chicago Midway
Fri 11/27
12:50 pm-10:30 pm
2 stops8h 40m
$290
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sun 11/22
7:30 pm-12:05 am
1 stop5h 35m
Chicago Midway
Fri 11/27
6:45 pm-10:00 pm
Nonstop2h 15m
$295
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sun 9/13
5:30 am-9:55 am
1 stop5h 25m
Chicago Midway
Mon 9/14
7:55 pm-8:00 am
1 stop11h 05m
$300
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from Boston to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Midway in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Boston-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Boston-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
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.
BOS-MDW
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.
Cheapflights Insights
Everything you need to know about your flight from Boston to Chicago Midway Airport
How far ahead should I book a flight from Boston to Chicago Midway Airport?
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 30 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Boston to Chicago Midway Airport?
Currently, December is the cheapest month in which you can book a flight from Boston to Chicago Midway Airport (average of $137). Flying from Boston to Chicago Midway Airport in November is currently the most expensive (average of $400). 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.
What is the cheapest time of day to fly from BOS to MDW?
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 August 28, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 22% on flights from Boston to Chicago Midway Airport by exploring options for tickets in the evening.
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 August 22, 2026.
Travelers seeking maximum savings on their Boston to Chicago Midway Airport flight should consider departing on Friday evenings 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.
The best insider tips for Boston to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Boston to Chicago Midway Airport trip
Our travel experts
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 August 28, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andAmerican Airlines from Boston to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Find flights from Boston to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 28, 2026.
Boston and Midway flights
Browse other Boston and Midway flight options. Last updated on August 28, 2026.
Other flights from Boston
Browse through other flights departing from Boston. Flights are based on user searches made on Cheapflights and were last updated on August 28, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated August 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$385 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$213 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$295 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$181 | Average$227 | FlexibilityNo cancel fee | On-time71% |