$102+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Sep 12 — Sep 191
Round-trip
1 adult, Economy
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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 13, 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 13, 2026.
This Southwest deal was found by Cheapflights users on 8/12. 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 9/106:40 pm -
Nonstop2h 45m
Tue 9/156:40 am -
Nonstop2h 15m
Deal found 8/12![Southwest logo]()
$165
This Southwest deal was found by Cheapflights users on 8/10. 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 9/38:20 pm -
Nonstop2h 45m
Mon 9/75:45 am -
Nonstop2h 15m
Deal found 8/10![Southwest logo]()
$166
This Southwest deal was found by Cheapflights users on 8/11. 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 10/249:40 am -
Nonstop2h 35m
Mon 10/262:50 pm -
2 stops5h 30m
Deal found 8/11![Southwest logo]()
$176
This Southwest deal was found by Cheapflights users on 8/11. 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 9/178:20 pm -
Nonstop2h 40m
Mon 9/217:55 pm -
1 stop11h 05m
Deal found 8/11![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 8/12. 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 10/2610:00 pm -
Nonstop2h 35m
Fri 10/305:30 am -
Nonstop2h 25m
Deal found 8/12![Southwest logo]()
$184
This Delta deal was found by Cheapflights users on 8/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:55 am -
1 stop8h 25m
Sat 10/39:59 am -
1 stop8h 16m
Deal found 8/11![Delta logo]()
$185
This Southwest deal was found by Cheapflights users on 8/12. 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 10/245:15 am -
2 stops13h 45m
Thu 10/295:30 am -
Nonstop2h 25m
Deal found 8/12![Southwest logo]()
$186
This Southwest deal was found by Cheapflights users on 8/10. 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 10/235:50 am -
Nonstop2h 35m
Mon 10/265:30 am -
Nonstop2h 25m
Deal found 8/10![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 8/10. 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 9/46:40 pm -
Nonstop2h 45m
Thu 9/105:45 am -
Nonstop2h 15m
Deal found 8/10![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 8/12. 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 9/91:20 pm -
1 stop6h 25m
Wed 9/162:00 pm -
2 stops7h 15m
Deal found 8/12![Southwest logo]()
$190
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 13, 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 13, 2026.
This Southwest deal was found by Cheapflights users on 8/12. 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 9/107:40 am -
2 stops8h 15m
Mon 9/147:55 pm -
1 stop11h 05m
Deal found 8/12![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/205:40 am -
1 stop4h 27m
Wed 9/231:00 pm -
1 stop7h 12m
Deal found 8/12![Delta logo]()
$250
This Southwest deal was found by Cheapflights users on 8/10. 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 10/177:40 am -
Nonstop2h 35m
Wed 10/211:10 pm -
Nonstop2h 20m
Deal found 8/10![Southwest logo]()
$196
This Southwest deal was found by Cheapflights users on 8/10. 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
Thu 9/175:45 am -
Nonstop2h 15m
Deal found 8/10![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 8/10. 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 9/232:40 pm -
1 stop6h 35m
Deal found 8/10![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 8/8. 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 9/125:30 am -
1 stop5h 00m
Sun 9/136:00 am -
Nonstop2h 15m
Deal found 8/8![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 8/11. 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 8/278:20 pm -
Nonstop2h 40m
Sun 8/306:00 am -
Nonstop2h 15m
Deal found 8/11![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 8/12. 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
Sat 9/197:40 am -
2 stops7h 10m
Deal found 8/12![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 8/10. 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 8/316:40 pm -
Nonstop2h 40m
Fri 9/45:45 am -
Nonstop2h 15m
Deal found 8/10![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 8/8. 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 9/67:55 am -
1 stop10h 30m
Mon 9/75:45 am -
Nonstop2h 15m
Deal found 8/8![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/9. 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 11/101:20 pm -
1 stop6h 35m
Thu 11/125:05 am -
2 stops8h 25m
Deal found 8/9![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 8/12. 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 8/268:15 am -
2 stops5h 50m
Sat 8/297:40 am -
Nonstop2h 20m
Deal found 8/12![Southwest logo]()
$270
Last-minute flights from Boston to MidwayDiscover last-minute flight deals from Boston to Midway. Data last updated August 13, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Midway. Data last updated August 13, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/10. 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 9/38:20 pm -
Nonstop2h 45m
Mon 9/75:45 am -
Nonstop2h 15m
Deal found 8/10![Southwest logo]()
$166
This Southwest deal was found by Cheapflights users on 8/10. 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 9/46:40 pm -
Nonstop2h 45m
Thu 9/105:45 am -
Nonstop2h 15m
Deal found 8/10![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 8/10. 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 9/55:00 am -
2 stops9h 20m
Mon 9/75:45 am -
Nonstop2h 15m
Deal found 8/10![Southwest logo]()
$193
This Southwest deal was found by Cheapflights users on 8/12. 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 9/95:45 pm -
1 stop5h 10m
Wed 9/162:00 pm -
2 stops7h 15m
Deal found 8/12![Southwest logo]()
$190
This Southwest deal was found by Cheapflights users on 8/12. 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 9/106:40 pm -
Nonstop2h 45m
Mon 9/145:45 am -
Nonstop2h 15m
Deal found 8/12![Southwest logo]()
$165
This Southwest deal was found by Cheapflights users on 8/12. 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 9/125:30 am -
2 stops8h 00m
Wed 9/162:00 pm -
2 stops7h 15m
Deal found 8/12![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 8/11. 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 9/178:20 pm -
Nonstop2h 40m
Mon 9/217:55 pm -
1 stop11h 05m
Deal found 8/11![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 8/11. 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
Mon 9/215:45 am -
Nonstop2h 15m
Deal found 8/11![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 8/9. 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 9/195:30 am -
1 stop5h 00m
Tue 9/222:00 pm -
2 stops7h 15m
Deal found 8/9![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:55 am -
1 stop8h 25m
Sat 10/39:59 am -
1 stop8h 16m
Deal found 8/12![Delta logo]()
$185
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 13, 2026.
Search for one-way flight options from Boston to Midway. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
This Super.com deal was found by Cheapflights users on 8/11. 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.
Sun 8/3012:45 pm -
1 stop11h 02m
Deal found 8/11![Frontier logo]()
$102
This Priceline deal was found by Cheapflights users on 8/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:35 pm -
1 stop10h 18m
Deal found 8/10![Frontier logo]()
$104
This Southwest deal was found by Cheapflights users on 8/11. 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 9/46:40 pm -
Nonstop2h 45m
Deal found 8/11![Southwest logo]()
$105
This Southwest deal was found by Cheapflights users on 8/12. 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 10/39:05 am -
2 stops9h 55m
Deal found 8/12![Southwest logo]()
$110
This Southwest deal was found by Cheapflights users on 8/12. 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 9/55:00 am -
2 stops9h 20m
Deal found 8/12![Southwest logo]()
$111
This Southwest deal was found by Cheapflights users on 8/9. 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 9/198:40 am -
Nonstop2h 35m
Deal found 8/9![Southwest logo]()
$114
This Super.com deal was found by Cheapflights users on 8/10. 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.
Wed 8/1912:45 pm -
1 stop11h 02m
Deal found 8/10![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 8/12. 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 8/2012:45 pm -
1 stop11h 02m
Deal found 8/12![Frontier logo]()
$118
This iWofly deal was found by Cheapflights users on 8/11. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:45 pm -
1 stop11h 02m
Deal found 8/11![Frontier 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 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $165 (Southwest) |
One-way from | $102 (Super.com) |
Popular in | November |
Cheapest in | December |
Average price | $311 |
Good round-trip deal | $262 or less |
Good one-way deal | $185 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 2,558,603 searches. Data last updated August 13, 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 9/10
7:40 am-2:55 pm
2 stops8h 15m
Chicago Midway
Mon 9/14
7:55 pm-8:00 am
1 stop11h 05m
$196
Quickest round-trip
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sat 10/17
7:40 am-9:15 am
Nonstop2h 35m
Chicago Midway
Wed 10/21
1:10 pm-4:30 pm
Nonstop2h 20m
$196
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
Thu 9/17
5:45 am-9:00 am
Nonstop2h 15m
$210
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Wed 9/23
7:30 am-9:05 am
Nonstop2h 35m
Chicago Midway
Wed 9/23
2:40 pm-10:15 pm
1 stop6h 35m
$220
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sun 9/20
5:40 am-9:07 am
1 stop4h 27m
Chicago Midway
Wed 9/23
1:00 pm-9:12 pm
1 stop7h 12m
$250
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sat 9/12
5:30 am-9:30 am
1 stop5h 00m
Chicago Midway
Sun 9/13
6:00 am-9:15 am
Nonstop2h 15m
$251
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Thu 8/27
8:20 pm-10:00 pm
Nonstop2h 40m
Chicago Midway
Sun 8/30
6:00 am-9:15 am
Nonstop2h 15m
$255
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Fri 9/18
6:45 pm-8:30 pm
Nonstop2h 45m
Chicago Midway
Sat 9/19
7:40 am-3:50 pm
2 stops7h 10m
$256
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Mon 8/31
6:40 pm-8:20 pm
Nonstop2h 40m
Chicago Midway
Fri 9/4
5:45 am-9:00 am
Nonstop2h 15m
$261
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sun 9/6
7:55 am-5:25 pm
1 stop10h 30m
Chicago Midway
Mon 9/7
5:45 am-9:00 am
Nonstop2h 15m
$266
Showing 1-10 of 24 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 $357). 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 13, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 25% 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 8, 2026.
Travelers seeking maximum savings on their Boston to Chicago Midway Airport flight should consider departing on Thursday 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 13, 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.
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
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?
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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 2,558,603 searches. Data last updated August 13, 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$135 | Average$291 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$181 | Average$227 | FlexibilityNo cancel fee | On-time71% |