$112+ Cheap flights from Boston (BOS) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Nov 20 — Nov 271
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 35 days in advance, depart on a Thursday or Friday and return on a Tuesday
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 October 21, 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 October 21, 2026.
This Trip.com deal was found by Cheapflights users on 10/20. 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.
Mon 11/1612:39 pm -
1 stop12h 08m
Thu 11/196:42 pm -
1 stop11h 59m
Deal found 10/20![Frontier logo]()
$212
This Southwest deal was found by Cheapflights users on 10/21. 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 12/35:55 pm -
Nonstop2h 45m
Sun 12/61:00 pm -
Nonstop2h 10m
Deal found 10/21![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 10/19. 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 12/312:50 pm -
Nonstop2h 50m
Thu 12/101:15 pm -
Nonstop2h 05m
Deal found 10/19![Southwest logo]()
$214
This Frontier deal was found by Cheapflights users on 10/19. 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.
Thu 11/1912:39 pm -
1 stop12h 08m
Sun 11/228:42 pm -
1 stop12h 29m
Deal found 10/19![Frontier logo]()
$215
This Frontier deal was found by Cheapflights users on 10/16. 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.
Sat 11/1411:27 am -
1 stop7h 20m
Tue 11/248:42 pm -
1 stop12h 29m
Deal found 10/16![Frontier logo]()
$220
This CheapOair deal was found by Cheapflights users on 10/19. 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.
Wed 11/1812:39 pm -
1 stop12h 08m
Sun 11/228:42 pm -
1 stop12h 29m
Deal found 10/19![Frontier logo]()
$225
This Frontier deal was found by Cheapflights users on 10/20. 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 12/1810:28 am -
1 stop10h 02m
Sun 12/208:35 pm -
1 stop11h 58m
Deal found 10/20![Frontier logo]()
$227
This Southwest deal was found by Cheapflights users on 10/19. 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 12/312:50 pm -
Nonstop2h 50m
Mon 12/71:15 pm -
2 stops7h 40m
Deal found 10/19![Southwest logo]()
$229
This Frontier deal was found by Cheapflights users on 10/16. 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.
Sat 11/1411:27 am -
1 stop7h 20m
Sun 11/228:42 pm -
1 stop12h 29m
Deal found 10/16![Frontier logo]()
$230
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 October 21, 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 October 21, 2026.
This Delta deal was found by Cheapflights users on 10/19. 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.
Tue 11/109:15 am -
1 stop4h 36m
Sat 11/146:44 pm -
1 stop4h 10m
Deal found 10/19![Delta logo]()
$233
This Southwest deal was found by Cheapflights users on 10/19. 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 1/135:20 pm -
1 stop5h 00m
Wed 1/278:15 am -
2 stops6h 50m
Deal found 10/19![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 10/19. 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 1/81:10 pm -
Nonstop2h 45m
Mon 1/1110:55 am -
2 stops6h 30m
Deal found 10/19![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 10/19. 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 12/31:20 pm -
2 stops7h 25m
Fri 12/41:15 pm -
2 stops7h 40m
Deal found 10/19![Southwest logo]()
$274
This Southwest deal was found by Cheapflights users on 10/19. 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 11/127:05 am -
Nonstop2h 45m
Mon 11/166:25 pm -
Nonstop2h 20m
Deal found 10/19![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 10/20. 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 12/67:25 am -
1 stop7h 15m
Sun 12/68:25 pm -
1 stop10h 55m
Deal found 10/20![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 10/17. 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 11/157:05 am -
Nonstop2h 45m
Sun 11/228:25 pm -
1 stop10h 40m
Deal found 10/17![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 10/16. 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 11/191:20 pm -
2 stops7h 25m
Sun 11/227:50 am -
2 stops6h 50m
Deal found 10/16![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 10/16. 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 11/54:20 pm -
Nonstop2h 45m
Sat 11/77:40 am -
Nonstop2h 15m
Deal found 10/16![Southwest logo]()
$335
This Southwest deal was found by Cheapflights users on 10/17. 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 12/2411:20 am -
2 stops9h 25m
Fri 1/18:30 am -
Nonstop2h 30m
Deal found 10/17![Southwest logo]()
$350
This Southwest deal was found by Cheapflights users on 10/16. 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 11/45:55 pm -
Nonstop2h 45m
Thu 11/55:05 am -
2 stops8h 25m
Deal found 10/16![Southwest logo]()
$350
This Southwest deal was found by Cheapflights users on 10/17. 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 11/1312:45 pm -
Nonstop2h 45m
Sun 11/158:25 pm -
1 stop10h 55m
Deal found 10/17![Southwest logo]()
$351
Last-minute flights from Boston to MidwayDiscover last-minute flight deals from Boston to Midway. Data last updated October 21, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Midway. Data last updated October 21, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/19. 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 11/97:05 am -
Nonstop2h 45m
Tue 11/101:15 pm -
Nonstop2h 05m
Deal found 10/19![Southwest logo]()
$214
This Southwest deal was found by Cheapflights users on 10/20. 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 11/105:55 pm -
Nonstop2h 45m
Wed 11/118:30 am -
Nonstop2h 30m
Deal found 10/20![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 10/20. 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 11/122:30 pm -
1 stop8h 30m
Wed 11/186:25 pm -
Nonstop2h 20m
Deal found 10/20![Southwest logo]()
$223
This Frontier deal was found by Cheapflights users on 10/21. 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.
Thu 11/1212:39 pm -
1 stop12h 08m
Thu 11/196:42 pm -
1 stop11h 59m
Deal found 10/21![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 10/16. 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.
Sat 11/1411:27 am -
1 stop7h 20m
Tue 11/248:42 pm -
1 stop12h 29m
Deal found 10/16![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 10/16. 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.
Sat 11/1411:27 am -
1 stop7h 20m
Sun 11/228:42 pm -
1 stop12h 29m
Deal found 10/16![Frontier logo]()
$230
This Trip.com deal was found by Cheapflights users on 10/20. 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.
Mon 11/1612:39 pm -
1 stop12h 08m
Thu 11/196:42 pm -
1 stop11h 59m
Deal found 10/20![Frontier logo]()
$212
This CheapOair deal was found by Cheapflights users on 10/19. 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.
Wed 11/1812:39 pm -
1 stop12h 08m
Sun 11/228:42 pm -
1 stop12h 29m
Deal found 10/19![Frontier logo]()
$225
This Frontier deal was found by Cheapflights users on 10/19. 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.
Thu 11/1912:39 pm -
1 stop12h 08m
Sun 11/228:42 pm -
1 stop12h 29m
Deal found 10/19![Frontier logo]()
$215
This Southwest deal was found by Cheapflights users on 10/21. 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 11/235:10 am -
1 stop10h 00m
Thu 11/267:45 am -
Nonstop2h 20m
Deal found 10/21![Southwest logo]()
$229
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 October 21, 2026.
Search for one-way flight options from Boston to Midway. Find affordable one-way fares based on user searches. Data last updated October 21, 2026.
This Trip.com deal was found by Cheapflights users on 10/17. 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.
Tue 11/1712:15 pm -
1 stop6h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$112
This Super.com deal was found by Cheapflights users on 10/16. 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 11/1112:39 pm -
1 stop12h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 10/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1311:08 am -
1 stop9h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$115
This Frontier deal was found by Cheapflights users on 10/18. 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.
Wed 11/1812:39 pm -
1 stop12h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$116
This Delta deal was found by Cheapflights users on 10/19. 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 11/219:15 am -
1 stop4h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$117
This Super.com deal was found by Cheapflights users on 10/21. 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.
Sat 11/711:27 am -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$118
This Expedia deal was found by Cheapflights users on 10/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/312:15 pm -
1 stop6h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$120
This Southwest deal was found by Cheapflights users on 10/20. 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 12/81:20 pm -
2 stops7h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Southwest logo]()
$122
This Super.com deal was found by Cheapflights users on 10/20. 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 11/412:39 pm -
1 stop12h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$124
This CheapOair deal was found by Cheapflights users on 10/20. 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.
Thu 12/1011:08 am -
1 stop9h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$125
This Super.com deal was found by Cheapflights users on 10/16. 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 11/2011:06 am -
1 stop9h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$126
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 October 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $212 (Trip.com) |
One-way from | $112 (Trip.com) |
Popular in | October |
Cheapest in | December |
Average price | $371 |
Good round-trip deal | $326 or less |
Good one-way deal | $181 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 October 21, 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
Sat 11/21
9:15 am-12:51 pm
1 stop4h 36m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Thu 12/31
5:35 pm-9:30 pm
1 stop4h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Tue 12/1
5:20 am-12:05 pm
1 stop7h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Tue 1/5
1:20 pm-7:45 pm
2 stops7h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$122
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Fri 11/13
4:20 pm-6:05 pm
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$137
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sat 11/21
6:55 pm-8:40 pm
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$144
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Fri 11/6
6:30 pm-8:15 pm
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$168
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Thu 11/5
7:05 am-8:50 am
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$168
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Mon 12/28
10:25 pm-12:25 am
Nonstop3h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$168
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Tue 11/10
5:55 pm-7:40 pm
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$168
Showing 1-10 of 23 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 October.
| 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 |
- 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 34 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 $134). Flying from Boston to Chicago Midway Airport in October is currently the most expensive (average of $371). 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 October 21, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 14% on flights from Boston to Chicago Midway Airport by exploring options for tickets at noon.
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 October 17, 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. Tuesday evenings 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
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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 October 21, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andJetBlue 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.
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.4
Overall
7.9
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Midway
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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 7,457,451 searches. Data last updated October 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$385 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$147 | Average$311 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$150 | Average$261 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$181 | Average$295 | FlexibilityNo cancel fee | On-time71% |