$111+ Cheap flights from Midway (MDW) to Boston (BOS)
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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Nov 13 — Nov 201
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Midway to Boston 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 Chicago Midway to Boston Logan Intl are usually found in February or November, booked 42 days in advance, depart on a Friday or Tuesday and return on a Thursday
Cheap flight deals from Midway to Boston
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to BostonExplore the most affordable flight options available from Midway to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2026.
Explore the most affordable flight options available from Midway to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2026.
This Southwest deal was found by Cheapflights users on 10/13. 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 11/49:55 am -
1 stop6h 15m
Mon 11/97:30 pm -
1 stop5h 40m
Deal found 10/13![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 10/13. 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 11/48:30 am -
Nonstop2h 30m
Sat 11/78:10 am -
2 stops10h 15m
Deal found 10/13![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 10/13. 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 11/109:55 am -
2 stops8h 10m
Mon 11/161:20 pm -
1 stop6h 35m
Deal found 10/13![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 10/13. 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 11/136:45 pm -
Nonstop2h 20m
Mon 11/167:10 am -
Nonstop2h 45m
Deal found 10/13![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 10/13. 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 11/111:15 pm -
2 stops7h 40m
Mon 11/1611:20 am -
2 stops9h 25m
Deal found 10/13![Southwest logo]()
$231
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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.
Thu 11/196:42 pm -
1 stop11h 59m
Sun 11/2211:06 am -
1 stop9h 41m
Deal found 10/14![Frontier logo]()
$233
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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.
Fri 11/208:42 pm -
1 stop12h 29m
Sun 11/2211:06 am -
1 stop9h 41m
Deal found 10/14![Frontier logo]()
$234
This Frontier deal was found by Cheapflights users on 10/14. 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 12/139:37 pm -
1 stop11h 36m
Fri 1/810:24 am -
1 stop10h 18m
Deal found 10/14![Frontier logo]()
$235
This Cheapflightsfares deal was found by Cheapflights users on 10/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/208:07 pm -
1 stop13h 55m
Mon 1/1110:24 am -
1 stop10h 18m
Deal found 10/10![Frontier logo]()
$236
This Frontier deal was found by Cheapflights users on 10/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/219:23 pm -
1 stop10h 17m
Mon 1/1110:24 am -
1 stop10h 18m
Deal found 10/11![Frontier logo]()
$238
Best flights from Midway to BostonDiscover carefully curated flight deals from Midway to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 14, 2026.
Discover carefully curated flight deals from Midway to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 14, 2026.
This Southwest deal was found by Cheapflights users on 10/13. 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 11/43:50 pm -
1 stop4h 55m
Wed 11/181:20 pm -
2 stops7h 25m
Deal found 10/13![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 10/14. 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 11/66:10 pm -
1 stop4h 45m
Mon 11/96:30 pm -
Nonstop2h 45m
Deal found 10/14![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 10/13. 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 11/96:45 pm -
Nonstop2h 20m
Tue 11/105:55 pm -
Nonstop2h 45m
Deal found 10/13![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 10/12. 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 11/304:20 pm -
2 stops7h 20m
Sat 12/57:15 am -
Nonstop2h 45m
Deal found 10/12![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 10/12. 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 11/136:30 pm -
2 stops12h 40m
Sun 11/157:05 am -
Nonstop2h 45m
Deal found 10/12![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 10/11. 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 11/51:00 pm -
Nonstop2h 10m
Mon 11/97:05 am -
Nonstop2h 45m
Deal found 10/11![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 10/9. 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 11/77:40 am -
Nonstop2h 15m
Mon 11/94:20 pm -
Nonstop2h 45m
Deal found 10/9![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 10/10. 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 12/116:45 pm -
Nonstop2h 15m
Wed 12/1612:50 pm -
Nonstop2h 50m
Deal found 10/10![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 10/9. 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 12/195:50 pm -
1 stop4h 50m
Tue 12/2210:25 pm -
Nonstop2h 55m
Deal found 10/9![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 10/13. 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 10/305:30 am -
Nonstop2h 25m
Mon 11/212:45 pm -
Nonstop2h 45m
Deal found 10/13![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 10/12. 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 11/198:10 am -
2 stops6h 40m
Sun 11/227:05 am -
Nonstop2h 45m
Deal found 10/12![Southwest logo]()
$329
Last-minute flights from Midway to BostonDiscover last-minute flight deals from Midway to Boston. Data last updated October 14, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Boston. Data last updated October 14, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/13. 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 11/49:55 am -
1 stop6h 15m
Mon 11/97:30 pm -
1 stop5h 40m
Deal found 10/13![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 10/13. 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 11/48:30 am -
Nonstop2h 30m
Sat 11/78:10 am -
2 stops10h 15m
Deal found 10/13![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 10/12. 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 11/77:40 am -
Nonstop2h 15m
Mon 11/96:30 pm -
Nonstop2h 45m
Deal found 10/12![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 10/13. 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 11/106:00 am -
1 stop5h 20m
Tue 11/171:20 pm -
2 stops7h 25m
Deal found 10/13![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 10/13. 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 11/111:15 pm -
2 stops7h 40m
Mon 11/1611:20 am -
2 stops9h 25m
Deal found 10/13![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 10/13. 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 11/136:45 pm -
Nonstop2h 20m
Mon 11/167:10 am -
Nonstop2h 45m
Deal found 10/13![Southwest logo]()
$229
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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.
Thu 11/196:42 pm -
1 stop11h 59m
Sun 11/2211:06 am -
1 stop9h 41m
Deal found 10/14![Frontier logo]()
$233
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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.
Fri 11/208:42 pm -
1 stop12h 29m
Sun 11/2211:06 am -
1 stop9h 41m
Deal found 10/14![Frontier logo]()
$234
One-way flights from Midway to BostonSearch for one-way flight options from Midway to Boston. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
Search for one-way flight options from Midway to Boston. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
This Southwest deal was found by Cheapflights users on 10/13. 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 11/412:50 pm -
1 stop5h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Southwest logo]()
$111
This Southwest deal was found by Cheapflights users on 10/13. 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 11/98:15 pm -
1 stop11h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Southwest logo]()
$116
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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.
Fri 12/49:43 pm -
1 stop11h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$121
This Cheapflightsfares deal was found by Cheapflights users on 10/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:42 pm -
1 stop12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 10/13. 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 12/39:43 pm -
1 stop11h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$123
This Frontier deal was found by Cheapflights users on 10/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/139:37 pm -
1 stop11h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$124
This CheapOair deal was found by Cheapflights users on 10/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:42 pm -
1 stop11h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$126
This Southwest deal was found by Cheapflights users on 10/13. 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 12/116:45 pm -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Southwest logo]()
$129
This Cheapflightsfares deal was found by Cheapflights users on 10/13. 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.
Fri 12/119:37 pm -
1 stop11h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:26 pm -
1 stop16h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Allegiant Air logo]()
$133
This Frontier deal was found by Cheapflights users on 10/14. 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.
Mon 1/118:47 pm -
1 stop11h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$134
Find flight deals from Midway to Boston
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Boston (BOS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $221 (Southwest) |
One-way from | $111 (Southwest) |
Popular in | September |
Cheapest in | February |
Average price | $418 |
Good round-trip deal | $335 or less |
Good one-way deal | $147 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Boston that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 14, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Boston that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sat 12/5
7:40 am-10:55 am
Nonstop2h 15m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Wed 11/18
8:30 am-12:00 pm
Nonstop2h 30m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 12/21
7:45 am-11:00 am
Nonstop2h 15m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 1/7
9:00 am-12:15 pm
Nonstop2h 15m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
Quickest round-trip
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sun 12/13
1:00 pm-4:10 pm
Nonstop2h 10m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 10/29
11:00 am-2:25 pm
Nonstop2h 25m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sat 12/12
10:24 am-6:35 pm
1 stop7h 11m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 11/26
8:40 am-5:20 pm
2 stops7h 40m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sat 11/7
8:00 am-5:30 pm
2 stops8h 30m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Tue 12/8
6:00 am-2:58 pm
1 stop7h 58m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$167
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from Midway to Boston
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 Midway to Boston 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 Chicago Midway Airport-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Boston flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Boston 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 Chicago Midway Airport-Boston 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 Midway to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston from Midway with our price prediction graph.
MDW-BOS
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 Chicago Midway Airport to Boston
Prices
Delays
How far ahead should I book a flight from Chicago Midway Airport to Boston?
To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Boston, you should look to book at least 41 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Chicago Midway Airport to Boston?
Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Boston (average of $277). Flying from Chicago Midway Airport to Boston in September is currently the most expensive (average of $427). 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 MDW to BOS?
Find hourly flight availability from Midway to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 14, 2026.
It’s optimal to fly from Chicago Midway Airport to Boston in the evening. By choosing this option you can save up to 13% on the cost of your flight, compared to a flight in the morning.
What is the cheapest day to fly from Chicago Midway Airport to Boston?
Use this chart to determine the cheapest time to fly round-trip from Midway to Boston. Price data was last updated on October 10, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Boston flight should consider departing on Tuesday at noon 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.
How often are flights from Chicago to Boston delayed?
About 27% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 137 minutes.
What is the most punctual flight time for Chicago to Boston flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Boston flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 27% of flights being delayed.
The best insider tips for Chicago Midway Airport to Boston 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 Chicago Midway Airport to Boston trip
Our travel experts
Reviews of airlines servicing Boston
Get insights into the airlines that provide service to Boston. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Boston. Reviews last updated October 14, 2026.
Get a feel of what it's like to fly with Southwest from Chicago Midway Airport to Boston by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Related info for your journey
Find useful and relevant information for your journey from Midway to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWaltham
Randolph
Concord
Cambridge
Brockton
Dedham
Cranston
Warwick
Pawtucket
Peabody
Londonderry
York Beach
Revere
Fitchburg
North Falmouth
Chelsea
Swansea
Braintree
Auburn
Sandwich
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
Boston flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Midway
Popular flights
Alternative routes for Midway to Boston
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Boston
Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 14, 2026.
Complete your trip
Complete your trip to Boston by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Boston by cabin class
Find flights from Midway to Boston, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Boston flights
Browse other Midway and Boston flight options. Last updated on October 14, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on October 14, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Midway to Boston
Discover the top airline that operate flights from Midway to Boston. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$157 | Average$332 | FlexibilityNo cancel fee | On-time63% |