$93+ Cheap flights from Midway (MDW) to Boston (BOS)
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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Sep 10 — Sep 171
Round-trip
1 adult, Economy
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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 September or December, booked 35 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 August 11, 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 August 11, 2026.
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 9/105:45 am -
Nonstop2h 15m
Mon 9/146:40 pm -
Nonstop2h 45m
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.
Wed 11/113:50 pm -
1 stop4h 50m
Mon 11/165:55 pm -
Nonstop2h 45m
Deal found 8/10![Southwest logo]()
$175
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 9/911:55 am -
2 stops5h 40m
Wed 9/167:15 pm -
Nonstop2h 40m
Deal found 8/10![Southwest logo]()
$180
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 9/115:45 am -
Nonstop2h 15m
Mon 9/148:20 pm -
Nonstop2h 40m
Deal found 8/10![Southwest logo]()
$184
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 10/172:40 pm -
1 stop6h 25m
Tue 10/205:35 am -
1 stop6h 45m
Deal found 8/10![Southwest logo]()
$185
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 9/84:40 pm -
1 stop4h 40m
Sat 9/127:05 am -
Nonstop2h 35m
Deal found 8/9![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.
Fri 10/25:30 am -
Nonstop2h 25m
Tue 10/610:55 am -
Nonstop2h 35m
Deal found 8/9![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 10/34:25 pm -
Nonstop2h 20m
Tue 10/610:55 am -
Nonstop2h 35m
Deal found 8/10![Southwest logo]()
$196
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 August 11, 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 August 11, 2026.
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 9/193:10 pm -
Nonstop2h 25m
Tue 9/222:45 pm -
1 stop7h 05m
Deal found 8/10![Southwest logo]()
$206
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 10/149:10 am -
Nonstop2h 20m
Sat 10/177:40 am -
Nonstop2h 35m
Deal found 8/10![Southwest logo]()
$227
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.
Mon 9/75:45 am -
Nonstop2h 15m
Mon 9/148:20 pm -
Nonstop2h 40m
Deal found 8/8![Southwest logo]()
$255
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 9/238:40 am -
2 stops6h 20m
Sat 9/265:50 am -
2 stops8h 15m
Deal found 8/10![Southwest logo]()
$257
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 8/275:45 am -
Nonstop2h 15m
Sat 8/294:35 pm -
1 stop4h 55m
Deal found 8/10![Southwest logo]()
$265
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.
Fri 10/3012:45 pm -
Nonstop2h 20m
Mon 11/24:20 pm -
Nonstop2h 45m
Deal found 8/8![Southwest logo]()
$270
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.
Sun 10/185:00 am -
Nonstop2h 25m
Sun 10/2510:50 pm -
Nonstop2h 35m
Deal found 8/9![Southwest logo]()
$275
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.
Thu 8/279:00 am -
1 stop4h 30m
Sun 9/67:55 am -
1 stop10h 30m
Deal found 8/8![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/294:20 pm -
2 stops6h 45m
Mon 11/27:30 pm -
1 stop5h 35m
Deal found 8/7![Southwest logo]()
$280
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 8/1912:50 pm -
Nonstop2h 20m
Mon 8/243:55 pm -
Nonstop2h 35m
Deal found 8/10![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 8/6. 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 9/147:55 pm -
1 stop11h 05m
Thu 9/172:15 pm -
1 stop5h 00m
Deal found 8/6![Southwest logo]()
$286
Last-minute flights from Midway to BostonDiscover last-minute flight deals from Midway to Boston. Data last updated August 11, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Boston. Data last updated August 11, 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.
Mon 8/315:45 am -
Nonstop2h 15m
Tue 9/295:25 am -
1 stop7h 10m
Deal found 8/10![Southwest logo]()
$175
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 9/84:40 pm -
1 stop4h 40m
Sat 9/127:05 am -
Nonstop2h 35m
Deal found 8/9![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.
Tue 9/84:40 pm -
1 stop4h 40m
Tue 9/157:15 pm -
Nonstop2h 40m
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.
Wed 9/911:55 am -
2 stops5h 40m
Wed 9/167:15 pm -
Nonstop2h 40m
Deal found 8/10![Southwest logo]()
$180
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 9/105:45 am -
Nonstop2h 15m
Mon 9/146:40 pm -
Nonstop2h 45m
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 9/115:45 am -
Nonstop2h 15m
Mon 9/148:20 pm -
Nonstop2h 40m
Deal found 8/10![Southwest logo]()
$184
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 9/151:00 pm -
2 stops8h 15m
Sat 9/195:30 am -
1 stop5h 00m
Deal found 8/9![Southwest logo]()
$191
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.
Tue 9/226:40 am -
Nonstop2h 15m
Mon 10/2610:00 pm -
Nonstop2h 35m
Deal found 8/10![Southwest logo]()
$196
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 August 11, 2026.
Search for one-way flight options from Midway to Boston. Find affordable one-way fares based on user searches. Data last updated August 11, 2026.
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 8/3110:30 am -
1 stop6h 20m
Deal found 8/10![Southwest logo]()
$93
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 9/217:55 pm -
1 stop11h 05m
Deal found 8/10![Southwest logo]()
$98
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 9/116:30 pm -
Nonstop2h 25m
Deal found 8/10![Southwest logo]()
$101
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:00 pm -
Nonstop2h 25m
Deal found 8/6![Southwest logo]()
$104
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 9/84:40 pm -
1 stop4h 40m
Deal found 8/9![Southwest logo]()
$105
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.
Tue 9/226:40 am -
Nonstop2h 15m
Deal found 8/10![Southwest logo]()
$114
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 10/162:45 pm -
1 stop7h 45m
Deal found 8/10![Southwest logo]()
$115
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.
Fri 9/257:55 pm -
1 stop11h 05m
Deal found 8/9![Southwest logo]()
$121
This Southwest deal was found by Cheapflights users on 8/6. 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 9/66:25 pm -
Nonstop2h 20m
Deal found 8/6![Southwest logo]()
$123
This Southwest deal was found by Cheapflights users on 8/7. 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 10/79:25 am -
1 stop5h 10m
Deal found 8/7![Southwest logo]()
$124
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 August 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $166 (Southwest) |
One-way from | $93 (Southwest) |
Popular in | January |
Cheapest in | September |
Average price | $367 |
Good round-trip deal | $237 or less |
Good one-way deal | $143 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 2,558,603 searches. Data last updated August 11, 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 9/19
3:10 pm-6:35 pm
Nonstop2h 25m
Boston Logan Intl
Tue 9/22
2:45 pm-8:50 pm
1 stop7h 05m
$206
Quickest round-trip
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Wed 10/14
9:10 am-12:30 pm
Nonstop2h 20m
Boston Logan Intl
Sat 10/17
7:40 am-9:15 am
Nonstop2h 35m
$227
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 9/7
5:45 am-9:00 am
Nonstop2h 15m
Boston Logan Intl
Mon 9/14
8:20 pm-10:00 pm
Nonstop2h 40m
$255
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Wed 9/23
8:40 am-4:00 pm
2 stops6h 20m
Boston Logan Intl
Sat 9/26
5:50 am-1:05 pm
2 stops8h 15m
$257
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 8/27
5:45 am-9:00 am
Nonstop2h 15m
Boston Logan Intl
Sat 8/29
4:35 pm-8:30 pm
1 stop4h 55m
$265
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Fri 10/30
12:45 pm-4:05 pm
Nonstop2h 20m
Boston Logan Intl
Mon 11/2
4:20 pm-6:05 pm
Nonstop2h 45m
$270
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sun 10/18
5:00 am-8:25 am
Nonstop2h 25m
Boston Logan Intl
Sun 10/25
10:50 pm-12:25 am
Nonstop2h 35m
$275
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 8/27
9:00 am-2:30 pm
1 stop4h 30m
Boston Logan Intl
Sun 9/6
7:55 am-5:25 pm
1 stop10h 30m
$275
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 10/29
4:20 pm-12:05 am
2 stops6h 45m
Boston Logan Intl
Mon 11/2
7:30 pm-12:05 am
1 stop5h 35m
$280
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Wed 8/19
12:50 pm-4:10 pm
Nonstop2h 20m
Boston Logan Intl
Mon 8/24
3:55 pm-5:30 pm
Nonstop2h 35m
$286
Showing 1-10 of 21 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 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 |
- 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 34 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Boston (average of $263). Flying from Chicago Midway Airport to Boston in January is currently the most expensive (average of $414). 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 August 11, 2026.
It’s optimal to fly from Chicago Midway Airport to Boston in the afternoon. By choosing this option you can save up to 12% 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 August 8, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Boston flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday at noon 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 26% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 130 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 26% 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 August 11, 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
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
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
Cambridge
Concord
Brockton
Seekonk
Cranston
Dedham
Warwick
Peabody
Auburn
Chelsea
York Beach
Londonderry
Swansea
Revere
Fitchburg
North Falmouth
Braintree
Sandwich
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Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 11, 2026.
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Midway and Boston flights
Browse other Midway and Boston flight options. Last updated on August 11, 2026.
Other flights from Midway
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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 2,558,603 searches. Data last updated August 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$126 | Average$318 | FlexibilityNo cancel fee | On-time63% |