$134+ Cheap flights from San Diego (SAN) to Midway (MDW)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — MDW
Jul 1 — Jul 81
Round-trip
1 adult, Economy
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Find cheap flights from San Diego 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 San Diego to Chicago Midway are usually found in December or September, booked 65 days in advance, depart on a Wednesday or Tuesday and return on a Sunday
Cheap flight deals from San Diego to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from San Diego to MidwayExplore the most affordable flight options available from San Diego to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 1, 2026.
Explore the most affordable flight options available from San Diego to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 1, 2026.
This Southwest deal was found by Cheapflights users on 5/29. 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 9/88:15 pm
SAN
- MDW
1 stop6h 45m
Southwest
Sat 9/121:45 pm
MDW
- SAN
1 stop5h 25m
Southwest
Deal found 5/29![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 5/29. 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 9/1010:10 am
SAN
- MDW
2 stops7h 10m
Southwest
Tue 9/152:05 pm
MDW
- SAN
1 stop6h 15m
Southwest
Deal found 5/29![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 5/30. 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.
Mon 8/1710:30 pm
SAN
- MDW
1 stop9h 29m
Delta
Wed 8/196:05 am
MDW
- SAN
1 stop7h 02m
Delta
Deal found 5/30![Delta logo]()
$270
This Southwest deal was found by Cheapflights users on 5/28. 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 8/1110:55 am
SAN
- MDW
1 stop6h 20m
Southwest
Thu 8/139:00 am
MDW
- SAN
2 stops11h 10m
Southwest
Deal found 5/28![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 5/28. 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 8/2710:40 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Mon 8/312:50 pm
MDW
- SAN
Nonstop4h 05m
Southwest
Deal found 5/28![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 5/28. 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 8/2910:40 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Sat 9/51:45 pm
MDW
- SAN
1 stop5h 25m
Southwest
Deal found 5/28![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 5/29. 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 8/710:40 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Tue 8/118:25 pm
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 5/29![Southwest logo]()
$292
Best flights from San Diego to MidwayDiscover carefully curated flight deals from San Diego to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 1, 2026.
Discover carefully curated flight deals from San Diego to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 1, 2026.
This Delta deal was found by Cheapflights users on 5/28. 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 9/88:50 am
SAN
- MDW
1 stop7h 15m
Delta
Sat 9/126:00 am
MDW
- SAN
1 stop8h 45m
Delta
Deal found 5/28![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 5/31. 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 7/175:30 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Wed 7/229:05 pm
MDW
- SAN
Nonstop4h 20m
Southwest
Deal found 5/31![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 5/30. 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 8/1010:40 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Fri 8/148:45 pm
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 5/30![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 5/30. 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 7/76:15 am
SAN
- MDW
1 stop8h 00m
Delta
Sat 7/111:18 pm
MDW
- SAN
1 stop6h 56m
Delta
Deal found 5/30![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 5/31. 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 7/49:00 am
SAN
- MDW
1 stop6h 50m
Southwest
Fri 7/105:45 am
MDW
- SAN
Nonstop4h 05m
Southwest
Deal found 5/31![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 5/31. 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 6/2410:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Sat 6/278:40 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/31![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 5/29. 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 7/76:15 am
SAN
- MDW
1 stop8h 00m
Delta
Tue 7/215:10 pm
MDW
- SAN
1 stop7h 47m
Delta
Deal found 5/29![Delta logo]()
$417
This Southwest deal was found by Cheapflights users on 5/28. 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 8/137:55 am
SAN
- MDW
2 stops7h 10m
Southwest
Fri 8/142:50 pm
MDW
- SAN
Nonstop4h 05m
Southwest
Deal found 5/28![Southwest logo]()
$368
This Southwest deal was found by Cheapflights users on 5/30. 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 6/2710:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Sat 7/188:40 pm
MDW
- SAN
Nonstop4h 20m
Southwest
Deal found 5/30![Southwest logo]()
$392
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1910:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Mon 6/225:45 am
MDW
- SAN
Nonstop4h 05m
Southwest
Deal found 5/27![Southwest logo]()
$407
Last-minute flights from San Diego to MidwayDiscover last-minute flight deals from San Diego to Midway. Data last updated June 1, 2026 and is based on user searches.
Discover last-minute flight deals from San Diego to Midway. Data last updated June 1, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/30. 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 6/610:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Fri 6/199:10 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/30![Southwest logo]()
$325
This Southwest deal was found by Cheapflights users on 5/30. 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 6/136:35 am
SAN
- MDW
1 stop6h 10m
Southwest
Wed 6/176:00 am
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 5/30![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 5/30. 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 6/1310:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Tue 6/166:00 am
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 5/30![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/159:45 pm
SAN
- MDW
1 stop5h 25m
Southwest
Fri 6/199:10 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/27![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/159:45 pm
SAN
- MDW
1 stop5h 25m
Southwest
Wed 6/176:00 am
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 5/26![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 5/28. 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 6/159:45 pm
SAN
- MDW
1 stop5h 25m
Southwest
Thu 6/185:45 am
MDW
- SAN
Nonstop4h 05m
Southwest
Deal found 5/28![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 5/31. 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 6/161:02 pm
SAN
- MDW
1 stop7h 15m
Delta
Fri 6/191:26 pm
MDW
- SAN
1 stop6h 55m
Delta
Deal found 5/31![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 5/30. 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 6/1610:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Sat 6/205:40 pm
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 5/30![Southwest logo]()
$350
This Southwest deal was found by Cheapflights users on 5/28. 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 6/1910:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Mon 6/225:45 am
MDW
- SAN
Nonstop4h 05m
Southwest
Deal found 5/28![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 5/29. 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 6/1910:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Wed 6/246:00 am
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 5/29![Southwest logo]()
$342
One-way flights from San Diego to MidwaySearch for one-way flight options from San Diego to Midway. Find affordable one-way fares based on user searches. Data last updated June 1, 2026.
Search for one-way flight options from San Diego to Midway. Find affordable one-way fares based on user searches. Data last updated June 1, 2026.
This Frontier deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/206:35 am
SAN
- MDW
1 stop8h 47m
Frontier
Deal found 5/26![Frontier logo]()
$134
This Southwest deal was found by Cheapflights users on 5/28. 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 8/136:45 am
SAN
- MDW
Nonstop4h 00m
Southwest
Deal found 5/28![Southwest logo]()
$138
This Orbitz deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:35 am
SAN
- MDW
1 stop8h 16m
Frontier
Deal found 5/26![Frontier logo]()
$141
This Super.com deal was found by Cheapflights users on 5/30. 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 7/86:35 am
SAN
- MDW
1 stop7h 15m
Frontier
Deal found 5/30![Frontier logo]()
$154
This Super.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:35 am
SAN
- MDW
1 stop10h 02m
Frontier
Deal found 5/27![Frontier logo]()
$160
This Delta deal was found by Cheapflights users on 5/28. 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.
Wed 8/2610:37 am
SAN
- MDW
1 stop9h 59m
Delta
Deal found 5/28![Delta logo]()
$164
This Southwest deal was found by Cheapflights users on 5/30. 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 6/610:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Deal found 5/30![Southwest logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 5/31. 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.
Mon 8/244:17 pm
SAN
- MDW
2 stops16h 55m
Frontier
Deal found 5/31![Frontier logo]()
$167
This Southwest deal was found by Cheapflights users on 5/29. 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 6/159:45 pm
SAN
- MDW
1 stop5h 25m
Southwest
Deal found 5/29![Southwest logo]()
$169
Find flight deals from San Diego to Midway
Discover tips and strategies to find the most affordable flight options for your journey from San Diego (SAN) 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 June 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $266 (Southwest) |
One-way from | $134 (Frontier) |
Popular in | June |
Cheapest in | December |
Average price | $436 |
Good round-trip deal | $393 or less |
Good one-way deal | $188 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Diego to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 1, 2026.
Use the filters below to find and compare flights from San Diego to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Tue 9/8
8:50 am-6:05 pm
1 stop7h 15m
Chicago Midway
Sat 9/12
6:00 am-12:45 pm
1 stop8h 45m
$327
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Fri 7/17
5:30 pm-11:30 pm
Nonstop4h 00m
Chicago Midway
Wed 7/22
9:05 pm-11:25 pm
Nonstop4h 20m
$357
Quickest round-trip
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Mon 8/10
10:40 pm-4:30 am
Nonstop3h 50m
Chicago Midway
Fri 8/14
8:45 pm-10:55 pm
Nonstop4h 10m
$357
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Sat 7/4
9:00 am-5:50 pm
1 stop6h 50m
Chicago Midway
Fri 7/10
5:45 am-7:50 am
Nonstop4h 05m
$367
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Wed 6/24
10:40 pm-4:40 am
Nonstop4h 00m
Chicago Midway
Sat 6/27
8:40 pm-10:55 pm
Nonstop4h 15m
$367
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Thu 8/13
7:55 am-5:05 pm
2 stops7h 10m
Chicago Midway
Fri 8/14
2:50 pm-4:55 pm
Nonstop4h 05m
$368
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Tue 7/7
6:15 am-4:15 pm
1 stop8h 00m
Chicago Midway
Sat 7/11
1:18 pm-6:14 pm
1 stop6h 56m
$377
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Sat 6/27
10:40 pm-4:40 am
Nonstop4h 00m
Chicago Midway
Sat 7/18
8:40 pm-11:00 pm
Nonstop4h 20m
$392
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Fri 6/19
10:40 pm-4:40 am
Nonstop4h 00m
Chicago Midway
Mon 6/22
5:45 am-7:50 am
Nonstop4h 05m
$407
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Tue 7/7
6:15 am-4:15 pm
1 stop8h 00m
Chicago Midway
Tue 7/21
5:10 pm-10:57 pm
1 stop7h 47m
$417
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from San Diego 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 San Diego to Midway in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on San Diego-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 San Diego-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Diego-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Diego-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 San Diego-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 San Diego to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from San Diego with our price prediction graph.
SAN-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 San Diego to Chicago Midway Airport
How far ahead should I book a flight from San Diego to Chicago Midway Airport?
The price you pay for your flight from San Diego to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 64 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 San Diego to Chicago Midway Airport?
Currently, December is the cheapest month in which you can book a flight from San Diego to Chicago Midway Airport (average of $247). Flying from San Diego to Chicago Midway Airport in June is currently the most expensive (average of $436). 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 SAN to MDW?
Find hourly flight availability from San Diego 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 June 1, 2026.
It’s optimal to fly from San Diego to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 28% on the cost of your flight, compared to a flight in the morning.
What is the cheapest day to fly from San Diego to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from San Diego to Midway. Price data was last updated on May 30, 2026.
Travelers seeking maximum savings on their San Diego to Chicago Midway Airport flight should consider departing on Wednesday 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.
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 June 1, 2026.
Get a feel of what it's like to fly with Southwest and Frontier from San Diego to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$51 | Average$312 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$205 | Average$358 | FlexibilityNo cancel fee | On-time63% |