$129+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — MDW
Jun 12 — Jun 191
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 May 13, 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 May 13, 2026.
This Southwest deal was found by Cheapflights users on 5/12. 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.
Tue 6/210:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Sat 6/68:40 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/12![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3010:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Sat 6/68:40 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/8![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 5/8. 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.
Wed 6/310:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Tue 6/96:00 am
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 5/8![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 5/12. 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.
Tue 6/210:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Thu 6/49:10 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/12![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 5/10. 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.
Sun 5/3110:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Sat 6/68:40 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/10![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 5/12. 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.
Tue 6/210:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Sun 6/76:05 am
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 5/12![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 5/12. 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.
Tue 6/910:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Tue 6/169:05 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/12![Southwest logo]()
$307
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 May 13, 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 May 13, 2026.
This Southwest deal was found by Cheapflights users on 5/8. 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.
Tue 6/210:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Thu 6/42:15 pm
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 5/8![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/510:53 am
SAN
- MDW
1 stop8h 16m
Delta
Sat 6/65:30 pm
MDW
- SAN
1 stop7h 58m
Delta
Deal found 5/11![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 5/10. 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.
Sun 5/3110:40 pm
SAN
- MDW
1 stop6h 15m
Southwest
Sat 6/68:40 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/10![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 5/11. 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.
Wed 6/310:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Wed 6/109:05 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/11![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 5/10. 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 7/1310:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Fri 7/179:10 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/10![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/154:25 pm
SAN
- MDW
1 stop5h 40m
Southwest
Sun 7/196:05 am
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 5/12![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:05 pm
SAN
- MDW
1 stop7h 00m
Southwest
Mon 7/209:10 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/12![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 5/12. 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 7/258:05 pm
SAN
- MDW
1 stop6h 55m
Southwest
Wed 7/295:25 pm
MDW
- SAN
1 stop6h 05m
Southwest
Deal found 5/12![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 5/8. 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 8/77:55 am
SAN
- MDW
2 stops7h 10m
Southwest
Mon 8/105:40 am
MDW
- SAN
1 stop6h 40m
Southwest
Deal found 5/8![Southwest logo]()
$378
This Southwest deal was found by Cheapflights users on 5/8. 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 6/269:25 pm
SAN
- MDW
1 stop6h 00m
Southwest
Tue 6/305:50 pm
MDW
- SAN
2 stops7h 00m
Southwest
Deal found 5/8![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 5/8. 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 7/3010:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Mon 8/39:10 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/8![Southwest logo]()
$392
Last-minute flights from San Diego to MidwayDiscover last-minute flight deals from San Diego to Midway. Data last updated May 13, 2026 and is based on user searches.
Discover last-minute flight deals from San Diego to Midway. Data last updated May 13, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/7. 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.
Sat 5/3010:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Sat 6/68:40 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/7![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 5/10. 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.
Sun 5/3110:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Sat 6/68:40 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/10![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 5/11. 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.
Tue 6/28:30 pm
SAN
- MDW
1 stop6h 30m
Southwest
Sat 6/68:40 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/11![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 5/11. 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.
Tue 6/210:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Thu 6/45:45 am
MDW
- SAN
Nonstop4h 05m
Southwest
Deal found 5/11![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 5/11. 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.
Tue 6/210:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Mon 6/89:10 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 5/11![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 5/8. 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.
Wed 6/310:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Tue 6/97:00 am
MDW
- SAN
1 stop6h 05m
Southwest
Deal found 5/8![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 5/10. 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 6/910:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Tue 6/166:00 am
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 5/10![Southwest logo]()
$307
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 May 13, 2026.
Search for one-way flight options from San Diego to Midway. Find affordable one-way fares based on user searches. Data last updated May 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:25 am
SAN
- MDW
2 stops37h 37m
Frontier
Deal found 5/10![Frontier logo]()
$129
This Trip.com deal was found by Cheapflights users on 5/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:25 am
SAN
- MDW
1 stop6h 50m
Frontier
Deal found 5/9![Frontier logo]()
$131
This Southwest deal was found by Cheapflights users on 5/7. 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.
Tue 6/29:35 pm
SAN
- MDW
1 stop5h 25m
Southwest
Deal found 5/7![Southwest logo]()
$134
This Southwest deal was found by Cheapflights users on 5/9. 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 6/68:25 pm
SAN
- MDW
1 stop7h 00m
Southwest
Deal found 5/9![Southwest logo]()
$139
This Trip.com deal was found by Cheapflights users on 5/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:25 am
SAN
- MDW
1 stop8h 17m
Frontier
Deal found 5/11![Frontier logo]()
$143
This Super.com deal was found by Cheapflights users on 5/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/146:25 am
SAN
- MDW
1 stop6h 50m
Frontier
Deal found 5/8![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/38:29 pm
SAN
- MDW
2 stops23h 39m
Frontier
Deal found 5/8![Frontier logo]()
$153
This Southwest deal was found by Cheapflights users on 5/8. 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 6/110:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 5/8![Southwest logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/41:38 pm
SAN
- MDW
2 stops19h 31m
Frontier
Deal found 5/12![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/99:43 am
SAN
- MDW
2 stops34h 28m
Frontier
Deal found 5/12![Frontier logo]()
$157
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 May 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $247 (Southwest) |
One-way from | $129 (Kiwi.com) |
Popular in | June |
Cheapest in | December |
Average price | $288 |
Good round-trip deal | $371 or less |
Good one-way deal | $238 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 May 13, 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
Quickest round-trip
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Tue 6/2
10:40 pm-4:35 am
Nonstop3h 55m
Chicago Midway
Thu 6/4
2:15 pm-4:25 pm
Nonstop4h 10m
$277
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Sun 5/31
10:40 pm-6:55 am
1 stop6h 15m
Chicago Midway
Sat 6/6
8:40 pm-10:55 pm
Nonstop4h 15m
$292
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Fri 6/5
10:53 am-9:09 pm
1 stop8h 16m
Chicago Midway
Sat 6/6
5:30 pm-11:28 pm
1 stop7h 58m
$297
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Wed 6/3
10:40 pm-4:35 am
Nonstop3h 55m
Chicago Midway
Wed 6/10
9:05 pm-11:20 pm
Nonstop4h 15m
$332
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Mon 7/13
10:40 pm-4:40 am
Nonstop4h 00m
Chicago Midway
Fri 7/17
9:10 pm-11:25 pm
Nonstop4h 15m
$357
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Wed 7/15
4:25 pm-12:05 am
1 stop5h 40m
Chicago Midway
Sun 7/19
6:05 am-8:15 am
Nonstop4h 10m
$367
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Wed 7/15
3:05 pm-12:05 am
1 stop7h 00m
Chicago Midway
Mon 7/20
9:10 pm-11:25 pm
Nonstop4h 15m
$367
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Sat 7/25
8:05 pm-5:00 am
1 stop6h 55m
Chicago Midway
Wed 7/29
5:25 pm-9:30 pm
1 stop6h 05m
$377
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Fri 8/7
7:55 am-5:05 pm
2 stops7h 10m
Chicago Midway
Mon 8/10
5:40 am-10:20 am
1 stop6h 40m
$378
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Fri 6/26
9:25 pm-5:25 am
1 stop6h 00m
Chicago Midway
Tue 6/30
5:50 pm-10:50 pm
2 stops7h 00m
$387
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 May.
| 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
Prices
Airlines
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 $432). 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 May 13, 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 29% 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 9, 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 May 13, 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.
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Related info for your journey
Find useful and relevant information for your journey from San Diego to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Top 2 airlines flying from San Diego to Midway
Discover the top 2 airlines that operate flights from San Diego to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$51 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$205 | Average$348 | FlexibilityNo cancel fee | On-time63% |