$140+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — MDW
Sep 10 — Sep 171
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 February, booked 50 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 August 11, 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 August 11, 2026.
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.
Wed 9/910:40 pm -
1 stop6h 30m
Sat 9/121:45 pm -
1 stop5h 25m
Deal found 8/9![Southwest logo]()
$261
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:15 am -
1 stop8h 44m
Tue 9/89:29 am -
1 stop6h 40m
Deal found 8/10![Delta logo]()
$263
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 9/29:05 am -
1 stop6h 20m
Wed 9/92:05 pm -
1 stop6h 15m
Deal found 8/10![Southwest logo]()
$264
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:15 am -
1 stop8h 42m
Wed 9/161:19 pm -
1 stop7h 16m
Deal found 8/10![Delta logo]()
$265
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 9/810:40 pm -
1 stop6h 55m
Tue 9/156:50 am -
1 stop5h 45m
Deal found 8/9![Southwest logo]()
$266
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.
Sat 9/56:15 pm -
1 stop8h 45m
Fri 9/112:50 pm -
Nonstop4h 05m
Deal found 8/7![Southwest logo]()
$267
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.
Fri 9/115:50 pm -
Nonstop4h 00m
Tue 9/158:25 pm -
Nonstop4h 15m
Deal found 8/7![Southwest logo]()
$268
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:17 pm -
1 stop9h 00m
Tue 9/89:29 am -
1 stop6h 40m
Deal found 8/10![Delta logo]()
$269
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:15 am -
1 stop7h 29m
Tue 9/89:29 am -
1 stop6h 40m
Deal found 8/10![Delta logo]()
$270
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/610:17 pm -
1 stop9h 00m
Mon 9/147:13 pm -
1 stop6h 33m
Deal found 8/10![Delta logo]()
$271
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 11/168:20 am -
2 stops7h 05m
Tue 11/1710:05 am -
2 stops7h 20m
Deal found 8/10![Southwest logo]()
$273
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 August 11, 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 August 11, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:15 am -
1 stop8h 42m
Fri 9/1111:35 am -
1 stop7h 30m
Deal found 8/10![Delta logo]()
$263
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.
Sat 9/56:35 am -
Nonstop4h 00m
Wed 9/92:05 pm -
1 stop6h 15m
Deal found 8/7![Southwest logo]()
$274
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 10/3012:35 pm -
1 stop6h 00m
Sun 11/19:15 pm -
Nonstop4h 30m
Deal found 8/10![Southwest logo]()
$280
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:15 am -
1 stop7h 29m
Wed 9/231:19 pm -
1 stop7h 16m
Deal found 8/10![Delta logo]()
$297
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.
Mon 9/2110:40 pm -
1 stop6h 55m
Mon 9/288:45 pm -
Nonstop4h 15m
Deal found 8/7![Southwest logo]()
$289
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2110:20 pm -
1 stop8h 47m
Mon 9/287:13 pm -
1 stop6h 33m
Deal found 8/7![Delta logo]()
$299
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 9/810:40 pm -
1 stop6h 55m
Tue 9/1510:30 am -
2 stops6h 55m
Deal found 8/10![Southwest logo]()
$295
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2810:30 pm -
1 stop9h 19m
Wed 9/306:05 am -
1 stop8h 20m
Deal found 8/6![Delta logo]()
$299
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 9/29:05 am -
1 stop6h 20m
Wed 9/910:30 am -
2 stops6h 55m
Deal found 8/10![Southwest logo]()
$299
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 9/810:40 pm -
1 stop6h 55m
Fri 9/119:00 am -
2 stops11h 10m
Deal found 8/10![Southwest logo]()
$311
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.
Wed 9/210:40 pm -
1 stop6h 30m
Sat 9/51:45 pm -
1 stop5h 25m
Deal found 8/9![Southwest logo]()
$321
Last-minute flights from San Diego to MidwayDiscover last-minute flight deals from San Diego to Midway. Data last updated August 11, 2026 and is based on user searches.
Discover last-minute flight deals from San Diego to Midway. Data last updated August 11, 2026 and is based on user searches.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:17 pm -
1 stop9h 00m
Tue 9/89:29 am -
1 stop6h 40m
Deal found 8/10![Delta logo]()
$269
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 9/29:05 am -
1 stop6h 20m
Wed 9/92:05 pm -
1 stop6h 15m
Deal found 8/10![Southwest logo]()
$264
This Delta deal was found by Cheapflights users on 8/11. 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.
Sat 9/56:29 am -
1 stop7h 28m
Fri 9/1111:35 am -
1 stop9h 51m
Deal found 8/11![Delta logo]()
$263
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.
Sat 9/56:15 pm -
1 stop8h 45m
Fri 9/112:50 pm -
Nonstop4h 05m
Deal found 8/7![Southwest logo]()
$267
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.
Sat 9/56:35 am -
Nonstop4h 00m
Wed 9/92:05 pm -
1 stop6h 15m
Deal found 8/7![Southwest logo]()
$274
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:15 am -
1 stop7h 29m
Tue 9/156:05 am -
1 stop7h 20m
Deal found 8/10![Delta logo]()
$270
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/610:17 pm -
1 stop9h 00m
Mon 9/147:13 pm -
1 stop6h 33m
Deal found 8/10![Delta logo]()
$271
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 9/810:40 pm -
1 stop6h 55m
Tue 9/156:50 am -
1 stop5h 45m
Deal found 8/9![Southwest logo]()
$266
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.
Wed 9/910:40 pm -
1 stop6h 30m
Sat 9/121:45 pm -
1 stop5h 25m
Deal found 8/9![Southwest logo]()
$261
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:15 am -
1 stop8h 42m
Wed 9/161:19 pm -
1 stop7h 16m
Deal found 8/10![Delta logo]()
$265
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.
Fri 9/115:50 pm -
Nonstop4h 00m
Tue 9/158:25 pm -
Nonstop4h 15m
Deal found 8/7![Southwest logo]()
$268
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 August 11, 2026.
Search for one-way flight options from San Diego to Midway. Find affordable one-way fares based on user searches. Data last updated August 11, 2026.
This Southwest deal was found by Cheapflights users on 8/7. 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.
Mon 8/316:45 am -
Nonstop4h 00m
Deal found 8/7![Southwest logo]()
$140
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:25 am -
2 stops14h 22m
Deal found 8/9![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:03 pm -
2 stops18h 48m
Deal found 8/11![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:32 pm -
2 stops23h 21m
Deal found 8/11![Frontier logo]()
$147
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:54 pm -
2 stops21h 57m
Deal found 8/7![Frontier logo]()
$148
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 9/810:40 pm -
Nonstop3h 50m
Deal found 8/9![Southwest logo]()
$149
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:15 am -
1 stop8h 44m
Deal found 8/6![Delta logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/121:38 pm -
2 stops20h 21m
Deal found 8/11![Frontier logo]()
$152
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:43 pm -
2 stops35h 15m
Deal found 8/7![Frontier logo]()
$153
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:00 am -
2 stops22h 55m
Deal found 8/10![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/119:57 am -
2 stops24h 10m
Deal found 8/11![Frontier logo]()
$156
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 August 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $261 (Southwest) |
One-way from | $140 (Southwest) |
Popular in | July |
Cheapest in | December |
Average price | $357 |
Good round-trip deal | $316 or less |
Good one-way deal | $216 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 August 11, 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 San Diego - MDW Chicago Midway
SANMDW
San Diego
Wed 9/9
6:15 am-4:57 pm
1 stop8h 42m
Chicago Midway
Fri 9/11
11:35 am-5:05 pm
1 stop7h 30m
$263
Quickest round-trip
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Sat 9/5
6:35 am-12:35 pm
Nonstop4h 00m
Chicago Midway
Wed 9/9
2:05 pm-6:20 pm
1 stop6h 15m
$274
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Fri 10/30
12:35 pm-8:35 pm
1 stop6h 00m
Chicago Midway
Sun 11/1
9:15 pm-11:45 pm
Nonstop4h 30m
$280
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Mon 9/21
10:40 pm-7:35 am
1 stop6h 55m
Chicago Midway
Mon 9/28
8:45 pm-11:00 pm
Nonstop4h 15m
$289
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Tue 9/8
10:40 pm-7:35 am
1 stop6h 55m
Chicago Midway
Tue 9/15
10:30 am-3:25 pm
2 stops6h 55m
$295
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Sun 9/6
6:15 am-3:44 pm
1 stop7h 29m
Chicago Midway
Wed 9/23
1:19 pm-6:35 pm
1 stop7h 16m
$297
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Mon 9/21
10:20 pm-9:07 am
1 stop8h 47m
Chicago Midway
Mon 9/28
7:13 pm-11:46 pm
1 stop6h 33m
$299
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Mon 9/28
10:30 pm-9:49 am
1 stop9h 19m
Chicago Midway
Wed 9/30
6:05 am-12:25 pm
1 stop8h 20m
$299
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Wed 9/2
9:05 am-5:25 pm
1 stop6h 20m
Chicago Midway
Wed 9/9
10:30 am-3:25 pm
2 stops6h 55m
$299
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Tue 9/8
10:40 pm-7:35 am
1 stop6h 55m
Chicago Midway
Fri 9/11
9:00 am-6:10 pm
2 stops11h 10m
$311
Showing 1-10 of 20 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 August.
| 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 22 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 $251). Flying from San Diego to Chicago Midway Airport in July is currently the most expensive (average of $465). 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 August 11, 2026.
It’s optimal to fly from San Diego to Chicago Midway Airport at noon. By choosing this option you can save up to 20% 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 August 8, 2026.
Travelers seeking maximum savings on their San Diego to Chicago Midway Airport flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday 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 August 11, 2026.
Get a feel of what it's like to fly with Southwest 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.
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Top airline flying from San Diego to Midway
Discover the top airline 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 August 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$205 | Average$375 | FlexibilityNo cancel fee | On-time63% |