$142+ Cheap flights from San Diego (SAN) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — MDW
Dec 9 — Dec 161
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 January or February, booked 50 days in advance, depart on a Saturday or Wednesday 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 November 9, 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 November 9, 2026.
This Booking.com deal was found by Cheapflights users on 11/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:14 am -
2 stops20h 31m
Mon 12/1410:40 am -
2 stops23h 22m
Deal found 11/4![Frontier logo]()
$343
This Southwest deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/128:15 am -
Nonstop4h 00m
Sat 12/199:35 pm -
Nonstop4h 20m
Deal found 11/9![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 11/5. 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 12/911:25 am -
Nonstop4h 00m
Mon 12/1410:10 am -
Nonstop4h 25m
Deal found 11/5![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/58:15 am -
Nonstop4h 00m
Sat 12/1212:55 pm -
1 stop6h 50m
Deal found 11/4![Southwest logo]()
$353
This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/97:51 pm -
2 stops18h 15m
Mon 12/1410:40 am -
2 stops23h 22m
Deal found 11/4![Frontier logo]()
$356
This Southwest deal was found by Cheapflights users on 11/4. 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 12/36:30 am -
Nonstop4h 00m
Sat 12/512:55 pm -
1 stop6h 50m
Deal found 11/4![Southwest logo]()
$358
This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:05 am -
2 stops22h 40m
Mon 12/710:40 am -
2 stops23h 22m
Deal found 11/4![Frontier logo]()
$360
This Southwest deal was found by Cheapflights users on 11/6. 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.
Sat 12/58:15 am -
Nonstop4h 00m
Tue 12/83:45 pm -
Nonstop4h 30m
Deal found 11/6![Southwest logo]()
$363
This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:05 am -
2 stops22h 40m
Fri 12/115:02 pm -
2 stops19h 17m
Deal found 11/4![Frontier logo]()
$365
This Delta deal was found by Cheapflights users on 11/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/161:19 pm -
1 stop7h 35m
Sat 1/161:59 pm -
1 stop6h 54m
Deal found 11/8![Delta logo]()
$367
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 November 9, 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 November 9, 2026.
This Southwest deal was found by Cheapflights users on 11/8. 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 1/56:30 am -
Nonstop4h 00m
Tue 1/1210:00 am -
Nonstop4h 25m
Deal found 11/8![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 11/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/276:15 am -
1 stop8h 39m
Sat 1/301:41 pm -
1 stop7h 11m
Deal found 11/8![Delta logo]()
$367
This Southwest deal was found by Cheapflights users on 11/6. 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.
Sat 12/58:15 am -
Nonstop4h 00m
Tue 12/83:45 pm -
Nonstop4h 30m
Deal found 11/6![Southwest logo]()
$363
This Delta deal was found by Cheapflights users on 11/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/51:19 pm -
1 stop7h 35m
Sat 12/129:37 am -
1 stop6h 51m
Deal found 11/8![Delta logo]()
$383
This Southwest deal was found by Cheapflights users on 11/5. 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 1/1111:25 am -
1 stop6h 40m
Fri 1/159:30 pm -
Nonstop4h 25m
Deal found 11/5![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 11/7. 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.
Thu 12/316:25 am -
1 stop8h 59m
Tue 1/512:44 pm -
1 stop9h 41m
Deal found 11/7![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 11/8. 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 12/126:15 am -
2 stops9h 00m
Tue 12/159:55 am -
1 stop7h 00m
Deal found 11/8![Southwest logo]()
$372
This Southwest deal was found by Cheapflights users on 11/8. 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 12/36:30 am -
Nonstop4h 00m
Sat 12/1212:55 pm -
1 stop6h 50m
Deal found 11/8![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 11/8. 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 12/1111:45 am -
Nonstop3h 55m
Sun 12/1310:10 am -
Nonstop4h 25m
Deal found 11/8![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 11/7. 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 4/137:10 am -
2 stops6h 55m
Fri 4/163:50 pm -
Nonstop4h 25m
Deal found 11/7![Southwest logo]()
$402
This Southwest deal was found by Cheapflights users on 11/8. 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 12/38:20 am -
2 stops7h 05m
Sat 12/512:55 pm -
1 stop6h 50m
Deal found 11/8![Southwest logo]()
$404
Last-minute flights from San Diego to MidwayDiscover last-minute flight deals from San Diego to Midway. Data last updated November 9, 2026 and is based on user searches.
Discover last-minute flight deals from San Diego to Midway. Data last updated November 9, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 11/4. 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 12/36:30 am -
Nonstop4h 00m
Sat 12/512:55 pm -
1 stop6h 50m
Deal found 11/4![Southwest logo]()
$358
This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:05 am -
2 stops22h 40m
Mon 12/710:40 am -
2 stops23h 22m
Deal found 11/4![Frontier logo]()
$360
This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:05 am -
2 stops22h 40m
Fri 12/115:02 pm -
2 stops19h 17m
Deal found 11/4![Frontier logo]()
$365
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/58:15 am -
Nonstop4h 00m
Sat 12/1212:55 pm -
1 stop6h 50m
Deal found 11/4![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 11/6. 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.
Sat 12/58:15 am -
Nonstop4h 00m
Tue 12/83:45 pm -
Nonstop4h 30m
Deal found 11/6![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 11/4. 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 12/911:25 am -
Nonstop4h 00m
Mon 12/1410:10 am -
Nonstop4h 25m
Deal found 11/4![Southwest logo]()
$352
This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/97:51 pm -
2 stops18h 15m
Mon 12/1410:40 am -
2 stops23h 22m
Deal found 11/4![Frontier logo]()
$356
This Booking.com deal was found by Cheapflights users on 11/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:14 am -
2 stops20h 31m
Mon 12/1410:40 am -
2 stops23h 22m
Deal found 11/4![Frontier logo]()
$343
This Southwest deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/128:15 am -
Nonstop4h 00m
Sat 12/199:35 pm -
Nonstop4h 20m
Deal found 11/9![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 11/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/161:19 pm -
1 stop7h 35m
Tue 1/51:59 pm -
1 stop6h 54m
Deal found 11/8![Delta logo]()
$367
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 November 9, 2026.
Search for one-way flight options from San Diego to Midway. Find affordable one-way fares based on user searches. Data last updated November 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/147:06 pm -
2 stops36h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 11/8. 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.
Tue 12/158:57 am -
2 stops22h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/411:16 am -
2 stops20h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 1/66:25 pm -
2 stops37h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 11/7. 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.
Wed 1/208:37 pm -
2 stops37h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 11/9. 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.
Wed 2/38:37 pm -
2 stops25h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 2/108:37 pm -
2 stops25h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/98:57 am -
2 stops29h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$173
This Southwest deal was found by Cheapflights users on 11/8. 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 12/156:30 am -
Nonstop4h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Southwest logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 11/8. 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.
Wed 12/168:57 am -
2 stops36h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Frontier logo]()
$175
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 November 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $343 (Booking.com) |
One-way from | $142 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $572 |
Good round-trip deal | $373 or less |
Good one-way deal | $285 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 7,457,451 searches. Data last updated November 9, 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 12/9
4:05 pm-10:00 pm
Nonstop3h 55m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$174
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Thu 12/10
11:25 am-5:25 pm
Nonstop4h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Sat 12/26
10:35 pm-8:49 am
1 stop8h 14m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$184
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Wed 1/20
12:30 pm-9:05 pm
1 stop6h 35m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$184
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Tue 12/1
4:05 pm-10:00 pm
Nonstop3h 55m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$190
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Sun 12/6
6:35 am-12:35 pm
Nonstop4h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
Quickest round-trip
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Sun 11/15
10:40 pm-4:25 am
Nonstop3h 45m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Mon 11/30
10:40 pm-4:25 am
Nonstop3h 45m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Fri 12/18
10:40 pm-4:25 am
Nonstop3h 45m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
San DiegoChicago
SAN San Diego - MDW Chicago Midway
SANMDW
San Diego
Tue 11/24
10:40 pm-4:25 am
Nonstop3h 45m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
Showing 1-10 of 21 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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 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, January is the cheapest month in which you can book a flight from San Diego to Chicago Midway Airport (average of $257). Flying from San Diego to Chicago Midway Airport in November is currently the most expensive (average of $572). 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 November 9, 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 26% on the cost of your flight, compared to a flight at noon.
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 November 7, 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. Thursday 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 November 9, 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.
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
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
Merrillville
Lansing
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 7,457,451 searches. Data last updated November 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$232 | Average$412 | FlexibilityNo cancel fee | On-time63% |