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Midway

Cheap flights from San Diego (SAN) to Midway (MDW) - Compare and Save

SAN — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from San Diego to Chicago Midway are usually found in September or December, booked 65 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

Cheap 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 September 15, 2025.

Round-trip from

$145
(Southwest)

One-way from

$82
(Kiwi.com)

Popular in

January

Cheapest in

September

Average price

$254

Good round-trip deal

$215 or less

Good one-way deal

$179 or less
From San Diego to Chicago Midway
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One-way flight from San Diego to Chicago Midway
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Highest demand for flights based on searches. 9% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from San Diego to Chicago Midway.
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Price to beat on a one-way flight from San Diego to Chicago Midway.
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Find flight deals from San Diego to Midway

Cheapest flights from San Diego to Midway
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 September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/12. 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.
Thu 10/2311:05 amSAN - MDW
1 stop6h 30mSouthwest
Wed 10/297:00 pmMDW - SAN
1 stop6h 20mSouthwest
Deal found 9/12$145
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:30 amSAN - MDW
Nonstop4h 05mSouthwest
Sat 11/11:50 pmMDW - SAN
Nonstop4h 15mSouthwest
Deal found 9/13$153
This Priceline deal was found by Cheapflights users on 9/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/139:14 amSAN - MDW
1 stop6h 08mFrontier
Sat 11/152:57 pmMDW - SAN
1 stop7h 27mFrontier
Deal found 9/13$154
This Frontier deal was found by Cheapflights users on 9/13. 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.
Thu 11/139:14 amSAN - MDW
1 stop6h 08mFrontier
Sat 11/152:57 pmMDW - SAN
1 stop7h 27mFrontier
Deal found 9/13$155
This Southwest deal was found by Cheapflights users on 9/13. 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 10/76:30 amSAN - MDW
Nonstop4h 05mSouthwest
Tue 10/148:25 pmMDW - SAN
Nonstop4h 20mSouthwest
Deal found 9/13$163
This Southwest deal was found by Cheapflights users on 9/12. 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 10/46:55 amSAN - MDW
Nonstop4h 05mSouthwest
Tue 10/147:10 amMDW - SAN
Nonstop4h 20mSouthwest
Deal found 9/12$164
This Southwest deal was found by Cheapflights users on 9/13. 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 11/77:35 pmSAN - MDW
Nonstop3h 55mSouthwest
Mon 11/107:45 amMDW - SAN
1 stop5h 50mSouthwest
Deal found 9/13$165
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/21:18 pmSAN - MDW
1 stop6h 40mFrontier
Fri 10/106:24 pmMDW - SAN
1 stop7h 26mFrontier
Deal found 9/14$169
This Southwest deal was found by Cheapflights users on 9/13. 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 11/157:00 amSAN - MDW
Nonstop4h 00mSouthwest
Tue 11/185:15 pmMDW - SAN
1 stop5h 55mSouthwest
Deal found 9/13$170
This Frontier deal was found by Cheapflights users on 9/15. 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.
Thu 9/251:18 pmSAN - MDW
1 stop6h 40mFrontier
Fri 10/106:24 pmMDW - SAN
1 stop7h 26mFrontier
Deal found 9/15$171
This Southwest deal was found by Cheapflights users on 9/12. 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 10/410:20 amSAN - MDW
1 stop8h 00mSouthwest
Tue 10/147:10 amMDW - SAN
Nonstop4h 20mSouthwest
Deal found 9/12$174
This Southwest deal was found by Cheapflights users on 9/14. 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 10/146:30 amSAN - MDW
Nonstop4h 05mSouthwest
Fri 11/711:15 amMDW - SAN
Nonstop4h 20mSouthwest
Deal found 9/14$175

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 September 15, 2025.
Use the filters below to find and compare flights from San Diego to Chicago Midway Airport that are best for you.

Fly from

San Diego

Fly to

Midway

Route

Depart

Return

Price

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 11/12

5:00 pm-10:55 pm

Nonstop3h 55m

Chicago Midway

Sat 11/15

7:30 pm-9:50 pm

Nonstop4h 20m

$153

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 11/13

11:10 am-6:30 pm

1 stop5h 20m

Chicago Midway

Sun 11/16

7:45 am-10:10 am

Nonstop4h 25m

$169

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Sat 10/4

10:20 am-8:20 pm

1 stop8h 00m

Chicago Midway

Tue 10/14

7:10 am-9:30 am

Nonstop4h 20m

$174

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 10/29

2:05 pm-9:55 pm

1 stop5h 50m

Chicago Midway

Tue 11/4

8:20 am-10:50 am

Nonstop4h 30m

$175

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Sat 11/15

7:00 am-1:00 pm

Nonstop4h 00m

Chicago Midway

Sun 11/16

7:50 am-12:55 pm

1 stop7h 05m

$185

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Tue 10/28

6:25 pm-12:25 am

Nonstop4h 00m

Chicago Midway

Fri 10/31

11:45 am-5:15 pm

1 stop7h 30m

$185

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Tue 10/14

8:15 pm-5:15 am

1 stop7h 00m

Chicago Midway

Tue 10/21

6:05 am-10:25 am

1 stop6h 20m

$196

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Sun 10/26

6:45 pm-12:45 am

Nonstop4h 00m

Chicago Midway

Fri 10/31

7:15 pm-9:40 pm

Nonstop4h 25m

$197

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Fri 11/14

11:10 am-6:30 pm

1 stop5h 20m

Chicago Midway

Sun 11/16

11:15 am-1:35 pm

Nonstop4h 20m

$202

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 10/29

2:05 pm-9:55 pm

1 stop5h 50m

Chicago Midway

Sat 11/1

10:10 am-3:55 pm

2 stops7h 45m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 24 results
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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.
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?

Use this chart to determine the optimal time to book a round-trip flight from San Diego to Midway. Price data was last updated on September 12, 2025.

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 65 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, April is the cheapest month in which you can book a flight from San Diego to Chicago Midway Airport (average of $160). Flying from San Diego to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 15, 2025.

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 evening.

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 September 14, 2025.

Travelers seeking maximum savings on their San Diego to Chicago Midway Airport flight should consider departing on Tuesday evenings 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 September 15, 2025.
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.
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • What airport do you fly from for flights from San Diego to Chicago Midway?

    Located just 2.6 mi from the city center, San Diego is the airport most travelers will use when flying to Chicago Midway from San Diego. Booking flights from San Diego (SAN) to Chicago Midway should be relatively easy as there are 4 daily outbound flights to Chicago Midway from 2 different airlines.

  • How long is the flight from San Diego to Chicago Midway Airport?

    Airlines like Southwest fly from San Diego to Chicago Midway Airport in about 3h 55m. The time it takes to get you to your destination is usually consistent. The distance between San Diego and Chicago Midway Airport is about 1725 mi. Most flights are nonstop.

  • What are the cheapest airlines flying from San Diego to Chicago Midway Airport round-trip?

    Flying on Frontier is currently your cheapest option to Chicago Midway Airport, with prices starting at $123. Another option worth looking into is Southwest, starting at $229 round trip. You may be able to fly from San Diego to Chicago Midway Airport for 64% less than the average price by searching for these airlines.

  • What are the cheapest flights from San Diego to Chicago Midway Airport?

    On average you can expect to pay $274 for a flight from San Diego to Chicago Midway Airport. The cheapest flight overall is $88 while the most popular route, (San Diego - Chicago Midway) is currently priced at $111.

  • Can I find deals for flights from San Diego to Midway that include hotel bookings?

    Yes. In addition to deals on San Diego to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Diego to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Diego to Midway.

  • Can I find deals for business class flights from San Diego to Midway?

    Yes. Cheapflights offers flight deals from San Diego to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San Diego to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from San Diego to Chicago Midway Airport (average of $160). Flying from San Diego to Chicago Midway Airport in November is currently the most expensive (average of $249). 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.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$123Average$217FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$229Average$420FlexibilityNo cancel feeOn-time63%

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