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Midway

$80+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 Wednesday or Tuesday 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 August 14, 2025.

Round-trip from

$152
(CheapOair)

One-way from

$80
(Kiwi.com)

Popular in

January

Cheapest in

September

Average price

$334

Good round-trip deal

$228 or less

Good one-way deal

$188 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. 5% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This CheapOair deal was found by Cheapflights users on 8/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/126:35 amSAN - MDW
1 stop7h 18mFrontier
Fri 9/193:48 pmMDW - SAN
1 stop10h 05mFrontier
Deal found 8/13$152
This Priceline deal was found by Cheapflights users on 8/14. 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.
Fri 9/126:35 amSAN - MDW
1 stop7h 18mFrontier
Mon 9/154:48 pmMDW - SAN
1 stop9h 05mFrontier
Deal found 8/14$153
This Southwest deal was found by Cheapflights users on 8/13. 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 9/1010:40 amSAN - MDW
Nonstop4h 00mSouthwest
Wed 9/177:05 pmMDW - SAN
Nonstop4h 15mSouthwest
Deal found 8/13$154
This Southwest deal was found by Cheapflights users on 8/12. 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 12/25:00 pmSAN - MDW
Nonstop3h 55mSouthwest
Wed 12/38:35 pmMDW - SAN
Nonstop4h 25mSouthwest
Deal found 8/12$155
This CheapOair deal was found by Cheapflights users on 8/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1112:04 pmSAN - MDW
1 stop25h 49mFrontier
Thu 9/1810:13 amMDW - SAN
1 stop9h 29mFrontier
Deal found 8/14$157
This CheapOair deal was found by Cheapflights users on 8/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:00 pmSAN - MDW
1 stop15h 30mFrontier
Sat 11/152:57 pmMDW - SAN
1 stop7h 27mFrontier
Deal found 8/14$159
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Fri 9/266:25 amSAN - MDW
1 stop12h 27mMultiple Airlines
Mon 9/297:03 pmMDW - SAN
1 stop19h 28mMultiple Airlines
Deal found 8/12$160
This CheapOair deal was found by Cheapflights users on 8/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:11 pmSAN - MDW
1 stop13h 17mFrontier
Sun 10/51:53 pmMDW - SAN
1 stop6h 51mFrontier
Deal found 8/14$164
This Frontier deal was found by Cheapflights users on 8/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/86:35 amSAN - MDW
1 stop7h 18mFrontier
Thu 9/1110:13 amMDW - SAN
1 stop9h 29mFrontier
Deal found 8/14$167
This Southwest deal was found by Cheapflights users on 8/14. 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.
Sat 9/67:30 amSAN - MDW
Nonstop4h 00mSouthwest
Tue 9/98:20 amMDW - SAN
Nonstop4h 10mSouthwest
Deal found 8/14$169

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 14, 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

Thu 10/9

10:52 am-12:36 am

1 stop11h 44m

Chicago Midway

Fri 10/10

6:24 pm-11:50 pm

1 stop7h 26m

$152

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Fri 9/12

6:35 am-3:53 pm

1 stop7h 18m

Chicago Midway

Fri 9/19

3:48 pm-11:53 pm

1 stop10h 05m

$152

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Sun 10/5

9:03 pm-3:53 pm

1 stop16h 50m

Chicago Midway

Thu 10/9

6:24 pm-8:08 pm

1 stop27h 44m

$152

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Fri 9/12

6:35 am-3:53 pm

1 stop7h 18m

Chicago Midway

Mon 9/15

4:48 pm-11:53 pm

1 stop9h 05m

$153

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 9/10

10:40 am-4:40 pm

Nonstop4h 00m

Chicago Midway

Wed 9/17

1:35 pm-3:45 pm

Nonstop4h 10m

$154

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Tue 12/2

5:00 pm-10:55 pm

Nonstop3h 55m

Chicago Midway

Wed 12/3

8:35 pm-11:00 pm

Nonstop4h 25m

$155

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 9/11

12:04 pm-3:53 pm

1 stop25h 49m

Chicago Midway

Thu 9/18

10:13 am-5:42 pm

1 stop9h 29m

$157

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 10/2

9:03 pm-3:53 pm

1 stop16h 50m

Chicago Midway

Mon 10/6

7:15 am-5:54 pm

1 stop12h 39m

$157

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Mon 9/15

6:35 am-3:53 pm

1 stop7h 18m

Chicago Midway

Thu 9/18

10:13 am-5:42 pm

1 stop9h 29m

$157

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 10/30

6:41 am-11:30 am

1 stop26h 49m

Chicago Midway

Sun 11/2

11:21 am-6:34 pm

1 stop9h 13m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 23 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 August 8, 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 August 14, 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 30% 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 August 10, 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 August 14, 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
4,244 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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
3,217 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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.

  • 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 $121. Another option worth looking into is Southwest, starting at $247 round trip. You may be able to fly from San Diego to Chicago Midway Airport for 65% 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 $285 for a flight from San Diego to Chicago Midway Airport. The cheapest flight overall is $85 while the most popular route, (San Diego - Chicago Midway) is currently priced at $139.

  • 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$121Average$218FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$247Average$433FlexibilityNo cancel feeOn-time63%

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