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Midway

$86+ 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — MDW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from San Diego to Chicago Midway are usually found in December or April, booked 62 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 July 3, 2025.

Round-trip from

$168
(Priceline)

One-way from

$94
(Priceline)

Popular in

January

Cheapest in

December

Average price

$340

Good round-trip deal

$279 or less

Good one-way deal

$208 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 ($19 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 July 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 July 3, 2025.

This Priceline deal was found by Cheapflights users on 7/2. 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 8/1410:52 amSAN - MDW
1 stop8h 02mFrontier
Sat 8/162:44 pmMDW - SAN
1 stop10h 18mFrontier
Deal found 7/2$168
This Southwest deal was found by Cheapflights users on 7/3. 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 8/237:30 amSAN - MDW
Nonstop4h 00mSouthwest
Sat 8/308:25 amMDW - SAN
Nonstop4h 15mSouthwest
Deal found 7/3$171

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 July 3, 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 8/14

10:52 am-8:54 pm

1 stop8h 02m

Chicago Midway

Sat 8/16

2:44 pm-11:02 pm

1 stop10h 18m

$168

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Sat 8/23

7:30 am-1:30 pm

Nonstop4h 00m

Chicago Midway

Wed 8/27

7:05 pm-9:20 pm

Nonstop4h 15m

$171

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Fri 8/1

10:15 pm-8:44 am

1 stop8h 29m

Chicago Midway

Fri 8/8

12:43 pm-7:56 pm

1 stop9h 13m

$257

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 9/3

8:00 am-1:55 pm

Nonstop3h 55m

$86

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Tue 8/12

8:00 am-5:03 pm

1 stop7h 03m

$94

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Fri 9/26

6:15 am-8:52 pm

1 stop12h 37m

$106

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Fri 8/1

10:30 pm-9:45 am

1 stop9h 15m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

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 June 27, 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 62 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 July 3, 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 29% 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 June 29, 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 July 3, 2025.
Get a feel of what it's like to fly with Southwest, Delta, 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
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Frontier
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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 2 daily outbound flights to Chicago Midway from 3 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 $168. Additional round-trip tickets that might be worth considering are offered by Southwest and Delta, with the lowest prices starting at $171 and $257, respectively. You may be able to fly from San Diego to Chicago Midway Airport for 53% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from San Diego to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $94 on Frontier. Other airlines that offer cheap prices include Southwest from $96 and Delta from $129 one-way.

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

    On average you can expect to pay $300 for a flight from San Diego to Chicago Midway Airport. The cheapest flight overall is $128 while the most popular route, (San Diego - Chicago Midway) is currently priced at $171.

  • 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 San Diego?

Book flights to San Diego if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for San Diego to Midway

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Top 3 airlines flying from San Diego to Midway

Discover the top 3 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$121Average$223FlexibilityNo cancel feeOn-time62%
DeltaCheapest$258Average$302FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$284Average$448FlexibilityNo cancel feeOn-time63%

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