Midway

$71+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — MDW
Nov 25 — Dec 21
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The best prices from San Diego to Chicago Midway are usually found in February or July, booked 67 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 November 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

October

Cheapest in

February

Round-trip from

$140
(Kiwi.com)

One-way from

$71
(Cheapflightsfares)
Provider with most accurate pricing for San Diego-Chicago Midway flight deals.
Provider most trusted by Cheapflights users for San Diego-Chicago Midway flights.
High demand for flights, 28% potential price rise
Best time to find cheap flights, 42% potential price drop
From San Diego to Chicago Midway
One-way flight from San Diego to Chicago Midway

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 November 20, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/20. 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 12/510:35 amSAN - MDW
1 stop23h 13mFrontier
Mon 12/912:43 pmMDW - SAN
1 stop8h 27mFrontier
Deal found 11/20$140
This Kissandfly.com deal was found by Cheapflights users on 11/19. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/125:09 pmSAN - MDW
2 stops16h 39mMultiple Airlines
Mon 12/167:15 amMDW - SAN
3 stops13h 55mMultiple Airlines
Deal found 11/19$310
This Delta deal was found by Cheapflights users on 11/19. 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 12/126:15 amSAN - MDW
1 stop8h 46mDelta
Sat 12/149:30 amMDW - SAN
1 stop6h 57mDelta
Deal found 11/19$320
This Southwest deal was found by Cheapflights users on 11/18. 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 12/244:50 pmSAN - MDW
Nonstop3h 50mSouthwest
Wed 1/88:40 amMDW - SAN
Nonstop4h 40mSouthwest
Deal found 11/18$395

Find flights from San Diego to Midway within your budget

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 12/5

10:35 am-11:48 am

1 stop23h 13m

Chicago Midway

Mon 12/9

12:43 pm-7:10 pm

1 stop8h 27m

$140

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 12/12

5:09 pm-11:48 am

2 stops16h 39m

Chicago Midway

Mon 12/16

7:15 am-7:10 pm

3 stops13h 55m

$310

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 12/12

6:15 am-5:01 pm

1 stop8h 46m

Chicago Midway

Sat 12/14

9:30 am-2:27 pm

1 stop6h 57m

$320

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Tue 12/24

4:50 pm-10:40 pm

Nonstop3h 50m

Chicago Midway

Wed 1/8

8:40 am-11:20 am

Nonstop4h 40m

$395

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Fri 1/10

3:07 pm-11:35 pm

1 stop6h 28m

$71

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 12/26

6:15 am-7:32 pm

2 stops35h 17m

$138

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Tue 3/18

10:10 pm-8:51 am

1 stop8h 41m

$150

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Tue 12/24

4:50 pm-10:40 pm

Nonstop3h 50m

$196

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Fri 1/17

12:35 pm-10:36 am

3 stops20h 01m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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.

Travel insights for flights from San Diego to Midway

Get recent, data-driven insights about flights from San Diego to Midway including ideal travel times, pricing trends, and more.

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 November 15, 2024.

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 67 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 $159). Flying from San Diego to Chicago Midway Airport in July is currently the most expensive (average of $231). 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 20, 2024.

It’s optimal to fly from San Diego to Chicago Midway Airport in the evening. By choosing this option you can save up to 35% on the cost of your flight, compared to a flight in the afternoon.

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 10, 2024.

Travelers seeking maximum savings on their San Diego to Chicago Midway Airport flight should consider departing on Monday evenings 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 20, 2024.
Read through reviews of airlines operating flights from San Diego to Chicago, such as Delta, Southwest and Frontier. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

8.1
Very good
5,014 reviews
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

8.0
Very good
8,756 reviews
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

7.3
Good
2,811 reviews
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

6.1
Okay
3,539 reviews
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

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 $140. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $320 and $395, respectively. You may be able to fly from San Diego to Chicago Midway Airport for 48% 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 $71 on Frontier. Other airlines that offer cheap prices include Southwest from $196 and Delta from $219 one-way.

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

    On average you can expect to pay $419 for a flight from San Diego to Chicago Midway Airport. The cheapest flight overall is $153 while the most popular route, (San Diego - Chicago Midway) is currently priced at $138.

  • 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, December is the cheapest month in which you can book a flight from San Diego to Chicago Midway Airport (average of $159). Flying from San Diego to Chicago Midway Airport in July is currently the most expensive (average of $231). 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.

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Alternative routes for San Diego to Midway

See prices for flight routes from nearby airports that may be better suited for you.

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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$226FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$252Average$485FlexibilityNo cancel feeOn-time63%
DeltaCheapest$258Average$386FlexibilityNo cancel feeOn-timeN/A
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