Cheap Flights from San Diego to Chicago Midway

Compare San Diego to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from San Diego to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from San Diego to Chicago Midway Airport? If you want to travel next month, return fares start from Rs71,094. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from San Diego to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like San Diego to Chicago Midway flights are currently cheapest in August.

Direct flights from San Diego to Chicago Midway

San Diego to Chicago Midway: Alternative routes

Compare routes from San Diego to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

San Diego to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs34,437
Cheapest month to flyAugust
Average flight time3 hrs, 57 mins
Most popular airlineSouthwest Airlines
Average flights per week29

Finding cheap flights from San Diego to Chicago Midway: Frequently asked questions

The best price we found for a return flight from San Diego to Chicago Midway is Rs70,892. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
3 hours and 57 minutes is the average flight time from San Diego to Chicago Midway.
Southwest Airlines flies direct from San Diego to Chicago Midway.
As of July 2026, there are 29 flights per week flying from San Diego to Chicago Midway.
The cheapest month to fly from San Diego to Chicago Midway is usually September.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from San Diego to Chicago Midway Airport on Thursday, 24 September 2026.
Yes – the average flight time is 3 hours and 57 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

The cheapest airline that flies to Chicago Midway is Southwest Airlines .

Travelling from San Diego to Chicago Midway International Airport (MDW): What you need to know

  • San Diego's main airport is San Diego International Airport (SAN). Explore your options for departing from this terminal when searching for flights from San Diego to Chicago Midway International Airport (MDW).

  • The average length of a direct San Diego to Chicago Midway International Airport flight is 3 hours 55 minutes.

  • Chicago Midway International Airport is located in Chicago. The city is in the UTC-6 timezone and is two hours ahead of San Diego.

  • With 17 direct weekly flights between the two airports, San Diego International Airport (SAN) to Chicago Midway International Airport (MDW) is the busiest route. Southwest Airlines operates the earliest flight at 6:30am. If you'd like to make the most of your day before leaving, the latest flight from SAN to MDW is with Southwest Airlines at 7:55pm.

  • Your flight from San Diego to MDW won't wait if you're late, so don't forget to check in on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're flying internationally.

  • July is a peak travel month. If you're taking off then or during a major holiday like Christmas or Thanksgiving, turn up even earlier. Aim for at least two hours ahead for domestic flights and as much as four hours for international journeys.

Airports in San Diego

San Diego International Airport (SAN)

  • San Diego International Airport (SAN) provides a hassle-free way to reach your destination. Nonstop flights from San Diego to Chicago Midway International Airport (MDW) leave from this terminal.

  • Southwest Airlines is a well-known carrier that operates direct flights from San Diego to Chicago Midway International Airport leaving from SAN.

  • The most frequently booked airline between SAN and MDW is Southwest Airlines.

  • The carrier with the best on-time performance on this route is Southwest Airlines. Its services land as planned 75.73% of the time.

  • SAN is around 5 kilometres from central San Diego. If you're ride-sharing, driving or catching a taxi from the centre, it'll take 15 minutes or so to get there, depending on traffic conditions. If you're planning to take public transport, expect the journey time to be around 25 minutes.

  • Want an easy start to your trip? Stay near San Diego International Airport. Whether you have an early flight from San Diego to Chicago Midway International Airport or want to avoid feeling rushed, these hotels are just the thing:

  • Of all flights leaving San Diego International Airport, 74% arrive on time at their destination.

  • You'll find SAN at N Harbour Dr.

McClellan-Palomar Airport (CLD)

  • CLD is roughly 48 kilometres from the centre of San Diego. Plan ahead to find the fastest way to get to your terminal.

  • Want to treat yourself to an extra night away before your San Diego to MDW flight? Kick back in a hotel near McClellan-Palomar Airport before your break officially begins. These stays are calling your name:

  • McClellan-Palomar Airport has a solid reputation for punctual service. 88% of flights taking off from here arrive right on target.

About Chicago Midway International Airport (MDW)

  • If you're arriving on a late flight from San Diego to Chicago Midway International Airport, nothing beats the convenience of staying near the terminal. Grab your bags from the carousel and then be showered and sleeping not long after at one of these hotels near MDW:

  • Booking your ride around four weeks in advance of your San Diego to Chicago Midway International Airport flight can help you get a cheaper deal.

  • The address for MDW is 5700 South Cicero.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • From Chicago Midway International Airport, central Chicago is around 16 kilometres away. It takes about 25 minutes to get to the city centre by car.

  • If you're taking public transport, expect a journey time of about 30 minutes.

How to find the cheapest flights from San Diego to Chicago Midway International Airport (MDW)

  • Rs34,437 is the best price for a one-way ticket from San Diego to Chicago Midway International Airport. Return flights start at Rs70,892. These fares can change depending on demand.

  • Book one month before your departure date. Pricing trends show that this is the ideal window for finding cheap flights from San Diego to MDW.

  • The best month for scoring cheap San Diego to Chicago Midway International Airport tickets is June. Use the 'Whole month' tool to compare flight prices, then choose the dates with the lowest fares.

  • You don't need to search every day to find out if fares have dropped when you create a Price Alert. We'll let you know the moment a better deal is available on plane tickets from San Diego to MDW.

  • Chase down a great fare on a flight from San Diego to Chicago Midway International Airport with the help of the filters. Choose your ideal arrival and departure times, airlines and number of stops. You can also sort your results by 'Fastest,' 'Cheapest' or 'Best.'

The best time to fly from San Diego to Chicago Midway International Airport (MDW)

  • July is the busiest month for flights from San Diego to Chicago Midway International Airport (MDW). Plan your visit to Chicago in November if you prefer a quieter experience.

  • When booking your San Diego to MDW plane ticket, consider the weather you're most comfortable in. July is the warmest month in Chicago, with temperatures ranging from 16ºC to 28ºC.

  • Search for cheap tickets from San Diego to Chicago Midway International Airport in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC.

More about Chicago

  • After booking your flight from San Diego to Chicago Midway International Airport, find a hotel that puts you in a great location. Make one of these accommodation options your base for exploring Chicago:

  • There are so many things to do and see in this city, it can be hard to know where to start. Millennium Park, Art Institute of Chicago and Willis Tower are highlights which should be on any well-planned Chicago itinerary.

Explore more of the United States

  • Chicago is always a good idea, but there are so many other parts of the United States you'll want to see. About 257 kilometres southeast of Chicago, a trip to Indianapolis will keep you busy. Start with leading attractions like Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

  • Around 137 kilometres north of Chicago, Milwaukee is another favourite stop in the United States. Experience major highlights starting with Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.