SAN to MDW (San Diego to Chicago) Flights

Last Minute Flights from SAN to MDW

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
SANChicagoMarch 21 to March 23$430
*Prices include taxes and fees

Cheapest SAN to MDW Flights

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
SANChicagoMay 9 to May 16$163
SANChicagoApril 28 to April 29$168
SANChicagoApril 24 to April 29$204
SANChicagoMay 6 to May 12$257
*Prices include taxes and fees
SAN to MDW Flight Details
Origin airport
San Diego Intl.
Origin airport IATA code
SAN
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Distance
1725 mi

Frequently asked questions

What airlines fly direct from SAN to Chicago Airport?
Right now, you can't fly straight between these destinations. You'll have to lock in a flight with at least one stop to make your way from SAN to Chicago Airport.
How many flights are there from SAN to MDW?
About 19 per day. If you're in a hurry to get to Chicago, see if you can score a last-minute deal from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (MDW-Midway Intl.) and then book it straight away!
How long does it take to fly from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (MDW-Midway Intl.)?
Around 5 hours and 18 minutes. On a daytime flight? Reserve a seat by a window and gaze out at the changing views. Otherwise, if you're jetting from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (MDW-Midway Intl.) when it's dark, get some shut-eye and touch down in Chicago feeling rested and refreshed.
What is the flight distance from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (MDW-Midway Intl.)?
The San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (MDW-Midway Intl.) route covers 1,750 miles (2,800 1) and is classed as a medium-haul trip. If you're seeking comfort — and you've struck a bargain — consider a premium or business class ticket.
How many morning flights are there from SAN to MDW?
Those who like to rise early can select from 58 morning flights from SAN to MDW per week.

  • You can depart as bright and early as 6:15AM if you decide to travel with Delta Air Lines (DL). This airline lists 41 weekly flights that leave before noon.
  • Frontier Airlines (F9) lists 16 morning flights per week. The earliest time you can get airborne with this carrier is 8:00AM.

How many afternoon flights are there from SAN to MDW?
Every week, you can choose between 75 afternoon and evening flights from SAN to MDW.

  • Jet off with Delta Air Lines (DL), which has 42 afternoon and evening flights every week on this route. The first departure is scheduled for 12:08PM.
  • A good alternative is Frontier Airlines (F9). Secure your seat on one of its 30 weekly afternoon and evening flights that head to MDW from 12:28PM.

What is the earliest departure time out of San Diego to Chicago?
6:15AM is the earliest flight that leaves from SAN, arriving at MDW at 6:07PM. Save precious minutes in the morning by having your luggage zipped up and ready to be tossed into your rideshare.
What is the latest departure time out of San Diego to Chicago?
The last flight takes off from SAN at 10:30PM and lands at 11:01PM at MDW. You'll have more than enough time to get ready for this flight.
What is the average price from San Diego to Chicago?
Flights from SAN to MDW can be found for around $163. You'll want to move fast, because fantastic fares don't stick around forever! This price was available on Flights.com within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

San Diego to Chicago Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from San Diego to Chicago to attend your cousin’s wedding, to pitch a business idea to your boss, or simply treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find our cheapest flights from SAN to MDW, we’ve got you covered here at Flights.com.

We present you with some of the most affordable deals on airfare, so stop that Google flights search. We want you to spend less on your flight from San Diego to Chicago, so you can spend more during your getaway. With Flights.com, you’ll find it simple to land airline tickets with itineraries matching your travel schedule. What’s more, we provide you with all the information you need to confidently make reservations on your family, business, or personal trip.

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