$124 Find Cheap Flights from Chicago Midway Airport to San Diego - Compare and Save

Among airlines operating Chicago Midway Airport to San Diego flights:

• Southwest: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Only Southwest operates flights between Chicago Midway Airport and San Diego.

Flights from Chicago Midway Airport to San Diego usually depart from Chicago Midway (MDW) and arrive at San Diego (SAN).

Here are some options for this route, based on selected ticket types and cabin classes:

• Southwest: a cabin bag and a checked bag in Economy Class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Only Economy Class is available on flights from Chicago Midway Airport to San Diego.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $186 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $322 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest and American Airlines. Other aircraft seen on the route include Airbus A321-100/200 variants.

One-stop flights from Chicago Midway Airport to San Diego most commonly connect through:

• Atlanta Hartsfield-Jackson (ATL) - 25% of one-stop connections
• Denver Intl (DEN) - 25% of one-stop connections
• Detroit Metropolitan Wayne County (DTW) - 25% of one-stop connections
• Phoenix Sky Harbor Intl (PHX) - 25% of one-stop connections

Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

On the Chicago Midway Airport to San Diego route, being flexible with your departure day can save you up to 20%. Sunday is the cheapest day at $287 round-trip on average, while Wednesday is the most expensive at $357: a $70 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

Morning is the busiest departure period on Chicago Midway Airport to San Diego flights, with 34% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 33%, and night flights for 0%.

Some of the most popular sights in San Diego are Gaslamp Quarter, San Diego Convention Center and SeaWorld San Diego. These are among the most viewed places in San Diego on KAYAK.

These are the earliest and latest flight times available from Chicago Midway Airport to San Diego:

• Earliest: departs at 5:25 am and lands at 9:43 am
• Latest: departs at 9:35 pm and lands at 1:53 am.

The flight takes about 4h 18m.

Last-minute fares on this route - booked within 2 weeks of departure - run 43% above the route average of $322. Book 22 weeks before departure for the lowest fares.

A nonstop flight from Chicago Midway Airport to San Diego takes 4h 18m, covering 1,725 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $247 to $2,321. That means the highest observed fare was about 9x higher than the lowest one.

One-way fares from Chicago Midway Airport to San Diego are currently lower than usual. Average one-way flight prices are about $128, which is 41% below the typical average for this route.

Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 6h 09m, compared with 6h 56m via Phoenix Sky Harbor Intl (PHX) and 8h 13m via Atlanta Hartsfield-Jackson (ATL).

San Diego is 2 hours behind Chicago Midway Airport (Pacific Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

San Diego Airport (SAN) hosts 5 major car rental companies, with daily rates starting from around $14 for economy cars. Top options include:
· Dollar
· Payless
· Europcar
· Thrifty
· Fox

Round-trip flights from Chicago Midway Airport to San Diego range from $243 to $411, with an average of $322 over the past 12 months. Anything below $243 counts as a good deal.