$131 Find Cheap Flights from San Diego to Chicago Midway Airport - Compare and Save

Among airlines operating San Diego to Chicago Midway Airport flights:

• Southwest: offers free seat selection

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

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

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

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

• Southwest: a cabin bag in Economy Class class
• JetBlue: a cabin bag in Economy Class 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 San Diego to Chicago Midway Airport.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $109 round-trip via Phoenix Sky Harbor Intl (PHX), compared to $332 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 Boeing 737-800 Passenger/BBJ2 (winglets) variants.

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

• Denver Intl (DEN) - 50% of one-stop connections
• Detroit Metropolitan Wayne County (DTW) - 33% of one-stop connections
• Phoenix Sky Harbor Intl (PHX) - 17% of one-stop connections

Denver Intl (DEN) handles the largest share of one-stop connections on this route.

On the San Diego to Chicago Midway Airport route, being flexible with your departure day can save you up to 27%. Saturday is the cheapest day at $282 round-trip on average, while Monday is the most expensive at $382: a $100 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

Morning is the busiest departure period on San Diego to Chicago Midway Airport flights, with 67% of flights leaving in that window. Night departures account for 33%, afternoon flights for 0%, and evening flights for 0%.

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

A nonstop flight from San Diego to Chicago Midway Airport takes 3h 54m, covering 1,725 miles.

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

• Earliest: departs at 6:15 am and lands at 10:09 am
• Latest: departs at 10:40 pm and lands at 2:34 am.

The flight takes about 3h 54m.

Last-minute fares on this route - booked within 2 weeks of departure - run 78% above the route average of $323. Book 15 weeks before departure for the lowest fares.

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 $259 to $2,487. That means the highest observed fare was about 10x higher than the lowest one.

One-way fares from San Diego to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $136, which is 38% below the typical average for this route.

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 7h 51m, compared with 8h 08m via Phoenix Sky Harbor Intl (PHX) and 8h 21m via Denver Intl (DEN).

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

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
· Hertz
· Dollar
· Budget
· Alamo
· Rent-A-Wreck

Round-trip flights from San Diego to Chicago Midway Airport range from $246 to $443, with an average of $323 over the past 12 months. Anything below $246 counts as a good deal.