$139 Find Cheap Flights from San Diego to Chicago Midway Airport - Compare and Save

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.

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

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

Round-trip flights from San Diego to Chicago Midway Airport range from $266 to $457, with an average of $356 over the past 12 months. Anything below $266 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 50% above the $356 route average. Book 15 weeks before departure for the lowest fares.

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 $358 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. Other aircraft seen on the route include Boeing 737-800 Passenger/BBJ2 (winglets) variants.

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%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $297 to $2,195. That means the highest observed fare was about 7x higher than the lowest one.

JetBlue is the only airline on the San Diego to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

One-way fares from San Diego to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $146, which is 36% below the typical average for this route.

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

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

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

• Detroit Metropolitan Wayne County (DTW) - 44% of one-stop connections
• Denver Intl (DEN) - 33% of one-stop connections
• Dallas/Fort Worth (DFW) - 11% of one-stop connections
• Phoenix Sky Harbor Intl (PHX) - 11% of one-stop connections

Yes. Flexible dates can save you up to 28% on flights from San Diego to Chicago Midway Airport. Saturday is the cheapest departure day at $295 round-trip on average, while Friday is the most expensive at $405, a difference of $110.

Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

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

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.

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

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.

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 always check the fare details before booking.