$123 Find Cheap Flights from San Diego to Chicago - Compare and Save

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

• Earliest: departs at 6:15 am and lands at 10:28 am
• Latest: departs at 10:56 pm and lands at 3:09 am.

The flight takes about 4h 13m.

Three cabin classes are available on flights from San Diego to Chicago:

• Economy Class
• Business Class
• First Class

A nonstop flight from San Diego to Chicago takes 4h 13m, covering 1,732 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 range from $240 to $413, with an average of $324 over the past 12 months. Anything below $240 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 44% above the $324 route average. Book 18 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $232 round-trip via Chicago O'Hare Intl (ORD), compared to $327 for nonstop.

United Airlines is slightly above the route average for timely arrivals, while American Airlines has a lower on-time arrival rate. On-time arrival rates on San Diego to Chicago flights are:

• United Airlines: 94% on time
• American Airlines: 90% on time
• Alaska Airlines: 88% on time

Overall, flights on this route are punctual 91% of the time on average.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Morning is the busiest departure period on San Diego to Chicago flights, with 51% of flights leaving in that window. Afternoon departures account for 25%, night flights for 18%, and evening flights for 6%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $246 to $2,269. That means the highest observed fare was about 9x higher than the lowest one.

Three airlines offer in-flight Wi-Fi on San Diego to Chicago flights:

• American Airlines
• Alaska Airlines
• JetBlue

Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

One-way fares from San Diego to Chicago are currently lower than usual. Average one-way flight prices are about $128, which is 35% below the typical average for this route.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Dollar
• Ace

Near Chicago Midway Airport (MDW) — daily rates from around $32:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

Flights from San Diego to Chicago usually depart from San Diego (SAN) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

Night flights have the fewest delays on this route, while evening departures tend to have the most.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the San Diego to Chicago route, 9% of flights were delayed in the past 3 months, with delays averaging 3h 08m.

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

• Denver Intl (DEN) - 49% of one-stop connections
• Phoenix Sky Harbor Intl (PHX) - 17% of one-stop connections
• Dallas/Fort Worth (DFW) - 12% of one-stop connections
• Las Vegas Harry Reid Intl (LAS) - 9% of one-stop connections

Yes. Flexible dates can save you up to 18% on flights from San Diego to Chicago. Saturday is the cheapest departure day at $299 round-trip on average, while Sunday is the most expensive at $362, a difference of $63.

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

4 airlines operate flights between San Diego and Chicago. The airlines offering nonstop flights on this route include:

• American Airlines
• United Airlines
• Southwest
• Alaska Airlines

Flying via Chicago O'Hare Intl (ORD) gives the shortest average 1-stop total travel time at 6h 52m, compared with 7h 04m via Los Angeles (LAX) and 7h 51m via Detroit Metropolitan Wayne County (DTW).

Chicago 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 are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

Among airlines operating San Diego to Chicago flights:

• American Airlines: offers extra legroom; offers free seat selection
• Alaska Airlines: offers extra legroom; offers free seat selection
• United Airlines: offers extra legroom; offers free seat selection
• 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:

• American Airlines: a cabin bag and a checked bag in Economy Class
• Alaska Airlines: a cabin bag and a checked bag in Economy Class
• United Airlines: a cabin bag and a checked bag in Economy Class

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

All of the major rental car companies have locations at the Multi-Modal Facility located offsite from the airport. Dedicated shuttle buses run 24/7 from the airport terminals to the facility. Pickup locations for the shuttle buses are clearly marked with locations just outside of the terminal baggage claim areas.

There are several nonstop flight choices from Chicago to San Diego. Southwest Airlines offers nonstop service to Chicago Midway Airport (MDW), while both United Airlines and American Airlines offer nonstop service to Chicago O'Hare International Airport (ORD).

The Chicago Transit Authority offers a train service from the airport. The Blue Line train operates on a 24h basis, making several stops on the way, with both the Clinton and Grand stops being great places to hop off the train in Downtown Chicago.

The Chicago Transit Authority's Orange Line offers service to Chicago Midway Airport. The trains run from early morning until after midnight every day. The trip to Downtown Chicago from the airport takes roughly 25min. The Roosevelt Station is a great place to hop off the train to explore Downtown Chicago.