$125 Find Cheap Flights from San Francisco to Chicago Midway Airport - Compare and Save

Among airlines operating San Francisco 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 Francisco and Chicago Midway Airport.

Flights from San Francisco to Chicago Midway Airport usually depart from San Francisco (SFO) 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 and a checked bag in Economy 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 Francisco to Chicago Midway Airport.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $212 round-trip via Denver Intl (DEN), compared to $397 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 Airbus A321-100/200 family is used most often on this route, operated mainly by American Airlines and United Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

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

• Atlanta Hartsfield-Jackson (ATL) - 59% of one-stop connections
• Minneapolis St Paul (MSP) - 16% of one-stop connections
• Phoenix Sky Harbor Intl (PHX) - 8% of one-stop connections
• Denver Intl (DEN) - 5% of one-stop connections

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

Yes. Being flexible with your travel dates can save you up to 34% on the San Francisco to Chicago Midway Airport route. Monday is the cheapest departure day at $339 round-trip on average, while Sunday is the most expensive at $507, a difference of $168. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Morning is the busiest departure period on San Francisco to Chicago Midway Airport flights, with 50% of flights leaving in that window. Night departures account for 50%, 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.

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

• Earliest: departs at 5:20 am and lands at 9:34 am
• Latest: departs at 11:40 pm and lands at 3:54 am.

The flight takes about 4h 14m.

Last-minute fares on this route - booked within 2 weeks of departure - run 33% above the route average of $391. Book 11 weeks before departure for the lowest fares.

A nonstop flight from San Francisco to Chicago Midway Airport takes 4h 14m, covering 1,849 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 $256 to $2,159. That means the highest observed fare was about 8x higher than the lowest one.

One-way fares from San Francisco to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $190, which is 21% below the typical average for this route.

Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 6h 40m, compared with 6h 54m via Kansas City (MCI) and 7h 16m via Phoenix Sky Harbor Intl (PHX).

Chicago Midway Airport is 2 hours ahead of San Francisco (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 Francisco to Chicago Midway Airport range from $317 to $518, with an average of $391 over the past 12 months. Anything below $317 counts as a good deal.

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