$122 Find Cheap Flights from Chicago Midway Airport to Oakland - Compare and Save

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

• Earliest: departs at 9:35 am and lands at 2:19 pm
• Latest: departs at 11:05 pm and lands at 3:49 am.

The flight takes about 4h 44m.

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

A nonstop flight from Chicago Midway Airport to Oakland takes 4h 44m, covering 1,839 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 Chicago Midway Airport to Oakland range from $308 to $497, with an average of $384 over the past 12 months. Anything below $308 counts as a good deal.

On this route, nonstop and layover fares are close on average, with nonstop at $375 round-trip and layover options via Kansas City (MCI) at $367.

Southwest is the only airline operating Chicago Midway Airport to Oakland flights. 67% of its flights are on time.

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 Airbus A321neo variants.

Morning is the busiest departure period on Chicago Midway Airport to Oakland flights, with 50% of flights leaving in that window. Night departures account for 50%, 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 $243 to $1,504. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from Chicago Midway Airport to Oakland are currently lower than usual. Average one-way flight prices are about $168, which is 39% below the typical average for this route.

Oakland Airport (OAK) hosts 5 major car rental companies, with daily rates starting from around $22 for economy cars. Top options include:

• Dollar
• Thrifty
• Hertz
• Budget
• Alamo

Flights from Chicago Midway Airport to Oakland usually depart from Chicago Midway (MDW) and arrive at Oakland (OAK).

Morning flights have the fewest delays on this route, while night 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 Chicago Midway Airport to Oakland route, 33% of flights were delayed in the past 3 months, with delays averaging 2h 13m.

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

• Phoenix Sky Harbor Intl (PHX) - 60% of one-stop connections
• Denver Intl (DEN) - 20% of one-stop connections
• Kansas City (MCI) - 20% of one-stop connections

Yes. Flexible dates can save you up to 34% on flights from Chicago Midway Airport to Oakland. Saturday is the cheapest departure day at $322 round-trip on average, while Monday is the most expensive at $486, a difference of $164.

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

Only Southwest operates flights between Chicago Midway Airport and Oakland.

Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 5h 59m, compared with 6h 22m via Phoenix Sky Harbor Intl (PHX) and 6h 26m via Kansas City (MCI).

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

Some of the most popular sights in Oakland are Oakland Arena, Fox Theater and Jack London Square. These are among the most viewed places in Oakland on KAYAK.

Among airlines operating Chicago Midway Airport to Oakland 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 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.