$116 Find Cheap Flights from Chicago Midway Airport to Oakland - Compare and Save

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.

Only Southwest operates flights between Chicago Midway Airport and Oakland.

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

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 travelers should check the fare details before booking.

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

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $367 round-trip via Kansas City (MCI), compared to $393 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 variants.

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

• Denver Intl (DEN) - 38% of one-stop connections
• Phoenix Sky Harbor Intl (PHX) - 38% of one-stop connections
• Las Vegas Harry Reid Intl (LAS) - 13% of one-stop connections
• Kansas City (MCI) - 13% of one-stop connections

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

On the Chicago Midway Airport to Oakland route, being flexible with your departure day can save you up to 36%. Saturday is the cheapest day at $312 round-trip on average, while Monday is the most expensive at $486: a $174 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

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, 32% of flights were delayed in the past 3 months, with delays averaging 2 hours 15 minutes.

Morning is the busiest departure period on Chicago Midway Airport to Oakland flights, with 100% of flights leaving in that window. Afternoon departures account for 0%, evening flights for 0%, and night flights for 0%.

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.

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

• Earliest: departs at 9:35 am and lands at 2:15 pm
• Latest: departs at 11:05 pm and lands at 3:45 am.

The flight takes about 4h 40m.

A nonstop flight from Chicago Midway Airport to Oakland takes 4h 40m, 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.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $231 to $1,860. That means the highest observed fare was about 8x 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 $120, which is 58% below the typical average for this route.

Southwest is the only airline operating Chicago Midway Airport to Oakland flights. 68% of its flights are on time.

Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 5h 50m, 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.

Oakland Airport (OAK) hosts 5 major car rental companies, with daily rates starting from around $21 for economy cars. Top options include:
• Dollar
• Thrifty
• Budget
• Hertz
• Alamo

Round-trip flights from Chicago Midway Airport to Oakland range from $311 to $533, with an average of $397 over the past 12 months. Anything below $311 counts as a good deal.