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

Among airlines operating Oakland 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 Oakland and Chicago Midway Airport.

Flights from Oakland to Chicago Midway Airport usually depart from Oakland (OAK) 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

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 Oakland to Chicago Midway Airport.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $340 round-trip via San Diego (SAN), compared to $483 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 737-800 Passenger/BBJ2 (winglets) family is used most often on this route, operated mainly by Southwest. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

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

• Las Vegas Harry Reid Intl (LAS) - 43% of one-stop connections
• Phoenix Sky Harbor Intl (PHX) - 30% of one-stop connections
• Denver Intl (DEN) - 17% of one-stop connections
• Los Angeles (LAX) - 4% of one-stop connections

Las Vegas Harry Reid Intl (LAS) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 18% on the Oakland to Chicago Midway Airport route. Wednesday is the cheapest departure day at $398 round-trip on average, while Tuesday is the most expensive at $484, a difference of $86. 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 Oakland 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 Oakland to Chicago Midway Airport:

• Earliest: departs at 5:10 am and lands at 9:12 am
• Latest: departs at 11:55 pm and lands at 3:57 am.

The flight takes about 4h 02m.

Last-minute fares on this route - booked within 2 weeks of departure - run 33% above the route average of $451. Book 20 weeks before departure for the lowest fares.

A nonstop flight from Oakland to Chicago Midway Airport takes 4h 02m, 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 $241 to $1,557. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from Oakland to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $136, which is 47% below the typical average for this route.

Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 6h 04m, compared with 6h 20m via Las Vegas Harry Reid Intl (LAS) and 6h 24m via Los Angeles (LAX).

Chicago Midway Airport is 2 hours ahead of Oakland (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 Oakland to Chicago Midway Airport range from $362 to $571, with an average of $451 over the past 12 months. Anything below $362 counts as a good deal.