$100 Find Cheap Flights from Oakland to Chicago Midway Airport - Compare and Save

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.

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

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.

Round-trip flights from Oakland to Chicago Midway Airport range from $356 to $564, with an average of $442 over the past 12 months. Anything below $356 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 35% above the $442 route average. Book 11 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $360 round-trip via Los Angeles (LAX), compared to $475 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 Passenger/BBJ2 (winglets) variants.

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%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $243 to $1,990. That means the highest observed fare was about 8x 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 $126, which is 51% below the typical average for this route.

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

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

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

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

• Las Vegas Harry Reid Intl (LAS) - 33% of one-stop connections
• Phoenix Sky Harbor Intl (PHX) - 29% of one-stop connections
• Denver Intl (DEN) - 19% of one-stop connections
• San Diego (SAN) - 10% of one-stop connections

Yes. Flexible dates can save you up to 22% on flights from Oakland to Chicago Midway Airport. Saturday is the cheapest departure day at $375 round-trip on average, while Friday is the most expensive at $480, a difference of $105.

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

Only Southwest operates flights between Oakland and Chicago Midway Airport.

Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 6h 04m, compared with 6h 07m via Hollywood Burbank (BUR) and 6h 08m via Las Vegas Harry Reid Intl (LAS).

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.

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

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.

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.