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Cheap Flights from Chicago Midway to Oakland Metropolitan Oak

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      Travellers and cabin class, 1 Adult, Economy
      Southwest Airlines

      Compare Chicago Midway to Oakland Metropolitan Oak flight deals

      Find the cheapest month or even day of the year to fly to Oakland Metropolitan Oak

      Book the best Oakland Metropolitan Oak fare with no extra fees

      Flight deals from Chicago Midway to Oakland Metropolitan Oak

      Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Oakland Metropolitan Oak Airport? If you want to travel next month, return fares start from R 3,946. Find the lowest prices on one-way and return tickets right here.
      Oakland.R 1,894 per passenger.Departing Sat, 24 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 24 Oct, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 1,894, select.
      Oakland.R 1,895 per passenger.Departing Thu, 5 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 5 Nov, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 1,895, select.
      Oakland.R 1,895 per passenger.Departing Wed, 23 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 23 Sep, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 1,895, select.
      Oakland.R 1,896 per passenger.Departing Sat, 9 Jan.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 9 Jan, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 1,896, select.
      Oakland.R 1,896 per passenger.Departing Thu, 3 Dec.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 3 Dec, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 1,896, select.
      Oakland.R 2,552 per passenger.Departing Thu, 11 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 11 Feb, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 2,552, select.
      Oakland.R 3,869 per passenger.Departing Sat, 29 Aug.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 29 Aug, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 3,869, select.
      Oakland.R 4,172 per passenger.Departing Sat, 29 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 29 Aug, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From R 4,172, select.

      Find the cheapest month to fly from Chicago Midway to Oakland Metropolitan Oak

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Oakland Metropolitan Oak flights are currently cheapest in October.
      Aug
      from R 3,869
      Sep
      from R 1,895
      Oct
      from R 1,894
      Nov
      from R 1,895
      Dec
      from R 1,896
      Jan
      from R 1,896
      Feb
      from R 2,552
      Mar
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      Apr
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      May
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      Jun
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      Jul
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      Direct flights from Chicago Midway to Oakland Metropolitan Oak

      Southwest Airlines

      Chicago Midway to Oakland Metropolitan Oak: Alternative routes

      Compare routes from Chicago Midway to Oakland below. You may find an airport to fly into that's cheaper, faster, or easier than Oakland Metropolitan Oak.

      Oakland Metropolitan Oak

      10km from central Oakland
      Closest
      from R 1,894
      Search flights

      San Francisco International

      23km from central Oakland
      Cheapest
      from R 1,274
      Search flights

      Concord

      28km from central Oakland
      Search flights

      San Jose International

      57km from central Oakland
      from R 1,894
      Search flights

      San Jose Reid-Hillview

      66km from central Oakland
      Search flights

      Chicago to Oakland: Flight information

      The things to know before you go.
      Cheapest flight foundR 1,894
      Cheapest month to flyOctober
      Average flight time4 hrs, 40 mins
      Most popular airlineSouthwest Airlines
      Average flights per week14

      Finding cheap flights from Chicago Midway to Oakland Metropolitan Oak: Frequently asked questions

      The best price we found for a return flight from Chicago Midway to Oakland Metropolitan Oak is R 3,795. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      4 hours and 40 minutes is the average flight time from Chicago Midway to Oakland Metropolitan Oak.
      Southwest Airlines flies direct from Chicago Midway to Oakland Metropolitan Oak.
      As of August 2026, there are 14 flights per week flying from Chicago Midway to Oakland Metropolitan Oak.
      The cheapest month to fly from Chicago Midway to Oakland Metropolitan Oak is usually December.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Oakland Metropolitan Oak Airport on Tuesday, 8 December 2026.
      Yes – the average flight time is 4 hours and 40 minutes.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Oakland Metropolitan Oak but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

      We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Oakland is around 40 days in advance, so don’t leave your flight to the last minute.

      Currently, Southwest Airlines offers the cheapest flight tickets to Oakland Metropolitan Oak.

      Travelling from Chicago Midway Airport (MDW) to Oakland Metropolitan Oak Airport (OAK): what you need to know

      • The average duration of a direct flight from Chicago Midway Airport to Oakland Metropolitan Oak Airport is 4 hours 30 minutes.

      • Oakland is two hours behind Chicago and observes the UTC-8 timezone.

      • Choose from seven weekly Chicago Midway Airport to Oakland Metropolitan Oak Airport flights. The 07:30 departure with Southwest Airlines is the earliest you can take. Southwest Airlines operates the latest service of the day at 21:30.

      • Your MDW to OAK flight won't wait if you're late, so be at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead for international travel.

      • Travelling during a peak month like July? Public holidays and other popular seasons can result in longer lines and delays at airport checkpoints. Be extra cautious and arrive up to four hours before an international flight and two hours before a domestic departure.

      • Flying into Oakland (and then exploring more of the United States!) is easy with Southwest Airlines. This popular airline offers direct flights from Chicago Midway Airport to Oakland Metropolitan Oak Airport.

      • The majority of passengers choose to fly with Southwest Airlines on this route.

      • The carrier with the top on-time arrival performance for MDW to OAK flights is Southwest Airlines.

      • We make it simple to book a flight with a stopover. To see your options for tickets from Chicago Midway Airport to Oakland Metropolitan Oak Airport, deselect 'Direct flights only.' Then, pick a flight that has a stop long enough to tour your chosen city. Worthwhile stopovers between MDW and OAK include:

        • Denver International Airport

        • Los Angeles International Airport

        • Harry Reid International Airport

      Handy information about Chicago Midway Airport (MDW)

      • The address for MDW is 5700 South Cicero.

      • 76% of flights that depart Chicago Midway Airport land at their destination on time.

      • Central Chicago to Chicago Midway Airport is approximately 16 kilometres. Depending on traffic, it'll take about 25 minutes to get there if you're catching a taxi, ride-sharing or driving.

      • The trip when using public transport takes about 30 minutes.

      • Get your break off to a relaxed start by staying near MDW. Whether you've booked an early flight from Chicago Midway Airport to Oakland Metropolitan Oak Airport or just don't want to be rushed, these stays are perfect:

      Arriving at Oakland Metropolitan Oak Airport (OAK)

      • Consider booking a hotel close to OAK if you're catching a late Chicago Midway Airport to Oakland Metropolitan Oak Airport flight. Pick one of these accommodation options and avoid the hassle of a long transfer:

      • Say yes to new adventures by picking up a Oakland Metropolitan Oak Airport rental car. Grab your wheels from Europcar, Fox - Rent A Car or Dollar and explore beyond Oakland's usual tourist stops.

      • To lock in the lowest price, reserve your vehicle from Oakland Metropolitan Oak Airport about one week before your trip.

      Getting from Oakland Metropolitan Oak Airport (OAK) to central Oakland

      • You'll find OAK at 1 Airport Drive.

      • Oakland Metropolitan Oak Airport to the centre of Oakland has a drive time of around 20 minutes. It's approximately 11 kilometres away.

      • If you're travelling on public transport, expect a journey time of about 30 minutes.

      When to fly to Oakland Metropolitan Oak Airport (OAK)

      • July is the busiest month for flights from Chicago Midway Airport to Oakland Metropolitan Oak Airport. For smaller crowds, head to Oakland in March.

      • Lock in your flight from Chicago Midway Airport to Oakland Metropolitan Oak Airport for September if you'd like to go to Oakland during its warmest month. You can expect temperatures of between 12ºC (54ºF) and 26ºC (79ºF).

      • If you'd rather travel in cooler conditions, search for a cheap ticket from MDW to OAK in January. Average temperatures are between 4ºC (39ºF) and 17ºC (63ºF) then.

      Explore more of the United States

      • San Jose is just one of the many places in the United States waiting to be discovered once you've seen Oakland. Around 64 kilometres away to the south-east, well-known attractions include Winchester Mystery House, The Tech Interactive and Santa Clara Valley.

      • Around 13 kilometres west of Oakland, San Francisco is another essential stop in the United States. Experience the best of this destination with a visit to Golden Gate Bridge, Painted Ladies - Alamo Square and Alcatraz Island.

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.