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Cheap Flights from Chicago Midway to Oakland Metropolitan Oak

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

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Flight deals from Chicago Midway to Oakland Metropolitan Oak

Looking for a cheap last-minute deal or the best return flight from Chicago Midway to Oakland Metropolitan Oak? Find the lowest prices on one-way and return tickets right here.
Oakland.215 € per passenger.Departing Fri, 4 Jul, returning Tue, 15 Jul.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 4 Jul, arriving in Oakland Metropolitan Oak.Inbound indirect flight with Southwest Airlines, departs from Oakland Metropolitan Oak on Tue, 15 Jul, arriving in Chicago Midway.Price includes taxes and charges.From 215 €, select.
Oakland.228 € per passenger.Departing Fri, 5 Sep, returning Mon, 8 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 5 Sep, arriving in Oakland Metropolitan Oak.Inbound direct flight with Southwest Airlines departs from Oakland Metropolitan Oak on Mon, 8 Sep, arriving in Chicago Midway.Price includes taxes and charges.From 228 €, select.
Oakland.249 € per passenger.Departing Fri, 15 Aug, returning Mon, 18 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 15 Aug, arriving in Oakland Metropolitan Oak.Inbound indirect flight with Southwest Airlines, departs from Oakland Metropolitan Oak on Mon, 18 Aug, arriving in Chicago Midway.Price includes taxes and charges.From 249 €, select.
Oakland.263 € per passenger.Departing Wed, 3 Dec, returning Mon, 8 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 3 Dec, arriving in Oakland Metropolitan Oak.Inbound indirect flight with Southwest Airlines, departs from Oakland Metropolitan Oak on Mon, 8 Dec, arriving in Chicago Midway.Price includes taxes and charges.From 263 €, select.
Oakland.291 € per passenger.Departing Mon, 30 Jun, returning Sun, 6 Jul.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 30 Jun, arriving in Oakland Metropolitan Oak.Inbound indirect flight with Southwest Airlines, departs from Oakland Metropolitan Oak on Sun, 6 Jul, arriving in Chicago Midway.Price includes taxes and charges.From 291 €, select.
Oakland.300 € per passenger.Departing Sat, 28 Jun, returning Mon, 30 Jun.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 28 Jun, arriving in Oakland Metropolitan Oak.Inbound indirect flight with Southwest Airlines, departs from Oakland Metropolitan Oak on Mon, 30 Jun, arriving in Chicago Midway.Price includes taxes and charges.From 300 €, select.
Oakland.341 € per passenger.Departing Thu, 24 Jul, returning Fri, 1 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 24 Jul, arriving in Oakland Metropolitan Oak.Inbound indirect flight with Southwest Airlines, departs from Oakland Metropolitan Oak on Fri, 1 Aug, arriving in Chicago Midway.Price includes taxes and charges.From 341 €, select.
Oakland.422 € per passenger.Departing Wed, 23 Jul, returning Sun, 27 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 23 Jul, arriving in Oakland Metropolitan Oak.Inbound direct flight with Southwest Airlines departs from Oakland Metropolitan Oak on Sun, 27 Jul, arriving in Chicago Midway.Price includes taxes and charges.From 422 €, 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 July.
Jun
from 300 €
Jul
from 215 €
Aug
from 249 €
Sep
from 228 €
Oct
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Nov
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Dec
from 263 €
Jan
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Feb
from 758 €
Mar
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Apr
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May
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Direct flights from Chicago Midway to Oakland Metropolitan Oak

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.

Chicago to Oakland: Flight information

The things to know before you go.
Cheapest flight found215 €
Cheapest month to flyJuly
Average flight time4 hrs, 37 mins
Most popular airlineSouthwest Airlines
Average flights per week9

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 215 €. 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 37 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 June 2025, there are 9 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 June 2025.
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 Friday, 4 July 2025.
Yes – the average flight time is 4 hours and 37 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 International Airport (MDW) to Metropolitan Oakland International Airport (OAK): what you need to know

  • Jump on a direct flight from Chicago Midway International Airport to Metropolitan Oakland International Airport and you'll be travelling for an average of 4 hours 35 minutes.

  • Oakland is two hours behind Chicago and observes the UTC-7 timezone.

  • Take your pick of nine weekly Chicago Midway International Airport to Metropolitan Oakland International Airport flights. The 05:35 departure with Southwest Airlines is the earliest flight you can take. Southwest Airlines operates the latest service of the day at 22:40.

  • For a stress-free journey, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This ensures you have enough time to board your MDW to OAK flight.

  • During popular months like July, it's best to get to the airport well in advance. Arrive two hours before domestic departures and four hours ahead of an international flight whenever you're travelling during peak periods in general.

  • Southwest Airlines has direct flights from Chicago Midway International Airport to Metropolitan Oakland International Airport. Book with this popular carrier, then get ready to check out the sights in Oakland — and maybe even more of United States if you have time.

  • The airline most travellers fly with on this route is Southwest Airlines.

  • Southwest Airlines is the most punctual carrier offering MDW to OAK flights, with 65.67% of its services landing on time.

  • Think about adding a stopover when booking your ticket from Chicago Midway International Airport to Metropolitan Oakland International Airport. Just uncheck 'Direct flights only' to break up your journey, or even explore someplace new along the way. Here are some options between MDW and OAK:

    • Denver International Airport

    • Harry Reid Airport (formerly McCarran Airport)

    • Los Angeles International Airport

How to find the cheapest flights from Chicago Midway International Airport (MDW) to Metropolitan Oakland International Airport (OAK)

  • The cheapest price we've seen for a one-way Chicago Midway International Airport to Metropolitan Oakland International Airport flight is 86 €. A round-trip fare right now is 215 €. Depending on the availability and when you book, these fares may change.

  • Book six months before flying. After crunching the numbers on our calendar, this is how far you should book ahead to find cheap tickets from MDW to OAK.

  • Schedule your trip for May. That's the cheapest month for flights from Chicago Midway International Airport to Metropolitan Oakland International Airport. If you're flexible with your dates, try out the 'Whole month' tool to see the cheapest airfare across every month.

  • You won't have to check every day to find out if fares have gone down when you create a Price Alert. We'll send you an update the moment there's a new deal on cheap flights from MDW to OAK.

  • Tailor your flights with filters. Choose your preferred departure and arrival times, airlines and total journey duration. You can also sort your results by 'Fastest,' 'Best' or 'Cheapest' flights from Chicago Midway International Airport to Metropolitan Oakland International Airport.

Handy information about Chicago Midway International Airport (MDW)

  • MDW's address is 5700 South Cicero.

  • Of all flights departing from Chicago Midway International Airport, 77.88% land on schedule at their destination.

  • Central Chicago to Chicago Midway International Airport is around 19 kilometres. Depending on traffic, it'll take you about 20 minutes to get there if you're driving, ride-sharing or catching a cab.

  • Expect a journey time of roughly 45 minutes on public transport.

  • Searching for a handy hotel near MDW? If you've booked an early flight from Chicago Midway International Airport to Metropolitan Oakland International Airport, these stays will have you moments from your departure lounge:

Arriving at Metropolitan Oakland International Airport (OAK)

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

  • OAK is located at 1 Airport Drive.

  • Metropolitan Oakland International Airport to the centre of Oakland has a drive time of around 15 minutes. It's approximately 16 kilometres away.

  • When travelling on public transport, expect a journey time of about 40 minutes.

When to fly to Metropolitan Oakland International Airport (OAK)

  • It's time to plan your travel dates for your flight from Chicago Midway International Airport to Metropolitan Oakland International Airport. July is the busiest month to head to Oakland. If you're after a more laid-back vibe, go in May.

  • Book your flight from Chicago Midway International Airport to Metropolitan Oakland International Airport for September if you'd like to explore Oakland during its warmest month. Expect temperatures of between 12ºC (54ºF) and 26ºC (79ºF).

  • For cooler conditions, search for a cheap ticket from MDW to OAK in January. Temperatures average between 4ºC (39ºF) and 17ºC (63ºF) then.

Explore more of United States

  • San Jose is just one of the many cities in United States waiting to be explored after you've seen Oakland. Around 64 kilometres away to the south-east, check out popular attractions including Winchester Mystery House, Rosicrucian Egyptian Museum and San Jose Museum of Art.

  • Around 13 kilometres west of Oakland, San Francisco is another favourite stop in United States. Experience this destination's highlights firsthand at Golden Gate Bridge, Alcatraz Island and Lombard Street.

Plan the rest of your trip from Chicago to Oakland

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.