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207 € Cheap Flights from Oakland Metropolitan Oak to Chicago Midway

Compare Oakland Metropolitan Oak to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Oakland Metropolitan Oak to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Oakland Metropolitan Oak Airport to Chicago Midway Airport? If you want to travel next month, return fares start from 207 €. Find the lowest prices on one-way and return tickets right here.
Chicago.207 € per passenger.Departing Thu, 29 Oct, returning Mon, 2 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oakland Metropolitan Oak on Thu, 29 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 2 Nov, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 207 €, select.
Chicago.207 € per passenger.Departing Tue, 8 Sep, returning Mon, 28 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oakland Metropolitan Oak on Tue, 8 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 28 Sep, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 207 €, select.
Chicago.207 € per passenger.Departing Thu, 5 Nov, returning Mon, 9 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oakland Metropolitan Oak on Thu, 5 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 9 Nov, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 207 €, select.
Chicago.207 € per passenger.Departing Mon, 10 Aug, returning Wed, 19 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oakland Metropolitan Oak on Mon, 10 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 19 Aug, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 207 €, select.
Chicago.207 € per passenger.Departing Tue, 27 Oct, returning Wed, 28 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oakland Metropolitan Oak on Tue, 27 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 28 Oct, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 207 €, select.
Chicago.208 € per passenger.Departing Tue, 1 Dec, returning Tue, 8 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oakland Metropolitan Oak on Tue, 1 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 8 Dec, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 208 €, select.
Chicago.216 € per passenger.Departing Thu, 26 Nov, returning Thu, 3 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Oakland Metropolitan Oak on Thu, 26 Nov, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 3 Dec, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 216 €, select.
Chicago.221 € per passenger.Departing Sat, 29 Aug, returning Sun, 6 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Oakland Metropolitan Oak on Sat, 29 Aug, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 6 Sep, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 221 €, select.
Chicago.263 € per passenger.Departing Wed, 25 Nov, returning Wed, 2 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oakland Metropolitan Oak on Wed, 25 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 2 Dec, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 263 €, select.
Chicago.272 € per passenger.Departing Thu, 17 Sep, returning Thu, 1 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Oakland Metropolitan Oak on Thu, 17 Sep, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 1 Oct, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 272 €, select.
Chicago.287 € per passenger.Departing Sun, 23 Aug, returning Wed, 2 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oakland Metropolitan Oak on Sun, 23 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 2 Sep, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 287 €, select.
Chicago.352 € per passenger.Departing Mon, 28 Dec, returning Fri, 1 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Oakland Metropolitan Oak on Mon, 28 Dec, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 1 Jan, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 352 €, select.
Chicago.361 € per passenger.Departing Fri, 1 Jan, returning Tue, 5 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Oakland Metropolitan Oak on Fri, 1 Jan, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 5 Jan, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 361 €, select.
Chicago.476 € per passenger.Departing Sat, 25 Jul, returning Tue, 28 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oakland Metropolitan Oak on Sat, 25 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 28 Jul, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 476 €, select.
Chicago.514 € per passenger.Departing Tue, 28 Jul, returning Sat, 1 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oakland Metropolitan Oak on Tue, 28 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 1 Aug, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 514 €, select.

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

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Oakland Metropolitan Oak to Chicago Midway flights are currently cheapest in August.
Jul
from 476 €
Aug
from 207 €
Sep
from 207 €
Oct
from 207 €
Nov
from 207 €
Dec
from 208 €
Jan
from 361 €
Feb
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Mar
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Apr
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May
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Jun
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Direct flights from Oakland Metropolitan Oak to Chicago Midway

Oakland Metropolitan Oak to Chicago Midway: Alternative routes

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

Chicago Midway

14km from central Chicago
ClosestCheapest
from 207 €
Search flights

Chicago O'Hare International

25km from central Chicago
from 228 €
Search flights

Chicago Rockford

127km from central Chicago
from 256 €
Search flights

Oakland to Chicago: Flight information

The things to know before you go.
Cheapest flight found207 €
Cheapest month to flyOctober
Average flight time4 hrs, 3 mins
Most popular airlineSouthwest Airlines
Average flights per week17

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

The best price we found for a return flight from Oakland Metropolitan Oak to Chicago Midway is 207 €. 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 3 minutes is the average flight time from Oakland Metropolitan Oak to Chicago Midway.
Southwest Airlines flies direct from Oakland Metropolitan Oak to Chicago Midway.
As of July 2026, there are 17 flights per week flying from Oakland Metropolitan Oak to Chicago Midway.
The cheapest month to fly from Oakland Metropolitan Oak to Chicago Midway is usually October.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Oakland Metropolitan Oak Airport to Chicago Midway Airport on Tuesday, 27 October 2026.
Yes – the average flight time is 4 hours and 3 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 Chicago Midway 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 Chicago 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 Chicago Midway.

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

  • Take a direct flight from Oakland Metropolitan Oak Airport to Chicago Midway Airport and you'll be travelling for an average of 4 hours 5 minutes.

  • The timezone in Chicago is UTC-6, which is two hours ahead of Oakland.

  • Every week, there are seven Oakland Metropolitan Oak Airport to Chicago Midway Airport flights. If you'd like to be on board as soon as possible, take the 05:05 Southwest Airlines flight. If you're eager to make the most of your time before flying, the last flight is at 18:00 with Southwest Airlines.

  • For a smooth journey, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This will give you enough time to board your OAK to MDW flight.

  • You can expect longer queues in popular months such as July. Arriving up to four hours ahead of an international flight and two hours for domestic departures is a smart move.

  • Southwest Airlines is your gateway to exploring Chicago (and perhaps some other exciting parts of the United States!). Browse the direct flights from Oakland Metropolitan Oak Airport to Chicago Midway Airport offered by this popular carrier.

  • Most travellers choose to travel with Southwest Airlines on this route.

  • Southwest Airlines is the most punctual carrier that offers OAK to MDW flights. An exceptional 84.09% of its departures on this route land as scheduled.

  • If you'd like to split up your journey, simply deselect 'Direct flights only' when searching for your ticket from Oakland Metropolitan Oak Airport to Chicago Midway Airport. Here are the most popular stopovers between OAK and MDW:

    • Denver International Airport

    • Phoenix Sky Harbour Airport

    • Harry Reid International Airport

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

  • The lowest price we've found for a one-way Oakland Metropolitan Oak Airport to Chicago Midway Airport flight is 104 €. A return fare is currently 207 €. Depending on the availability and when you book, these fares may change.

  • Score cheap tickets from OAK to MDW by booking at least one month ahead. According to our research, that's the sweet spot for finding the biggest deals.

  • The cheapest month for flights from Oakland Metropolitan Oak Airport to Chicago Midway Airport is June. Use the 'Whole month' tool to find the lowest prices if you have flexible travel dates.

  • Save time looking for cheap flights from OAK to MDW by setting up a Price Alert. You'll get an email or push notification on the app when a lower fare pops up.

  • Choose your preferred departure and arrival times, airlines and number of stops with the filters. Alternatively, sort your results by 'Cheapest' to see the best deals on flights from Oakland Metropolitan Oak Airport to Chicago Midway Airport.

Handy information about Oakland Metropolitan Oak Airport (OAK)

  • OAK's address is 1 Airport Drive.

  • Oakland Metropolitan Oak Airport has an excellent on-time performance, so flight disruptions are less likely. Departures from OAK touch down on schedule 82% of the time.

  • Oakland Metropolitan Oak Airport is about 11 kilometres from central Oakland. If you're ride-sharing, catching a taxi or driving from the centre, it'll take you 20 minutes or so to arrive, depending on the traffic.

  • Catching public transport? Expect a journey time of around 30 minutes.

  • Have an early flight from Oakland Metropolitan Oak Airport to Chicago Midway Airport? Avoid the hassle of rushing to the terminal (and get some extra shut-eye) by picking one of these stays close to OAK:

Arriving at Chicago Midway Airport (MDW)

  • If you have a late Oakland Metropolitan Oak Airport to Chicago Midway Airport flight, few things beat the convenience of staying near the terminal. Grab your luggage from the carousel and then be showered and sleeping shortly after at one of these accommodation options near MDW:

  • Grab a Chicago Midway Airport rental car and explore Chicago and beyond with your own wheels. Dollar, Hertz and Budget are leading providers you can book with here.

  • To get the lowest price, book your vehicle from Chicago Midway Airport about four weeks ahead.

When to fly to Chicago Midway Airport (MDW)

  • The quietest month for a flight from Oakland Metropolitan Oak Airport to Chicago Midway Airport is December, while July is the busiest. Pick the best time to visit Chicago based on whether you prefer a more fast-paced or easygoing experience.

  • The warmest month in Chicago is July, with the temperature ranging between 16ºC (61ºF) and 28ºC (82ºF). Lock in your flights from Oakland Metropolitan Oak Airport to Chicago Midway Airport in this month if this is the type of weather you like.

  • If you'd rather travel in cooler conditions, look for a cheap ticket from OAK to MDW in January. Average temperatures are between -12ºC (10ºF) and 3ºC (37ºF) then.

Explore more of the United States

  • Chicago is easy to fall in love with, but there are so many other parts of the United States just waiting to be discovered. Around 451 kilometres south-east of Chicago, a trip to Columbus will keep you busy. Start with leading sights like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in the United States. No visit is complete without checking out Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Plan the rest of your trip from Oakland to Chicago

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