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186 € Cheap Flights from Oakland Metropolitan Oak to Chicago

Compare Oakland Metropolitan Oak to Chicago flight deals

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Flight deals from Oakland Metropolitan Oak to Chicago

Looking for a cheap last-minute deal or the best return flight from Oakland Metropolitan Oak Airport to Chicago? 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.186 € per passenger.Departing Mon, 21 Sep, returning Mon, 28 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oakland Metropolitan Oak on Mon, 21 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 186 €, select.
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 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.244 € per passenger.Departing Tue, 25 Aug, returning Wed, 23 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Oakland Metropolitan Oak on Tue, 25 Aug, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 23 Sep, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 244 €, 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.294 € per passenger.Departing Thu, 3 Dec, returning Mon, 7 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from Oakland Metropolitan Oak on Thu, 3 Dec, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 7 Dec, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 294 €, select.
Chicago.346 € per passenger.Departing Fri, 5 Feb, returning Mon, 8 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from Oakland Metropolitan Oak on Fri, 5 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 8 Feb, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 346 €, 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.446 € per passenger.Departing Thu, 30 Jul, returning Mon, 10 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Oakland Metropolitan Oak on Thu, 30 Jul, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 10 Aug, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 446 €, 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.
Chicago.533 € per passenger.Departing Thu, 11 Mar, returning Mon, 15 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Oakland Metropolitan Oak on Thu, 11 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 15 Mar, arriving in Oakland Metropolitan Oak.Price includes taxes and charges.From 533 €, select.

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

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 flights are currently cheapest in September.
Jul
from 476 €
Aug
from 207 €
Sep
from 186 €
Oct
from 207 €
Nov
from 207 €
Dec
from 294 €
Jan
Find prices
Feb
from 346 €
Mar
from 533 €
Apr
Find prices
May
Find prices
Jun
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Direct flights from Oakland Metropolitan Oak to Chicago

Alternative Oakland Metropolitan Oak to Chicago routes

Looking for the cheapest, fastest or easiest route from Oakland Metropolitan Oak to Chicago? You could fly into the following airports instead.

Chicago Midway

14km from central Chicago
ClosestCheapest
from 186 €
Search flights

Chicago O'Hare International

25km from central Chicago
from 228 €
Search flights

Chicago Rockford

127km from central Chicago
from 256 €
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Oakland to Chicago: Flight information

The things to know before you go.
Cheapest flight found186 €
Cheapest month to flySeptember
Average flight time4 hrs, 3 mins
Most popular airlineSouthwest Airlines
Average flights per week34

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

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.
The best price we found for a return flight from Oakland Metropolitan Oak to Chicago is 186 €. 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.
Southwest Airlines flies direct from Oakland Metropolitan Oak to Chicago.
As of July 2026, there are 17 flights per week flying from Oakland Metropolitan Oak to Chicago.
The cheapest month to fly from Oakland Metropolitan Oak to Chicago is usually September.
If you're flying from Oakland Metropolitan Oak Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from 186 €.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Oakland Metropolitan Oak Airport to Chicago on Monday, 21 September 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 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.

In July, the average temperature is usually around 22°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Southwest Airlines offers the cheapest flight tickets to Chicago.

Flying from San Francisco Bay Oakland International Airport (OAK) to Chicago: what you need to know

  • The timezone in Chicago is UTC-6. The city is two hours ahead of Oakland, where San Francisco Bay Oakland International Airport is located.

  • The most popular route is from San Francisco Bay Oakland International Airport (OAK) to Chicago Midway International Airport (MDW). You can select from nine services every week between these two airports. Southwest Airlines offers a 05:05 departure between OAK and MDW.

  • For stress-free travel, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This ensures you have enough time to catch your OAK to Chicago flight.

  • Flying over a peak time such as July? Public holidays and other popular seasons can mean longer queues and delays at security. Be extra cautious and arrive up to four hours before international flights and two hours before domestic departures.

  • Direct San Francisco Bay Oakland International Airport to Chicago tickets are available for booking. Chicago Midway International Airport (MDW) will be where your journey ends.

  • Book your ticket with Southwest Airlines. This popular carrier offers direct flights from San Francisco Bay Oakland International Airport to Chicago.

  • Located around 11 kilometres from the centre of Oakland, OAK can be reached in about 20 minutes by car. The journey on public transport takes roughly 30 minutes.

  • Want an easy start to your holiday? Stay near OAK. Whether you're taking an early flight from San Francisco Bay Oakland International Airport to Chicago or just don't want to be rushed, these hotels have you covered:

  • San Francisco Bay Oakland International Airport maintains a solid on-time performance, reducing the likelihood of delays. Departures from OAK make it to their destination as scheduled 82% of the time.

  • OAK is located at 1 Airport Drive.

How to find the cheapest flights from San Francisco Bay Oakland International Airport (OAK) to Chicago

  • The best price we've seen for a one-way San Francisco Bay Oakland International Airport to Chicago flight is 75 €. The cheapest price for a return flight is 186 €. Bear in mind fares may change due to demand at the time of booking.

  • Get cheap flights from OAK to Chicago by booking one month ahead. Based on our research, that's the best time for finding a bargain.

  • Schedule your trip for June. That's the best month for landing a bargain on San Francisco Bay Oakland International Airport to Chicago tickets. If you're flexible with your dates, use the 'Whole month' tool to access the lowest price across every month.

  • Stay on top of deals for cheap flights from OAK to Chicago by setting up a Price Alert. You'll receive an email or push notification on the app when a lower fare becomes available.

  • Pick your ideal arrival and departure times, airlines and number of stops with our filters. Then, sort the results for your flight from San Francisco Bay Oakland International Airport to Chicago by 'Fastest,' 'Best' or 'Cheapest.'

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) is around 27 kilometres from central Chicago. If you're getting a taxi or a ride-share, the drive takes about 30 minutes.

  • If you're travelling on public transport, expect a journey time of around 45 minutes.

  • If you're arriving on a late flight from San Francisco Bay Oakland International Airport to Chicago, nothing beats the convenience of staying close to the terminal. Pick up your bags from the carousel and then be showered and relaxing soon after at one of these accommodation options near ORD:

  • For the lowest price, reserve your vehicle from Chicago O'Hare International Airport about four weeks ahead of your flight from OAK to Chicago.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Once your flight from San Francisco Bay Oakland International Airport to Chicago has landed, you can make your way to the city centre in about 25 minutes by car. Central Chicago is roughly 16 kilometres from Chicago Midway International Airport (MDW).

  • If you choose to travel on public transport, you'll reach the centre in 30 minutes or so.

  • Following your OAK to Chicago flight, settle in at a hotel close to MDW. These are some great accommodation options that'll help you switch to relaxation mode:

  • Secure your first choice, not your last resort. Booking your ride from MDW four weeks in advance often means better prices and a wider choice of vehicles.

  • Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is around 145 kilometres from the centre of Chicago. It takes about 1 hour 40 minutes to reach the city centre by ride-share or taxi after your flight from San Francisco Bay Oakland International Airport to Chicago.

  • If you use public transport, the journey time is about 2 hours.

  • If you don't want to make your way into the centre, choose a hotel near RFD. Get settled at one of these options after your OAK to Chicago flight:

  • If you're hoping for a specific kind of vehicle, booking early increases your chances of getting your first choice. Reserve your ride from RFD a few weeks ahead of your flight from San Francisco Bay Oakland International Airport to Chicago.

  • Chicago Rockford International Airport's street address is 2 Airport Cir.

Best time to go to Chicago

  • It's time to choose your trip dates for your flight from San Francisco Bay Oakland International Airport to Chicago. July is the busiest month to visit Chicago. If you like a more relaxed vibe, go in January.

  • When booking your San Francisco Bay Oakland International Airport to Chicago plane ticket, think about the type of weather you enjoy. July is the warmest month in Chicago, with temperatures ranging from 16ºC (61ºF) to 28ºC (82ºF).

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for a cheap ticket from OAK to Chicago around that time if you want to travel in cooler conditions.

More about Chicago

Explore more of the United States

  • Columbus is just one of the many cities in the United States waiting to be discovered after you've seen Chicago. Around 451 kilometres away to the southeast, top sights here include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Indianapolis is another essential stop in the United States and is around 257 kilometres southeast of Chicago. No trip is complete without experiencing 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.