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Not ready to book? to track prices.Find the cheapest flights from Oakland, California to Chicago
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Delta flights from Oakland, California to Chicago Midway Airport
Our best Delta deals on Oakland, California to Chicago Midway Airport flight tickets
Southwest flights from Oakland, California to Chicago Midway Airport
Our best Southwest deals on Oakland, California to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from Oakland, California to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago Midway Airport?
The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from Oakland, California, with most prices found around $308. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Oakland, California during the month July is also very affordable. Most momondo users find prices during this month for around $363.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Oakland, California. The lowest ticket price found for a Saturday departure recently was $321. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Oakland, California because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $508.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Oakland, California in the evening is the least expensive time of day to depart. momondo users have found prices as low as $284 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $535. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Oakland to Chicago Midway flight route?
Fly from Oakland to Chicago Midway for the best Oakland - Chicago Midway flight prices
What cabin class options are available on Oakland to Chicago Midway flights?
There are 1 cabin classes available to choose from on Oakland to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Oakland, California to Chicago Midway Airport flights?
No. A direct flight is the cheapest option for a flight between Oakland, California to Chicago Midway Airport.
What is the cheapest airline that flies from Oakland to Chicago Midway?
Southwest and Delta are the most popular carriers operating from Oakland to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Frontier and United Airlines are the top three most popular airlines that fly to Chicago Midway Airport from Oakland, California according to our data. Southwest is the first choice among our users, with 64% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 6 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Oakland, California to Chicago Midway Airport on average per day?
The number of flights available between Oakland, California and Chicago Midway Airport is 1 per day as of June 2025. The most frequent departure time is 12:00PM, with 46% of daily flights leaving in the afternoon.
How many flights depart from Oakland, California to Chicago Midway Airport on average per week?
As of June 2025, there are 7 flights per week flying from Oakland, California to Chicago Midway Airport. The most common day of the week flights depart is Tue, with 29% of flights taking off on this day.
When to book flights from Oakland, California to Chicago Midway Airport
Cheap Oakland, California to Chicago Midway Airport (OAK to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Oakland, California to Chicago Midway Airport
How far is Oakland to Chicago Midway by plane?
There are 1839.5 mi between Oakland and Chicago Midway. In terms of flight time, this usually takes a little over 4h 05m.
When did momondo last update prices for flights from Oakland Airport to Chicago Midway Airport?
Prices for flights from Oakland Airport to Chicago Midway Airport are updated daily.
How many operators does momondo search for flights from Oakland Airport to Chicago Midway Airport?
There is 1 operator available for flights from Oakland Airport to Chicago Midway Airport as of June 2025.
How old do you have to be to fly from Oakland Airport to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Oakland Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Oakland, California to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Oakland, California to Chicago Midway Airport is Boeing 737 MAX 8, representing 23.08% of all bookings. The subsequent popular models are Airbus A321neo at 12.50%, Boeing 737-900 Passenger/BBJ3 (winglets) at 11.54%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 10.10%.
What is the most popular airline from Oakland, California to Chicago Midway Airport?
Based on momondo bookings for flights between Oakland, California and Chicago Midway Airport, the leading airline is Southwest, making up 100% of the total bookings.
Best airlines flying from Oakland, California to Chicago Midway Airport
Compare and see reviews for airlines that fly from Oakland, California to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $276 | Free Cancellation | Rating 8.0 4,280 reviews |
Southwest Flights From Oakland, California to Chicago Midway Airport
Southwest flight deals from Oakland, California to Chicago Midway Airport start from $276 round-trip. Over the 7 Southwest flights for this route in a normal week, average airfare is usually $417 round-trip - but some users have found much cheaper deals with momondo.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Oakland to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Oakland.
Can I find flights from Oakland to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Oakland on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Oakland to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Oakland. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Oakland to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Oakland are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.