Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago Midway Airport to San Francisco
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Southwest flights from Chicago Midway Airport to Oakland, California
Our best Southwest deals on Chicago Midway Airport to Oakland, California flight tickets
Delta flights from Chicago Midway Airport to Oakland, California
Our best Delta deals on Chicago Midway Airport to Oakland, California flight tickets
See travel insights to San Francisco from
How to get the cheapest flight ticket from Chicago Midway Airport to Oakland, California
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 Oakland, California?
The month of November is, on average, the cheapest month to fly to Oakland, California from Chicago Midway Airport, with most prices found around $286. If you aren’t able to travel to Oakland, California during the month of November, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $296.
What is the cheapest day to depart on your flight to Oakland, California?
According to our data, Thursday is the cheapest day to fly to Oakland, California from Chicago Midway Airport. The lowest ticket price found for a Thursday departure recently was $326. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Oakland, California for around $532.
What is the cheapest time of day to depart on your flight to Oakland, California?
At noon is the cheapest time of day to fly from Chicago Midway Airport to Oakland, California when you can find flight prices for as low as $337. Flying to Oakland, California at noon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $513.
What is the cheapest Chicago Midway to Oakland flight route?
Fly from Chicago Midway to Oakland for the best Chicago Midway - Oakland flight prices
What is the cheapest airline that flies from Chicago Midway to Oakland?
Southwest and Delta are the most popular carriers operating from Chicago Midway to Oakland
What airlines fly to Oakland, California?
Southwest, Frontier and United Airlines are the top three most popular airlines that fly to Oakland, California from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 57% of people opting to fly with this airline when traveling to Oakland, California. Keep in mind that there are 4 different airlines that fly to Oakland, California on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago Midway Airport to Oakland, California on average per day?
As of April 2025, there are 1 flights per day flying from Chicago Midway Airport to Oakland, California. The most common time of day flights depart is 4:00PM, with 66% of flights taking off in the afternoon.
How many flights depart from Chicago Midway Airport to Oakland, California on average per week?
12 flights are operational weekly from Chicago Midway Airport to Oakland, California as of April 2025. The most popular departure day for this route is Tue, with 33% of flights per week taking off on this day.
When to book flights from Chicago Midway Airport to Oakland, California
Cheap Chicago Midway Airport to Oakland, California (MDW to OAK) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Oakland, California
Best Price Found | $90 |
|---|---|
Fastest flight time | 4h 30m |
Direct flights | Every day |
Airports in Oakland, California | 1 airport |
How far is Chicago Midway to Oakland by plane?
The distance between Chicago Midway and Oakland is about 1839.5 mi. By plane, this route typically takes 4h 30m.
When did momondo last update prices for flights from Chicago Midway Airport to Oakland Airport?
Prices for flights from Chicago Midway Airport to Oakland Airport refresh daily.
How many operators does momondo search for flights from Chicago Midway Airport to Oakland Airport?
As of April 2025, there is 1 operator available to choose from for flights from Chicago Midway Airport to Oakland Airport.
How old do you have to be to fly from Chicago Midway Airport to Oakland Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Oakland Airport.
What documentation or ID do you need to fly to Oakland Airport?
The travel and health documents required for your trip to Oakland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Oakland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago Midway Airport to Oakland, California?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Oakland, California is Boeing 737 MAX 8 (32.17% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (23.78%), Boeing 737-900 Passenger/BBJ3 (winglets) (7.69%), and Airbus A321neo (5.59%).
What is the most popular airline from Chicago Midway Airport to Oakland, California?
Based on momondo bookings for flights between Chicago Midway Airport and Oakland, California, the leading airline is Southwest, making up 100% of the total bookings.
Best airlines flying from Chicago Midway Airport to Oakland, California
Compare and see reviews for airlines that fly from Chicago Midway Airport to Oakland, California with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $247 | Free Cancellation | Rating 8.0 4,280 reviews |
Southwest Flights From Chicago Midway Airport to Oakland, California
Southwest flies from Chicago Midway Airport to Oakland, California around 12 times per week, with 4,280 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago Midway Airport to Oakland, California in the last 72 hours was $247 (round-trip), much lower than the average airfare cost of $365 for Southwest flights on this route.
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Oakland?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Oakland. momondo saves you time and could save you money on your trip.
Can I find flights from Chicago to Oakland with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Chicago to Oakland flights to just show those with flexible booking policies.
How can momondo help me find flights from Chicago to Oakland?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Oakland.
I’m not ready to book a flight from Chicago to Oakland right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Chicago to Oakland flights. All you need is a valid email address and we will do the rest; it is that quick and easy.