Cheap flights from Oakland, California to Chicago from $77
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Oakland, California to Chicago departing on 5/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
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 Oakland, California to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Spirit Airlines flights from Oakland, California to Chicago
Our best Spirit Airlines deals on Oakland, California to Chicago flight tickets
Alaska Airlines flights from Oakland, California to Chicago
Our best Alaska Airlines deals on Oakland, California to Chicago flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from Oakland, California to Chicago
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 typical price of a round-trip flight between Oakland, California and Chicago?
What is the cheapest month to fly to Chicago?
The month of April is, on average, the cheapest month to fly to Chicago from Oakland, California, with most prices found around $96. If you’re not able to fly to Chicago in April, then August is your next best option. Flight prices from Oakland, California to Chicago during August average around $235.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $414. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Oakland, California to Chicago for around $564.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Oakland, California to Chicago during this time can be as low as $374. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $543.
What is the cheapest Oakland to Chicago flight route?
Fly from Oakland to Chicago Midway for the best Oakland - Chicago flight prices
What cabin class options are available on Oakland to Chicago flights?
There are 1 cabin classes available to choose from on Oakland to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
How have Oakland, California to Chicago flight prices changed over time?
As of April 2025, prices for Oakland, California to Chicago flights are approximately 79% more expensive when compared to flights at the same time last year.
What is the cheapest airline that flies from Oakland to Chicago?
Spirit Airlines, Southwest, and Alaska Airlines are the most popular carriers operating from Oakland to Chicago
What airlines fly to Chicago?
United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago from Oakland, California according to our data. United Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 8 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Oakland, California to Chicago on average per day?
1 flights are operational daily from Oakland, California to Chicago as of April 2025. The most popular departure time for this route is 5:00AM, with 60% of flights per day taking off at noon.
How many flights depart from Oakland, California to Chicago on average per week?
As of April 2025, 10 flights take off from Oakland, California and land in Chicago each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.
When to book flights from Oakland, California to Chicago
Cheap Oakland, California to Chicago (OAK to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Oakland, California to Chicago
How far is Oakland to Chicago by plane?
The distance between Oakland and Chicago is about 1845.3 mi. Typically, this will take 4h 05m by plane in normal conditions.
When did momondo last update prices for flights from Oakland Airport to Chicago?
Prices for flights from Oakland Airport to Chicago are updated daily.
How many operators does momondo search for flights from Oakland Airport to Chicago?
As of April 2025, there are 5 operators available to choose from for flights from Oakland Airport to Chicago.
How old do you have to be to fly from Oakland Airport to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Oakland Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago 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 Chicago. 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 Oakland, California to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Oakland, California to Chicago is Boeing 737 MAX 8 (18.72% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (17.24%), Boeing 737-900 Passenger/BBJ3 (winglets) (8.37%), and Airbus A321neo (7.88%).
What is the most popular airline from Oakland, California to Chicago?
Based on momondo bookings for flights between Oakland, California and Chicago, the leading airline is Southwest, making up 44% of the total bookings. Other popular airlines include Spirit Airlines with 27%, Frontier with 11%, and Alaska Airlines with 7%.
Best airlines flying from Oakland, California to Chicago
Compare and see reviews for airlines that fly from Oakland, California to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $123 | Free Cancellation | Rating 6.3 7,926 reviews | |||
| PriceFrom $138 | Free Cancellation | Rating 8.0 9,882 reviews | |||
| PriceFrom $185 | Free Cancellation | Rating 7.4 8,667 reviews | |||
| PriceFrom $235 | Free Cancellation | Rating 8.0 7,917 reviews | |||
| PriceFrom $263 | Free Cancellation | Rating 8.0 4,280 reviews |
Southwest Flights From Oakland, California to Chicago
Across 10 Southwest flights from Oakland, California to Chicago this week, the average price was $425, with the best Southwest deals starting from $263 round-trip. 4,280 users have rated Southwest on momondo, with an average score of 8.0/10.
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?
momondo does allow users to show only those flights to Chicago from Oakland which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Oakland to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Oakland.
I’m not ready to book a flight from Oakland to Chicago right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Oakland to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.