Cheap flights from Oakland, California to Chicago from $59
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 5/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Spirit Airlines flights from Oakland, California to Chicago
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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
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Oakland, California when booking 23 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $339 when searching 23 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Oakland, California for as low as $185 on momondo.
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.
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 57% 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 (17.72% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (16.54%), Airbus A321neo (9.84%), and Boeing 737-900 Passenger/BBJ3 (winglets) (9.45%).
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 50% of the total bookings. Other popular airlines include Spirit Airlines with 27%, Alaska Airlines with 7%, and Delta with 6%.
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 7,962 reviews | |||
| PriceFrom $138 | Free Cancellation | Rating 8.0 9,968 reviews | |||
| PriceFrom $185 | Free Cancellation | Rating 7.4 8,696 reviews | |||
| PriceFrom $235 | Free Cancellation | Rating 8.0 7,934 reviews | |||
| PriceFrom $263 | Free Cancellation | Rating 8.0 4,294 reviews |
Southwest Flights From Oakland, California to Chicago
Across 10 Southwest flights from Oakland, California to Chicago this week, the average price was $423, with the best Southwest deals starting from $263 round-trip. 4,294 users have rated Southwest on momondo, with an average score of 8.0/10.
Traveling to a place near Chicago?
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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.