Cheap flights from Oakland, California to Chicago from $126
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 11/26. 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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Not ready to book? to track prices.Frontier flights from Oakland, California to Chicago O'Hare Intl Airport
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Alaska Airlines flights from Oakland, California to Chicago O'Hare Intl Airport
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Use the filters below to find and compare flights from Oakland, California to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Thu 11/12
5:55 pm-5:13 am
1 stop9h 18m
Chicago O'Hare Intl
Wed 12/2
6:21 am-11:33 am
1 stop7h 12m
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Sat 11/14
12:41 pm-9:47 pm
1 stop7h 06m
Chicago O'Hare Intl
Wed 12/2
7:25 am-11:54 am
1 stop6h 29m
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Thu 10/29
12:41 pm-10:05 pm
1 stop7h 24m
Chicago O'Hare Intl
Wed 11/4
7:35 am-12:01 pm
1 stop6h 26m
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Thu 11/5
5:55 pm-5:13 am
1 stop9h 18m
Chicago O'Hare Intl
Mon 11/9
5:15 pm-11:53 am
1 stop20h 38m
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Thu 10/29
12:41 pm-10:05 pm
1 stop7h 24m
Chicago O'Hare Intl
Wed 11/4
9:59 am-4:22 pm
2 stops8h 23m
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Thu 11/12
5:55 pm-5:13 am
1 stop9h 18m
Chicago O'Hare Intl
Sat 12/5
6:21 am-11:33 am
1 stop7h 12m
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Thu 11/12
5:55 pm-5:13 am
1 stop9h 18m
Chicago O'Hare Intl
Thu 12/3
6:21 am-11:33 am
1 stop7h 12m
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Tue 11/10
10:00 am-6:59 pm
1 stop6h 59m
Chicago O'Hare Intl
Thu 11/12
7:20 am-2:04 pm
1 stop8h 44m
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Tue 11/3
10:00 am-6:59 pm
1 stop6h 59m
Chicago O'Hare Intl
Wed 11/4
2:07 pm-9:19 pm
1 stop9h 12m
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Thu 11/12
2:44 pm-11:49 pm
1 stop7h 05m
Chicago O'Hare Intl
Tue 11/17
2:15 pm-9:00 pm
1 stop8h 45m
See travel insights to Chicago from
How to get the cheapest flight ticket from Oakland, California to Chicago O'Hare Intl 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 typical price of a round-trip flight between Oakland, California and Chicago O'Hare Intl Airport?
Prices are currently low for flights on this route.
Typical prices usually range from $562 to $607.The lowest price recently found on this route was $248.
What is the cheapest month to fly to Chicago O'Hare Intl Airport?
The month of December is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Oakland, California averaging around $367.
What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?
The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $458. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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 $598.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
Flying to Chicago O'Hare Intl Airport from Oakland, California in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $473 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $529. Of course, these prices can vary depending on the time of year and what airport you fly to.
Can stopping save me money on Oakland, California to Chicago O'Hare Intl Airport flights?
You could potentially save up to 10% on your flight if you consider stops on a Oakland, California to Chicago O'Hare Intl Airport flight.
What is the cheapest airline that flies from Oakland to Chicago O'Hare Intl?
Frontier, Alaska Airlines, and Delta are the most popular carriers operating from Oakland to Chicago O'Hare Intl
What airlines fly to Chicago O'Hare Intl Airport?
United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Oakland, California according to our data. United Airlines is the first choice among our users, with 53% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 7 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
When to book flights from Oakland, California to Chicago O'Hare Intl Airport
Cheap Oakland, California to Chicago O'Hare Intl Airport (OAK to ORD) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Oakland, California to Chicago O'Hare Intl Airport
Frequently asked questions about flying from Oakland, California to Chicago O'Hare Intl Airport
How far is Oakland to Chicago O'Hare Intl by plane?
The distance between Oakland and Chicago O'Hare Intl is about 1830.7 mi. Typically, this will take 6h 38m by plane in normal conditions.
When did momondo last update prices for flights from Oakland Airport to Chicago O'Hare Intl Airport?
Prices for flights from Oakland Airport to Chicago O'Hare Intl Airport refresh daily.
How many operators does momondo search for flights from Oakland Airport to Chicago O'Hare Intl Airport?
The number of operators available for flights from Oakland Airport to Chicago O'Hare Intl Airport is 3 as of October 2026.
How old do you have to be to fly from Oakland Airport to Chicago O'Hare Intl 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 Oakland Airport to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The travel and health documents required for your trip to Chicago O'Hare Intl 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 Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular airline from Oakland, California to Chicago O'Hare Intl Airport?
momondo data reveals that the most frequently booked airline on the route from Oakland, California to Chicago O'Hare Intl Airport is Southwest, representing 51% of all bookings. The subsequent popular airlines are Alaska Airlines at 34% and Delta at 15%.
Best airlines flying from Oakland, California to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Oakland, California to Chicago O'Hare Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $148 | Free Cancellation | Rating 7.8 8,628 reviews | |||
| PriceFrom $272 | Free Cancellation | Rating 7.9 13,015 reviews | |||
| PriceFrom $275 | Free Cancellation | Rating 7.9 4,212 reviews |
Traveling to a place near Chicago?
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Why should I use momondo to find a flight deal from Oakland to Chicago?
It is quick and easy to find Oakland to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Oakland to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Oakland to Chicago flights to just show those with flexible booking policies.
How can momondo help me find flights from Oakland to Chicago?
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 Oakland to Chicago.
I’m not ready to book a flight from Oakland to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Oakland to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.