Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Oakland, California to Chicago from $61

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 1/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
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

These are some of the best round-trip flight deals from Oakland, California to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Oakland, California to Chicago.

Cheap last minute flights

Planning a quick getaway from Oakland, California to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Oakland, California to Chicago

Find recent round-trip train or bus tickets from Oakland, California to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
7:02 pm - 5:31 amOAK-ORD
8h 29m1 stop
1:39 pm - 7:25 pmORD-OAK
7h 46m1 stop
$104Spirit Airlines
Find Deal
Wed, Jan 22 - Tue, Jan 28
7:02 pm - 5:31 amOAK-ORD
8h 29m1 stop
1:39 pm - 9:35 pmORD-OAK
9h 56m1 stop
$108Spirit Airlines
Find Deal
Sat, Jan 18 - Tue, Jan 21
6:19 pm - 5:31 amOAK-ORD
9h 12m1 stop
7:45 am - 1:41 pmORD-OAK
7h 56m1 stop
Sun, Jan 26 - Sun, Feb 2
11:05 am - 5:10 pmOAK-MDW
4h 05mnonstop
5:10 pm - 8:00 pmMDW-OAK
4h 50mnonstop
$228Southwest
Find Deal
Tue, Feb 11 - Sat, Feb 15
11:25 am - 5:30 pmOAK-MDW
4h 05mnonstop
9:40 am - 12:35 pmMDW-OAK
4h 55mnonstop
$253Southwest
Find Deal
Fri, Feb 7 - Sun, Feb 9
6:00 am - 2:12 pmOAK-ORD
6h 12m1 stop
7:15 am - 12:30 pmORD-OAK
7h 15m1 stop
$256Delta
Find Deal
Tue, Feb 4 - Sat, Feb 8
6:00 am - 4:13 pmOAK-ORD
8h 13m2 stops
7:20 pm - 11:56 pmORD-OAK
6h 36m1 stop
$261Delta
Find Deal
Thu, Jan 23 - Thu, Jan 30
10:41 am - 1:07 pmOAK-ORD
24h 26m1 stop
7:45 am - 8:49 amORD-OAK
27h 04m2 stops
$264Alaska Airlines
Find Deal
Wed, Jan 22 - Tue, Jan 28
4:43 pm - 6:05 amOAK-ORD
11h 22m1 stop
2:07 pm - 11:44 pmORD-OAK
11h 37m2 stops
$280Alaska Airlines
Find Deal
Tue, Apr 22 - Tue, May 6
5:10 am - 8:52 pmOAK-RFD
13h 42m1 stop
9:42 pm - 3:19 pmRFD-OAK
19h 37m2 stops
Thu, Feb 13 - Sun, Feb 16
7:02 pm - 5:31 amOAK-ORD
8h 29m1 stop
$61Spirit Airlines
Find Deal
Tue, Jan 14
12:40 pm - 9:44 pmOAK-ORD
7h 04m1 stop
$65Spirit Airlines
Find Deal
Sat, Feb 15
11:05 am - 5:10 pmOAK-MDW
4h 05mnonstop
$99Southwest
Find Deal
Thu, Jan 30
6:32 am - 5:59 pmOAK-ORD
9h 27m1 stop
$108Alaska Airlines
Find Deal
Thu, Jan 23
6:10 am - 12:15 pmOAK-MDW
4h 05mnonstop
$109Southwest
Find Deal
Fri, Feb 21
9:46 am - 1:04 pmOAK-ORD
25h 18m1 stop
$124Alaska Airlines
Find Deal
Thu, Mar 6
6:00 am - 2:12 pmOAK-ORD
6h 12m1 stop
$128Delta
Find Deal
Tue, Feb 4
5:00 pm - 10:12 amOAK-MDW
15h 12m2 stops
$133Delta
Find Deal
Thu, Feb 27
7:02 pm - 11:54 amOAK-RFD
14h 52m1 stop
Sat, Jan 25
2:02 pm - 10:09 amOAK-MDW
18h 07m2 stops
Thu, May 8
6:36 pm - 5:30 amOAK-ORD
8h 54m1 stop
9:54 pm - 9:43 amORD-OAK
13h 49m1 stop
$336Spirit Airlines
Find Deal
Fri, Jan 3 - Tue, Jan 7
2:04 pm - 5:30 amOAK-ORD
37h 26m2 stops
1:39 pm - 7:25 pmORD-OAK
7h 46m1 stop
$421Spirit Airlines
Find Deal
Thu, Jan 2 - Tue, Jan 28
12:49 pm - 9:39 pmOAK-ORD
6h 50m1 stop
5:00 pm - 11:56 pmORD-OAK
8h 56m1 stop
$442Delta
Find Deal
Thu, Jan 2 - Tue, Jan 28
2:04 pm - 5:30 amOAK-ORD
37h 26m2 stops
1:39 pm - 10:42 amORD-OAK
23h 03m2 stops
$444Spirit Airlines
Find Deal
Thu, Jan 2 - Tue, Jan 28
7:32 pm - 5:30 amOAK-ORD
7h 58m1 stop
10:47 pm - 6:47 amORD-OAK
10h 00m1 stop
Thu, Jan 2 - Thu, Jan 9
5:30 am - 12:33 amOAK-ORD
17h 03m2 stops
4:27 pm - 6:47 amORD-OAK
16h 20m2 stops
$450Spirit Airlines
Find Deal
Thu, Jan 2 - Thu, Jan 9
5:30 am - 5:44 pmOAK-MDW
10h 14m2 stops
1:26 pm - 11:56 pmMDW-OAK
12h 30m2 stops
$452Delta
Find Deal
Thu, Jan 2 - Tue, Jan 28
10:50 am - 4:55 pmOAK-MDW
4h 05mnonstop
9:50 pm - 12:35 amMDW-OAK
4h 45mnonstop
$610Southwest
Find Deal
Tue, Dec 31 - Sat, Jan 4
3:30 pm - 11:25 pmOAK-MDW
5h 55m1 stop
9:50 pm - 12:35 amMDW-OAK
4h 45mnonstop
$615Southwest
Find Deal
Tue, Dec 31 - Sat, Jan 4
7:32 pm - 5:30 amOAK-ORD
7h 58m1 stop
2:01 pm - 11:59 pmORD-OAK
11h 58m2 stops
$921Alaska Airlines
Find Deal
Wed, Jan 1 - Fri, Jan 3
11:05 am - 5:10 pmOAK-MDW
4h 05mnonstop
5:10 pm - 8:00 pmMDW-OAK
4h 50mnonstop
$228Southwest
Find Deal
Tue, Feb 11 - Sat, Feb 15
11:25 am - 5:30 pmOAK-MDW
4h 05mnonstop
9:40 am - 12:35 pmMDW-OAK
4h 55mnonstop
$253Southwest
Find Deal
Fri, Feb 7 - Sun, Feb 9
6:10 am - 12:15 pmOAK-MDW
4h 05mnonstop
6:20 pm - 9:15 pmMDW-OAK
4h 55mnonstop
$308Southwest
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 5:25 pmOAK-MDW
4h 05mnonstop
4:25 pm - 7:15 pmMDW-OAK
4h 50mnonstop
$328Southwest
Find Deal
Sun, Jan 26 - Sun, Feb 2
7:40 am - 1:45 pmOAK-MDW
4h 05mnonstop
3:05 pm - 5:55 pmMDW-OAK
4h 50mnonstop
$348Southwest
Find Deal
Sat, Jan 18 - Sat, Feb 1
6:35 am - 12:40 pmOAK-MDW
4h 05mnonstop
5:35 pm - 8:15 pmMDW-OAK
4h 40mnonstop
$428Southwest
Find Deal
Sat, Mar 8 - Sat, Mar 15
11:25 am - 5:30 pmOAK-MDW
4h 05mnonstop
4:25 pm - 7:15 pmMDW-OAK
4h 50mnonstop
$441Southwest
Find Deal
Thu, Jan 16 - Mon, Jan 20
11:05 am - 5:10 pmOAK-MDW
4h 05mnonstop
4:25 pm - 7:15 pmMDW-OAK
4h 50mnonstop
$592Southwest
Find Deal
Thu, Jan 9 - Sun, Jan 12

Spirit Airlines flights from Oakland, California to Chicago

Our best Spirit Airlines deals on Oakland, California to Chicago flight tickets
Spirit Airlines
Jan 22
OAK7:02 pmOakland
8h 29m
1 stop
ORD5:31 amChicago O'Hare Intl
Jan 28
ORD1:39 pmChicago O'Hare Intl
7h 46m
1 stop
OAK7:25 pmOakland
Spirit Airlines
Jan 18
OAK7:02 pmOakland
8h 29m
1 stop
ORD5:31 amChicago O'Hare Intl
Jan 21
ORD1:39 pmChicago O'Hare Intl
9h 56m
1 stop
OAK9:35 pmOakland
Spirit Airlines
Jan 16
OAK6:19 pmOakland
9h 12m
1 stop
ORD5:31 amChicago O'Hare Intl
Jan 21
ORD1:39 pmChicago O'Hare Intl
9h 56m
1 stop
OAK9:35 pmOakland

Delta flights from Oakland, California to Chicago

Our best Delta deals on Oakland, California to Chicago flight tickets
Delta
Feb 4
OAK6:00 amOakland
6h 12m
1 stop
ORD2:12 pmChicago O'Hare Intl
Feb 8
ORD7:15 amChicago O'Hare Intl
7h 15m
1 stop
OAK12:30 pmOakland
Delta
Jan 23
OAK6:00 amOakland
8h 13m
2 stops
ORD4:13 pmChicago O'Hare Intl
Jan 30
ORD7:20 pmChicago O'Hare Intl
6h 36m
1 stop
OAK11:56 pmOakland
Delta
Jan 24
OAK6:00 amOakland
9h 29m
2 stops
ORD5:29 pmChicago O'Hare Intl
Feb 1
ORD2:15 pmChicago O'Hare Intl
10h 39m
2 stops
OAK10:54 pmOakland

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 $297. If you’re not able to fly to Chicago in April, then February is your next best option. Flight prices from Oakland, California to Chicago during February average around $300.

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 $306. 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 $391.

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 $280. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $428.

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.

Can stopping save me money on Oakland, California to Chicago flights?

You could potentially save up to 38% on your flight if you consider stops on a Oakland, California to Chicago flight.

How have Oakland, California to Chicago flight prices changed over time?

As of December 2024, prices for Oakland, California to Chicago flights are approximately 5% cheaper when compared to flights at the same time last year.

When to book flights from Oakland, California to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Oakland, California to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

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

Best Price Found

$61

Fastest flight time

4h 00m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Oakland, California in the past 72 hours is $61. The best round-trip flight deal from Oakland, California to Chicago found on momondo in the last 72 hours is $104.
The fastest flight from Oakland, California to Chicago takes 4h 00m
Direct flights go from Oakland, California to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • 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?

  • 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?

  • What is the most popular airline from Oakland, California to Chicago?


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
Spirit AirlinesPriceFrom $133Free CancellationRating
6.3
8,100 reviews
Search Spirit Airlines flights
Alaska AirlinesPriceFrom $138Free CancellationRating
8.0
9,583 reviews
Search Alaska Airlines flights
DeltaPriceFrom $236Free CancellationRating
8.0
8,546 reviews
Search Delta flights
SouthwestPriceFrom $263Free CancellationRating
8.1
4,722 reviews
Search Southwest flights
  • Southwest Flights From Oakland, California to Chicago

    Across 16 Southwest flights from Oakland, California to Chicago this week, the average price was $405, with the best Southwest deals starting from $263 round-trip. 4,722 users have rated Southwest on momondo, with an average score of 8.1/10.


Why 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.


An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Fri 1/3
Fri 1/10
Email me momondo's favorite deals

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago