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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.
1 adult
0 bags

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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.
Spirit Airlines Logo
10:36 am - 5:25 amOAK-ORD
16h 49m2 stops
Spirit Airlines Logo
11:50 am - 8:14 pmORD-OAK
10h 24m1 stop
$138Spirit Airlines
Find Deal
Thu, May 29 - Tue, Jun 3
Spirit Airlines Logo
9:09 pm - 10:55 amOAK-ORD
11h 46m1 stop
Spirit Airlines Logo
11:50 am - 8:14 pmORD-OAK
10h 24m1 stop
$139Spirit Airlines
Find Deal
Mon, Jun 2 - Mon, Jun 9
Hawaiian Airlines Logo
12:48 pm - 11:59 pmOAK-ORD
9h 11m1 stop
Hawaiian Airlines Logo
6:00 am - 12:08 pmORD-OAK
8h 08m1 stop
$206Hawaiian Airlines
Find Deal
Wed, May 28 - Sat, May 31
Alaska Airlines Logo
12:48 pm - 10:23 pmOAK-ORD
7h 35m1 stop
Alaska Airlines Logo
6:00 am - 1:36 pmORD-OAK
9h 36m1 stop
$216Alaska Airlines
Find Deal
Tue, Jun 3 - Tue, Jun 10
Southwest Logo
9:15 pm - 5:00 amOAK-MDW
5h 45m1 stop
Southwest Logo
7:50 am - 12:05 pmMDW-OAK
6h 15m1 stop
$227Southwest
Find Deal
Mon, Jun 30 - Sat, Jul 12
Southwest Logo
2:05 pm - 11:40 pmOAK-ORD
7h 35m1 stop
Southwest Logo
12:40 pm - 10:45 pmORD-OAK
12h 05m1 stop
$232Southwest
Find Deal
Mon, Jun 30 - Sat, Jul 12
Hawaiian Airlines Logo
7:00 am - 6:55 pmOAK-ORD
9h 55m1 stop
Hawaiian Airlines Logo
6:00 am - 12:08 pmORD-OAK
8h 08m1 stop
$240Hawaiian Airlines
Find Deal
Tue, May 20 - Sat, May 31
Delta Logo
12:30 pm - 10:08 pmOAK-ORD
7h 38m1 stop
Delta Logo
7:20 pm - 11:55 pmORD-OAK
6h 35m1 stop
$257Delta
Find Deal
Wed, Jul 23 - Wed, Jul 30
Delta Logo
4:58 pm - 7:49 amOAK-ORD
12h 51m2 stops
Delta Logo
7:20 pm - 11:55 pmORD-OAK
6h 35m1 stop
$262Delta
Find Deal
Tue, Jul 22 - Tue, Jul 29
Alaska Airlines Logo
12:49 pm - 10:30 pmOAK-ORD
7h 41m1 stop
Alaska Airlines Logo
6:00 am - 12:09 pmORD-OAK
8h 09m1 stop
$276Alaska Airlines
Find Deal
Tue, Jul 22 - Fri, Aug 15

Spirit Airlines flights from Oakland, California to Chicago

Our best Spirit Airlines deals on Oakland, California to Chicago flight tickets
Spirit Airlines
May 29
OAK10:36 amOakland
16h 49m
2 stops
ORD5:25 amChicago O'Hare Intl
Jun 3
ORD11:50 amChicago O'Hare Intl
10h 24m
1 stop
OAK8:14 pmOakland
Spirit Airlines
Jun 2
OAK9:09 pmOakland
11h 46m
1 stop
ORD10:55 amChicago O'Hare Intl
Jun 9
ORD11:50 amChicago O'Hare Intl
10h 24m
1 stop
OAK8:14 pmOakland
Spirit Airlines
May 20
OAK9:09 pmOakland
6h 16m
1 stop
ORD5:25 amChicago O'Hare Intl
May 21
ORD11:50 amChicago O'Hare Intl
10h 24m
1 stop
OAK8:14 pmOakland

Hawaiian Airlines flights from Oakland, California to Chicago

Our best Hawaiian Airlines deals on Oakland, California to Chicago flight tickets
Hawaiian Airlines
May 28
OAK12:48 pmOakland
9h 11m
1 stop
ORD11:59 pmChicago O'Hare Intl
May 31
ORD6:00 amChicago O'Hare Intl
8h 08m
1 stop
OAK12:08 pmOakland
Hawaiian Airlines
May 20
OAK7:00 amOakland
9h 55m
1 stop
ORD6:55 pmChicago O'Hare Intl
May 31
ORD6:00 amChicago O'Hare Intl
8h 08m
1 stop
OAK12:08 pmOakland
Hawaiian Airlines
May 28
OAK12:48 pmOakland
7h 35m
1 stop
ORD10:23 pmChicago O'Hare Intl
Jun 8
ORD6:00 amChicago O'Hare Intl
8h 08m
1 stop
OAK12:08 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 $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.

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

As of April 2025, prices for Oakland, California to Chicago flights are approximately 87% more expensive 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

$59

Fastest flight time

4h 05m

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 $59. The best round-trip flight deal from Oakland, California to Chicago found on momondo in the last 72 hours is $138.
The fastest flight from Oakland, California to Chicago takes 4h 05m
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 $123Free CancellationRating
6.3
7,962 reviews
Search Spirit Airlines flights
Alaska AirlinesPriceFrom $138Free CancellationRating
8.0
9,968 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $185Free CancellationRating
7.4
8,696 reviews
Search United Airlines flights
DeltaPriceFrom $235Free CancellationRating
8.0
7,934 reviews
Search Delta flights
SouthwestPriceFrom $263Free CancellationRating
8.0
4,294 reviews
Search Southwest flights
  • 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?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
Saint John

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.


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1 adult
Mon 5/5
Mon 5/12

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