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Cheap flights from Oakland, California to Chicago from $109

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 2/21. 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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Find the cheapest flights from Oakland, California to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
8:50 pm - 11:25 pm
MDW
-
OAK
4h 35mnonstop
$217Southwest
Sat, Apr 18 - Wed, Apr 22
Southwest Logo
6:30 am - 12:35 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
2:10 pm - 7:50 pm
MDW
-
OAK
7h 40m
1 stop
$227Southwest
Tue, Feb 17 - Tue, Feb 24
Southwest Logo
6:30 am - 12:35 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
8:10 am - 2:55 pm
MDW
-
OAK
8h 45m
2 stops
$233Southwest
Tue, Feb 17 - Tue, Feb 24
Southwest Logo
1:15 pm - 9:20 pm
OAK
-
MDW
6h 05m
1 stop
Southwest Logo
4:30 pm - 8:45 pm
MDW
-
OAK
6h 15m
1 stop
$237Southwest
Sat, Apr 18 - Wed, Apr 22
Southwest Logo
4:15 pm - 12:25 am
OAK
-
MDW
6h 10m
1 stop
Southwest Logo
8:10 am - 2:55 pm
MDW
-
OAK
8h 45m
2 stops
$242Southwest
Tue, Feb 17 - Tue, Feb 24
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
8:50 pm - 11:25 pm
MDW
-
OAK
4h 35mnonstop
$249Southwest
Tue, May 5 - Wed, May 13
Southwest Logo
6:30 am - 12:35 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
9:30 pm - 12:10 am
MDW
-
OAK
4h 40mnonstop
$250Southwest
Tue, Feb 17 - Thu, Mar 5
Southwest Logo
6:30 am - 12:35 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
5:40 pm - 10:20 pm
MDW
-
OAK
6h 40m
1 stop
$256Southwest
Tue, Feb 17 - Thu, Mar 5
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
6:45 am - 12:10 pm
MDW
-
OAK
7h 25m
1 stop
$259Southwest
Sat, May 2 - Sat, May 16
Southwest Logo
6:30 am - 12:35 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
7:45 am - 12:45 pm
MDW
-
OAK
7h 00m
1 stop
$260Southwest
Tue, Feb 17 - Fri, Feb 20

Delta flights from Oakland, California to Chicago Midway Airport

Our best Delta deals on Oakland, California to Chicago Midway Airport flight tickets
Delta
Feb 18
OAK5:55 amOakland
9h 42m
2 stops
MDW5:37 pmChicago Midway
Feb 25
MDW1:26 pmChicago Midway
12h 25m
2 stops
OAK11:51 pmOakland
$351
Delta
Jan 27
OAK5:55 amOakland
10h 00m
2 stops
MDW5:55 pmChicago Midway
Feb 2
MDW1:51 pmChicago Midway
12h 02m
2 stops
OAK11:53 pmOakland
$471
Delta
Jan 27
OAK5:55 amOakland
10h 00m
2 stops
MDW5:55 pmChicago Midway
Jan 29
MDW1:49 pmChicago Midway
12h 04m
2 stops
OAK11:53 pmOakland
$490

Southwest flights from Oakland, California to Chicago Midway Airport

Our best Southwest deals on Oakland, California to Chicago Midway Airport flight tickets
Southwest
Apr 18
OAK11:55 pmOakland
4h 05m
MDW6:00 amChicago Midway
Apr 22
MDW8:50 pmChicago Midway
4h 35m
OAK11:25 pmOakland
$217
Southwest
Feb 17
OAK6:30 amOakland
4h 05m
MDW12:35 pmChicago Midway
Feb 24
MDW2:10 pmChicago Midway
7h 40m
1 stop
OAK7:50 pmOakland
$227
Southwest
Feb 17
OAK6:30 amOakland
4h 05m
MDW12:35 pmChicago Midway
Feb 24
MDW8:10 amChicago Midway
8h 45m
2 stops
OAK2:55 pmOakland
$233

momondo Fare Finder

 
Customize your flight search to find flights from Oakland, California to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated January 21, 2026.
Use the filters below to find and compare flights from Oakland, California to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 4/18

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Wed 4/22

8:50 pm-11:25 pm

Nonstop4h 35m

$217

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 2/17

6:30 am-12:35 pm

Nonstop4h 05m

Chicago Midway

Tue 2/24

2:10 pm-7:50 pm

1 stop7h 40m

$227

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 2/17

6:30 am-12:35 pm

Nonstop4h 05m

Chicago Midway

Tue 2/24

8:10 am-2:55 pm

2 stops8h 45m

$233

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 4/18

1:15 pm-9:20 pm

1 stop6h 05m

Chicago Midway

Wed 4/22

4:30 pm-8:45 pm

1 stop6h 15m

$237

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 2/17

4:15 pm-12:25 am

1 stop6h 10m

Chicago Midway

Tue 2/24

8:10 am-2:55 pm

2 stops8h 45m

$242

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 5/5

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Wed 5/13

8:50 pm-11:25 pm

Nonstop4h 35m

$249

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 2/17

6:30 am-12:35 pm

Nonstop4h 05m

Chicago Midway

Thu 3/5

9:30 pm-12:10 am

Nonstop4h 40m

$250

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 2/17

6:30 am-12:35 pm

Nonstop4h 05m

Chicago Midway

Thu 3/5

5:40 pm-10:20 pm

1 stop6h 40m

$256

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 5/2

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Sat 5/16

6:45 am-12:10 pm

1 stop7h 25m

$259

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 2/17

6:30 am-12:35 pm

Nonstop4h 05m

Chicago Midway

Fri 2/20

7:45 am-12:45 pm

1 stop7h 00m

$260

Flights are sorted by cheapest round-trip flights first.

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See travel insights to Chicago from

How to get the cheapest flight ticket from Oakland, California to Chicago Midway 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 cheapest month to fly to Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Oakland, California, with most prices found around $377. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Oakland, California during the month February is also very affordable. Most momondo users find prices during this month for around $378.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Oakland, California. The lowest ticket price found for a Tuesday departure recently was $375. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday 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 $492.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Oakland, California in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $330 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $586. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Oakland to Chicago Midway flight route?

Fly from Oakland to Chicago Midway for the best Oakland - Chicago Midway flight prices

What cabin class options are available on Oakland to Chicago Midway flights?

There is only 1 cabin class available to choose from on Oakland to Chicago Midway 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 Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Oakland, California to Chicago Midway Airport.

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

As of January 2026, prices for Oakland, California to Chicago Midway Airport flights are approximately 13% cheaper when compared to flights at the same time last year.

When to book flights from Oakland, California to Chicago Midway Airport

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

Cheap Oakland, California to Chicago Midway Airport (OAK to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oakland, California to Chicago Midway Airport

Best Price Found

$141

Fastest flight time

4h 00m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Oakland, California in the past 72 hours is $141. The best round-trip flight deal from Oakland, California to Chicago Midway Airport found on momondo in the last 72 hours is $371.
The fastest flight from Oakland, California to Chicago Midway Airport takes 4h 00m
Direct flights go from Oakland, California to Chicago Midway Airport every day.
Search flight deals

  • How far is Oakland to Chicago Midway by plane?

    There are 1839.5 mi between Oakland and Chicago Midway. In terms of flight time, this usually takes a little over 4h 00m.

  • When did momondo last update prices for flights from Oakland Airport to Chicago Midway Airport?

    Prices for flights from Oakland Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Oakland Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Oakland Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Oakland Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Oakland, California to Chicago Midway Airport?

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

Best airlines flying from Oakland, California to Chicago Midway Airport

Compare and see reviews for airlines that fly from Oakland, California to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $271Free CancellationRating
8.0
4,266 reviews
Search Southwest flights

  • Southwest Flights From Oakland, California to Chicago Midway Airport

    Southwest flight deals from Oakland, California to Chicago Midway Airport start from $271 round-trip. Over the 7 Southwest flights for this route in a normal week, average airfare is usually $444 round-trip - but some users have found much cheaper deals with momondo.

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
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
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?

Yes. All flights to Chicago from Oakland on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Oakland to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Oakland. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Oakland to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Oakland are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway Airport trip

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