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Cheap flights from Oakland, California to Chicago from $107

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 8/25. 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
2:30 pm - 11:45 pm
OAK
-
MDW
7h 15m
1 stop
Southwest Logo
8:25 pm - 10:55 pm
MDW
-
OAK
4h 30mnonstop
$353Southwest
Thu, Aug 20 - Sun, Aug 23
Southwest Logo
5:15 am - 2:35 pm
OAK
-
MDW
7h 20m
2 stops
Southwest Logo
12:15 pm - 5:10 pm
MDW
-
OAK
6h 55m
1 stop
$354Southwest
Wed, Jul 8 - Sat, Jul 11
Southwest Logo
9:00 pm - 5:25 am
OAK
-
MDW
6h 25m
1 stop
Southwest Logo
8:15 pm - 12:20 am
MDW
-
OAK
6h 05m
1 stop
$355Southwest
Tue, Jul 7 - Fri, Jul 10
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
5:35 am - 9:50 am
MDW
-
OAK
6h 15m
1 stop
$356Southwest
Sat, Jun 27 - Wed, Jul 1
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
1:20 pm - 3:50 pm
MDW
-
OAK
4h 30mnonstop
$358Southwest
Tue, Jul 21 - Sat, Jul 25
Southwest Logo
5:15 am - 2:35 pm
OAK
-
MDW
7h 20m
2 stops
Southwest Logo
10:10 am - 3:40 pm
MDW
-
OAK
7h 30m
2 stops
$359Southwest
Wed, Jul 8 - Wed, Jul 15
Southwest Logo
7:45 pm - 4:40 am
OAK
-
MDW
6h 55m
1 stop
Southwest Logo
6:40 pm - 11:25 pm
MDW
-
OAK
6h 45m
1 stop
$360Southwest
Sun, Jul 5 - Wed, Jul 8
Southwest Logo
5:15 am - 2:35 pm
OAK
-
MDW
7h 20m
2 stops
Southwest Logo
8:15 pm - 12:20 am
MDW
-
OAK
6h 05m
1 stop
$361Southwest
Wed, Jul 8 - Mon, Jul 13
Southwest Logo
8:15 pm - 5:25 am
OAK
-
MDW
7h 10m
1 stop
Southwest Logo
9:40 pm - 12:10 am
MDW
-
OAK
4h 30mnonstop
$363Southwest
Thu, Jul 2 - Fri, Jul 3
Southwest Logo
8:15 pm - 5:25 am
OAK
-
MDW
7h 10m
1 stop
Southwest Logo
5:10 am - 10:20 am
MDW
-
OAK
7h 10m
1 stop
$364Southwest
Mon, Jun 22 - Thu, Jun 25

Southwest flights from Oakland, California to Chicago Midway Airport

Our best Southwest deals on Oakland, California to Chicago Midway Airport flight tickets
Southwest
Sep 10
OAK8:30 pmOakland
6h 00m
1 stop
MDW4:30 amChicago Midway
Sep 13
MDW5:40 amChicago Midway
6h 30m
1 stop
OAK10:10 amOakland
$353
Southwest
Jun 29
OAK8:30 pmOakland
6h 10m
1 stop
MDW4:40 amChicago Midway
Jul 3
MDW9:40 pmChicago Midway
4h 30m
OAK12:10 amOakland
$354
Southwest
Jul 7
OAK9:00 pmOakland
6h 25m
1 stop
MDW5:25 amChicago Midway
Jul 10
MDW8:15 pmChicago Midway
6h 05m
1 stop
OAK12:20 amOakland
$355

Delta flights from Oakland, California to Chicago Midway Airport

Our best Delta deals on Oakland, California to Chicago Midway Airport flight tickets
Delta
Sep 6
OAK6:00 amOakland
8h 59m
2 stops
MDW4:59 pmChicago Midway
Sep 12
MDW9:20 amChicago Midway
9h 11m
2 stops
OAK4:31 pmOakland
$357
Delta
Sep 24
OAK6:00 amOakland
10h 33m
2 stops
MDW6:33 pmChicago Midway
Sep 28
MDW1:00 pmChicago Midway
12h 59m
2 stops
OAK11:59 pmOakland
$366
Delta
Sep 22
OAK6:00 amOakland
10h 33m
2 stops
MDW6:33 pmChicago Midway
Sep 25
MDW6:05 amChicago Midway
12h 18m
2 stops
OAK4:23 pmOakland
$375

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 June 1, 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

Cheapest round-trip

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 8/20

2:30 pm-11:45 pm

1 stop7h 15m

Chicago Midway

Sun 8/23

8:25 pm-10:55 pm

Nonstop4h 30m

$353

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 7/8

5:15 am-2:35 pm

2 stops7h 20m

Chicago Midway

Sat 7/11

12:15 pm-5:10 pm

1 stop6h 55m

$354

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 7/7

9:00 pm-5:25 am

1 stop6h 25m

Chicago Midway

Fri 7/10

8:15 pm-12:20 am

1 stop6h 05m

$355

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 6/27

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Wed 7/1

5:35 am-9:50 am

1 stop6h 15m

$356
Quickest round-trip

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 7/21

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Sat 7/25

1:20 pm-3:50 pm

Nonstop4h 30m

$358

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 7/8

5:15 am-2:35 pm

2 stops7h 20m

Chicago Midway

Wed 7/15

10:10 am-3:40 pm

2 stops7h 30m

$359

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sun 7/5

7:45 pm-4:40 am

1 stop6h 55m

Chicago Midway

Wed 7/8

6:40 pm-11:25 pm

1 stop6h 45m

$360

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 7/8

5:15 am-2:35 pm

2 stops7h 20m

Chicago Midway

Mon 7/13

8:15 pm-12:20 am

1 stop6h 05m

$361

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 7/2

8:15 pm-5:25 am

1 stop7h 10m

Chicago Midway

Fri 7/3

9:40 pm-12:10 am

Nonstop4h 30m

$363

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 6/22

8:15 pm-5:25 am

1 stop7h 10m

Chicago Midway

Thu 6/25

5:10 am-10:20 am

1 stop7h 10m

$364

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest 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 typical price of a round-trip flight between Oakland, California and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Oakland, California, with most prices found around $288. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Oakland, California during the month September is also very affordable. Most momondo users find prices during this month for around $377.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Oakland, California. The lowest ticket price found for a Wednesday departure recently was $416. 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 $497.

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 in the morning because they tend to be around $449. 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, California to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Oakland, California to Chicago Midway Airport 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 Midway Airport flight prices changed over time?

As of June 2026, prices for Oakland, California to Chicago Midway Airport flights are approximately 99% more expensive 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

$250

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 $250. The best round-trip flight deal from Oakland, California to Chicago Midway Airport found on momondo in the last 72 hours is $454.
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

Frequently asked questions about flying from Oakland, California to Chicago Midway Airport

  • 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 $288Free CancellationRating
8.0
4,261 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 $288 round-trip. Over the 8 Southwest flights for this route in a normal week, average airfare is usually $482 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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.

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