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Cheap flights from Oakland, California to Chicago from $128

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 10/3. 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

Delta Logo
5:55 am - 5:43 pmOAK-MDW
9h 48m2 stops
Delta Logo
6:00 am - 4:11 pmMDW-OAK
12h 11m2 stops
$287Delta
Find Deal
Sat, Oct 25 - Sat, Nov 1
Southwest Logo
5:50 am - 11:55 amOAK-MDW
4h 05mnonstop
Southwest Logo
5:15 am - 10:10 amMDW-OAK
6h 55m1 stop
$297Southwest
Find Deal
Mon, Oct 27 - Wed, Nov 5
Southwest Logo
5:50 am - 11:55 amOAK-MDW
4h 05mnonstop
Southwest Logo
7:05 am - 1:55 pmMDW-OAK
8h 50m2 stops
$302Southwest
Find Deal
Mon, Oct 27 - Wed, Nov 5
Southwest Logo
3:10 pm - 12:25 amOAK-MDW
7h 15m1 stop
Southwest Logo
5:15 am - 9:25 amMDW-OAK
6h 10m1 stop
$307Southwest
Find Deal
Wed, Oct 15 - Sat, Oct 18
Southwest Logo
6:40 am - 12:45 pmOAK-MDW
4h 05mnonstop
Southwest Logo
8:40 am - 1:10 pmMDW-OAK
6h 30m1 stop
$310Southwest
Find Deal
Sun, Oct 19 - Tue, Oct 21
Southwest Logo
3:10 pm - 12:25 amOAK-MDW
7h 15m1 stop
Southwest Logo
5:15 am - 12:05 pmMDW-OAK
8h 50m2 stops
$312Southwest
Find Deal
Wed, Oct 15 - Sat, Oct 18
Southwest Logo
3:10 pm - 12:25 amOAK-MDW
7h 15m1 stop
Southwest Logo
8:25 am - 2:20 pmMDW-OAK
7h 55m1 stop
$317Southwest
Find Deal
Wed, Oct 15 - Sat, Oct 18
Southwest Logo
8:55 am - 5:55 pmOAK-MDW
7h 00m1 stop
Southwest Logo
1:50 pm - 6:15 pmMDW-OAK
6h 25m1 stop
$320Southwest
Find Deal
Fri, Oct 24 - Tue, Oct 28
Southwest Logo
5:25 am - 11:30 amOAK-MDW
4h 05mnonstop
Southwest Logo
7:45 am - 10:25 amMDW-OAK
4h 40mnonstop
$323Southwest
Find Deal
Thu, Nov 13 - Sun, Nov 16
Delta Logo
5:45 am - 6:18 pmOAK-MDW
10h 33m2 stops
Delta Logo
1:14 pm - 12:08 amMDW-OAK
12h 54m2 stops
$327Delta
Find Deal
Sat, Dec 6 - Sun, Dec 7

Delta flights from Oakland, California to Chicago Midway Airport

Our best Delta deals on Oakland, California to Chicago Midway Airport flight tickets
Delta
Oct 25
OAK5:55 amOakland
9h 48m
2 stops
MDW5:43 pmChicago Midway
Nov 1
MDW6:00 amChicago Midway
12h 11m
2 stops
OAK4:11 pmOakland
$287
Find similar
Delta
Dec 6
OAK5:45 amOakland
10h 33m
2 stops
MDW6:18 pmChicago Midway
Dec 7
MDW1:14 pmChicago Midway
12h 54m
2 stops
OAK12:08 amOakland
$327
Find similar
Delta
Oct 22
OAK12:30 pmOakland
27h 13m
2 stops
MDW5:43 pmChicago Midway
Nov 5
MDW9:20 amChicago Midway
16h 33m
2 stops
OAK11:53 pmOakland
$354
Find similar

Southwest flights from Oakland, California to Chicago Midway Airport

Our best Southwest deals on Oakland, California to Chicago Midway Airport flight tickets
Southwest
Oct 27
OAK5:50 amOakland
4h 05m
MDW11:55 amChicago Midway
Nov 5
MDW5:15 amChicago Midway
6h 55m
1 stop
OAK10:10 amOakland
$297
Find similar
Southwest
Oct 27
OAK5:50 amOakland
4h 05m
MDW11:55 amChicago Midway
Nov 5
MDW7:05 amChicago Midway
8h 50m
2 stops
OAK1:55 pmOakland
$302
Find similar
Southwest
Oct 15
OAK3:10 pmOakland
7h 15m
1 stop
MDW12:25 amChicago Midway
Oct 18
MDW5:15 amChicago Midway
6h 10m
1 stop
OAK9:25 amOakland
$307
Find similar

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 September 17, 2025.
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 10/25

5:55 am-5:43 pm

2 stops9h 48m

Chicago Midway

Sat 11/1

6:00 am-4:11 pm

2 stops12h 11m

$287

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 10/27

5:50 am-11:55 am

Nonstop4h 05m

Chicago Midway

Wed 11/5

5:15 am-10:10 am

1 stop6h 55m

$297

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 10/27

5:50 am-11:55 am

Nonstop4h 05m

Chicago Midway

Wed 11/5

7:05 am-1:55 pm

2 stops8h 50m

$302

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 10/15

3:10 pm-12:25 am

1 stop7h 15m

Chicago Midway

Sat 10/18

5:15 am-9:25 am

1 stop6h 10m

$307

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sun 10/19

6:40 am-12:45 pm

Nonstop4h 05m

Chicago Midway

Tue 10/21

8:40 am-1:10 pm

1 stop6h 30m

$310

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 10/15

3:10 pm-12:25 am

1 stop7h 15m

Chicago Midway

Sat 10/18

5:15 am-12:05 pm

2 stops8h 50m

$312

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 10/15

3:10 pm-12:25 am

1 stop7h 15m

Chicago Midway

Sat 10/18

8:25 am-2:20 pm

1 stop7h 55m

$317

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 10/24

8:55 am-5:55 pm

1 stop7h 00m

Chicago Midway

Tue 10/28

1:50 pm-6:15 pm

1 stop6h 25m

$320

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 11/13

5:25 am-11:30 am

Nonstop4h 05m

Chicago Midway

Sun 11/16

7:45 am-10:25 am

Nonstop4h 40m

$323

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 12/6

5:45 am-6:18 pm

2 stops10h 33m

Chicago Midway

Sun 12/7

1:14 pm-12:08 am

2 stops12h 54m

$327

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 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 $364. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Oakland, California during the month October is also very affordable. Most momondo users find prices during this month for around $383.

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

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Oakland, California. The lowest ticket price found for a Thursday departure recently was $395. 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 evening is the least expensive time of day to depart. momondo users have found prices as low as $284 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $535. 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.

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

$219

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 $219. The best round-trip flight deal from Oakland, California to Chicago Midway Airport found on momondo in the last 72 hours is $368.
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 05m.

  • 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 $267Free CancellationRating
8.0
4,242 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 $267 round-trip. Over the 13 Southwest flights for this route in a normal week, average airfare is usually $440 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
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New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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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