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Cheap flights from Oakland, California to Chicago from $119

1 adult
1 adult, Economy, 0 bags

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 - 5:55 amOAK  Oakland-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
7:30 pm - 10:10 pmMDW  Chicago Midway-OAK Oakland
4h 40mnonstop
$237Southwest
Tue, Oct 13 - Sat, Oct 17
Southwest Logo
5:50 am - 11:50 amOAK  Oakland-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
8:45 pm - 11:30 pmMDW  Chicago Midway-OAK Oakland
4h 45mnonstop
$237Southwest
Thu, Oct 29 - Tue, Nov 3
Southwest Logo
11:55 pm - 5:55 amOAK  Oakland-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
9:30 pm - 12:10 amMDW  Chicago Midway-OAK Oakland
4h 40mnonstop
$237Southwest
Mon, Sep 28 - Thu, Oct 1
Southwest Logo
11:50 pm - 5:55 amOAK  Oakland-MDW Chicago Midway
4h 05mnonstop
Southwest Logo
12:55 pm - 3:35 pmMDW  Chicago Midway-OAK Oakland
4h 40mnonstop
$237Southwest
Tue, Nov 10 - Sat, Nov 14
Southwest Logo
11:50 pm - 5:55 amOAK  Oakland-MDW Chicago Midway
4h 05mnonstop
Southwest Logo
12:55 pm - 3:35 pmMDW  Chicago Midway-OAK Oakland
4h 40mnonstop
$237Southwest
Wed, Nov 11 - Sat, Nov 14
Southwest Logo
11:55 pm - 5:55 amOAK  Oakland-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
8:35 pm - 11:10 pmMDW  Chicago Midway-OAK Oakland
4h 35mnonstop
$237Southwest
Mon, Sep 21 - Tue, Sep 29
Southwest Logo
11:55 pm - 5:55 amOAK  Oakland-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
8:35 pm - 11:10 pmMDW  Chicago Midway-OAK Oakland
4h 35mnonstop
$237Southwest
Sat, Sep 26 - Tue, Sep 29
Southwest Logo
8:40 pm - 5:40 amOAK  Oakland-MDW Chicago Midway
7h 00m1 stop Las Vegas Harry Reid Intl
Southwest Logo
10:00 am - 12:45 pmMDW  Chicago Midway-OAK Oakland
4h 45mnonstop
$247Southwest
Thu, Oct 29 - Tue, Nov 3
Delta Logo
5:55 am - 8:49 amOAK  Oakland-MDW Chicago Midway
24h 54m2 stops Salt Lake City Minneapolis St Paul
Delta Logo
1:00 pm - 11:56 pmMDW  Chicago Midway-OAK Oakland
12h 56m2 stops Detroit Metropolitan Wayne County Salt Lake City
$350Delta
Tue, Feb 2 - Tue, Feb 9
Delta Logo
5:55 am - 8:49 amOAK  Oakland-MDW Chicago Midway
24h 54m2 stops Salt Lake City Minneapolis St Paul
Delta Logo
1:00 pm - 11:56 pmMDW  Chicago Midway-OAK Oakland
12h 56m2 stops Detroit Metropolitan Wayne County Salt Lake City
$350Delta
Wed, Feb 3 - Tue, Feb 9

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Southwest flights from Oakland, California to Chicago Midway Airport

Our best Southwest deals on Oakland, California to Chicago Midway Airport flight tickets
Southwest
Sep 21
OAK11:55 pmOakland
4h 00m
MDW5:55 amChicago Midway
Sep 29
MDW8:35 pmChicago Midway
4h 35m
OAK11:10 pmOakland
$237
Southwest
Sep 21
OAK11:55 pmOakland
4h 00m
MDW5:55 amChicago Midway
Sep 29
MDW6:00 pmChicago Midway
6h 30m
1 stop
OAK10:30 pmOakland
$247
Southwest
Oct 13
OAK7:15 amOakland
7h 30m
2 stops
MDW4:45 pmChicago Midway
Oct 17
MDW7:30 pmChicago Midway
4h 40m
OAK10:10 pmOakland
$252

Delta flights from Oakland, California to Chicago Midway Airport

Our best Delta deals on Oakland, California to Chicago Midway Airport flight tickets
Delta
Sep 9
OAK6:00 amOakland
8h 57m
2 stops
MDW4:57 pmChicago Midway
Sep 10
MDW9:59 amChicago Midway
8h 21m
2 stops
OAK4:20 pmOakland
$445
Delta
Sep 2
OAK6:00 amOakland
10h 01m
2 stops
MDW6:01 pmChicago Midway
Sep 9
MDW9:59 amChicago Midway
8h 21m
2 stops
OAK4:20 pmOakland
$474
Delta
Sep 8
OAK6:00 amOakland
8h 57m
2 stops
MDW4:57 pmChicago Midway
Sep 12
MDW9:59 amChicago Midway
8h 21m
2 stops
OAK4:20 pmOakland
$486

momondo Fare Finder

 
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 Oakland - MDW Chicago Midway

OAKMDW

Oakland

Tue 10/13

11:55 pm-5:55 am

Nonstop4h 00m

Chicago Midway

Sat 10/17

7:30 pm-10:10 pm

Nonstop4h 40m

$237

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Thu 10/29

5:50 am-11:50 am

Nonstop4h 00m

Chicago Midway

Tue 11/3

8:45 pm-11:30 pm

Nonstop4h 45m

$237

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Mon 9/28

11:55 pm-5:55 am

Nonstop4h 00m

Chicago Midway

Thu 10/1

9:30 pm-12:10 am

Nonstop4h 40m

$237

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Tue 11/10

11:50 pm-5:55 am

Nonstop4h 05m

Chicago Midway

Sat 11/14

12:55 pm-3:35 pm

Nonstop4h 40m

$237

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Wed 11/11

11:50 pm-5:55 am

Nonstop4h 05m

Chicago Midway

Sat 11/14

12:55 pm-3:35 pm

Nonstop4h 40m

$237
Quickest round-trip

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Mon 9/21

11:55 pm-5:55 am

Nonstop4h 00m

Chicago Midway

Tue 9/29

8:35 pm-11:10 pm

Nonstop4h 35m

$237

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Sat 9/26

11:55 pm-5:55 am

Nonstop4h 00m

Chicago Midway

Tue 9/29

8:35 pm-11:10 pm

Nonstop4h 35m

$237

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Thu 10/29

8:40 pm-5:40 am

1 stop7h 00m

Chicago Midway

Tue 11/3

10:00 am-12:45 pm

Nonstop4h 45m

$247

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Tue 2/2

5:55 am-8:49 am

2 stops24h 54m

Chicago Midway

Tue 2/9

1:00 pm-11:56 pm

2 stops12h 56m

$350

OaklandChicago

OAK Oakland - MDW Chicago Midway

OAKMDW

Oakland

Wed 2/3

5:55 am-8:49 am

2 stops24h 54m

Chicago Midway

Tue 2/9

1:00 pm-11:56 pm

2 stops12h 56m

$350

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?

Prices are currently low for flights on this route.

Typical prices usually range from $377 to $548.
The lowest price recently found on this route was $237.

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 December is also very affordable. Most momondo users find prices during this month for around $340.

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 $423. 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 $512.

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 $443 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $474. 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.

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

$119

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 $119. The best round-trip flight deal from Oakland, California to Chicago Midway Airport found on momondo in the last 72 hours is $237.
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 $311Free CancellationRating
8.0
4,201 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 $311 round-trip. Over the 18 Southwest flights for this route in a normal week, average airfare is usually $473 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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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