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Cheap flights from Oakland, California to Chicago from $57

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 10/21. 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

Southwest Logo
8:30 pm - 5:10 amOAK-MDW
6h 40m1 stop
Southwest Logo
12:50 pm - 6:25 pmMDW-OAK
7h 35m1 stop
$165Southwest
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Tue, Aug 5 - Tue, Aug 12
Logo
6:00 am - 8:52 pmOAK-MDW
12h 52m1 stop
Logo
7:03 pm - 11:32 pmMDW-OAK
6h 29m1 stop
$173
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Fri, Sep 26 - Mon, Sep 29
Southwest Logo
6:00 am - 2:40 pmOAK-MDW
6h 40m1 stop
Southwest Logo
6:15 am - 10:20 amMDW-OAK
6h 05m1 stop
$181Southwest
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Thu, Jul 31 - Sat, Aug 9
Southwest Logo
6:00 am - 2:40 pmOAK-MDW
6h 40m1 stop
Southwest Logo
8:25 am - 3:05 pmMDW-OAK
8h 40m2 stops
$186Southwest
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Thu, Jul 31 - Sat, Aug 9
Southwest Logo
1:10 pm - 9:50 pmOAK-MDW
6h 40m1 stop
Southwest Logo
1:15 pm - 3:45 pmMDW-OAK
4h 30mnonstop
$207Southwest
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Wed, Aug 20 - Fri, Aug 22
Southwest Logo
11:20 am - 8:50 pmOAK-MDW
7h 30m2 stops
Southwest Logo
1:15 pm - 3:45 pmMDW-OAK
4h 30mnonstop
$212Southwest
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Wed, Aug 20 - Fri, Aug 22
Delta Logo
6:00 am - 5:35 pmOAK-MDW
9h 35m2 stops
Delta Logo
1:43 pm - 10:48 pmMDW-OAK
11h 05m2 stops
$267Delta
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Tue, Sep 30 - Sat, Oct 4
Logo
8:13 am - 10:08 amOAK-MDW
23h 55m2 stops
Logo
6:31 pm - 11:27 pmMDW-OAK
30h 56m2 stops
$296
Find Deal
Thu, Aug 21 - Sun, Aug 24
Delta Logo
12:30 pm - 9:36 amOAK-MDW
19h 06m2 stops
Delta Logo
9:31 am - 11:50 pmMDW-OAK
16h 19m2 stops
$335Delta
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Fri, Aug 8 - Tue, Aug 12
Delta Logo
12:30 pm - 9:36 amOAK-MDW
19h 06m2 stops
Delta Logo
9:15 am - 11:50 pmMDW-OAK
16h 35m2 stops
$347Delta
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Fri, Aug 8 - Wed, Aug 13

Southwest flights from Oakland, California to Chicago Midway Airport

Our best Southwest deals on Oakland, California to Chicago Midway Airport flight tickets
Southwest
Aug 5
OAK8:30 pmOakland
6h 40m
1 stop
MDW5:10 amChicago Midway
Aug 12
MDW12:50 pmChicago Midway
7h 35m
1 stop
OAK6:25 pmOakland
$165
Find similar
Southwest
Jul 31
OAK6:00 amOakland
6h 40m
1 stop
MDW2:40 pmChicago Midway
Aug 9
MDW6:15 amChicago Midway
6h 05m
1 stop
OAK10:20 amOakland
$181
Find similar
Southwest
Jul 31
OAK6:00 amOakland
6h 40m
1 stop
MDW2:40 pmChicago Midway
Aug 9
MDW8:25 amChicago Midway
8h 40m
2 stops
OAK3:05 pmOakland
$186
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Delta flights from Oakland, California to Chicago Midway Airport

Our best Delta deals on Oakland, California to Chicago Midway Airport flight tickets
Delta
Sep 30
OAK6:00 amOakland
9h 35m
2 stops
MDW5:35 pmChicago Midway
Oct 4
MDW1:43 pmChicago Midway
11h 05m
2 stops
OAK10:48 pmOakland
$267
Find similar
Delta
Aug 8
OAK12:30 pmOakland
19h 06m
2 stops
MDW9:36 amChicago Midway
Aug 12
MDW9:31 amChicago Midway
16h 19m
2 stops
OAK11:50 pmOakland
$335
Find similar
Delta
Aug 8
OAK12:30 pmOakland
19h 06m
2 stops
MDW9:36 amChicago Midway
Aug 13
MDW9:15 amChicago Midway
16h 35m
2 stops
OAK11:50 pmOakland
$347
Find similar

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 October is, on average, the cheapest month to fly to Chicago Midway Airport from Oakland, California, with most prices found around $308. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Oakland, California during the month February is also very affordable. Most momondo users find prices during this month for around $364.

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

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Oakland, California. The lowest ticket price found for a Friday departure recently was $358. 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 $522.

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 are 1 cabin classes 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

$57

Fastest flight time

4h 05m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Oakland, California in the past 72 hours is $57. The best round-trip flight deal from Oakland, California to Chicago Midway Airport found on momondo in the last 72 hours is $165.
The fastest flight from Oakland, California to Chicago Midway Airport takes 4h 05m
Direct flights go from Oakland, California to Chicago Midway Airport every day.
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  • 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 $271Free CancellationRating
8.0
4,250 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 $416 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
Crown Point
Munster
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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