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Cheap flights from Oakland, California to Chicago Midway Airport from $99

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 Midway Airport departing on 5/6. 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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Oakland, California to Chicago.
Southwest Logo
6:15 am - 2:10 pmOAK-MDW
5h 55m1 stop
Southwest Logo
4:55 pm - 7:30 pmMDW-OAK
4h 35mnonstop
$207Southwest
Find Deal
Wed, Apr 23 - Sat, Apr 26
Southwest Logo
5:55 am - 12:05 pmOAK-MDW
4h 10mnonstop
Southwest Logo
8:35 am - 1:00 pmMDW-OAK
6h 25m1 stop
$217Southwest
Find Deal
Sun, Apr 27 - Wed, Apr 30
Southwest Logo
5:50 am - 12:00 pmOAK-MDW
4h 10mnonstop
Southwest Logo
4:55 pm - 7:30 pmMDW-OAK
4h 35mnonstop
$227Southwest
Find Deal
Wed, Apr 23 - Sat, Apr 26
Southwest Logo
5:50 am - 12:00 pmOAK-MDW
4h 10mnonstop
Southwest Logo
7:00 pm - 11:25 pmMDW-OAK
6h 25m1 stop
$237Southwest
Find Deal
Tue, Jun 3 - Thu, Jun 12
Southwest Logo
5:55 am - 12:05 pmOAK-MDW
4h 10mnonstop
Southwest Logo
8:40 am - 2:10 pmMDW-OAK
7h 30m1 stop
$247Southwest
Find Deal
Sun, May 4 - Thu, May 8
Southwest Logo
5:55 am - 12:05 pmOAK-MDW
4h 10mnonstop
Southwest Logo
4:55 pm - 7:30 pmMDW-OAK
4h 35mnonstop
$262Southwest
Find Deal
Sun, Apr 27 - Wed, Apr 30
Delta Logo
6:00 am - 5:19 pmOAK-MDW
9h 19m2 stops
Delta Logo
3:02 pm - 10:26 pmMDW-OAK
9h 24m2 stops
$267Delta
Find Deal
Sun, Apr 20 - Sat, Apr 26
Delta Logo
6:00 am - 5:19 pmOAK-MDW
9h 19m2 stops
Delta Logo
9:20 am - 4:15 pmMDW-OAK
8h 55m2 stops
$298Delta
Find Deal
Sat, May 3 - Sat, May 10
Delta Logo
5:10 pm - 9:07 amOAK-MDW
13h 57m2 stops
Delta Logo
1:16 pm - 11:43 pmMDW-OAK
12h 27m2 stops
$307Delta
Find Deal
Fri, Apr 18 - Sun, Apr 20
 Logo
2:07 pm - 10:09 amOAK-MDW
18h 02m2 stops
 Logo
3:03 pm - 4:41 pmMDW-OAK
27h 38m2 stops
Sun, May 11 - Sun, May 18

Southwest flights from Oakland, California to Chicago Midway Airport

Our best Southwest deals on Oakland, California to Chicago Midway Airport flight tickets
Southwest
Apr 23
OAK6:15 amOakland
5h 55m
1 stop
MDW2:10 pmChicago Midway
Apr 26
MDW4:55 pmChicago Midway
4h 35m
OAK7:30 pmOakland
Southwest
Apr 27
OAK5:55 amOakland
4h 10m
MDW12:05 pmChicago Midway
Apr 30
MDW8:35 amChicago Midway
6h 25m
1 stop
OAK1:00 pmOakland
Southwest
Apr 23
OAK5:50 amOakland
4h 10m
MDW12:00 pmChicago Midway
Apr 26
MDW4:55 pmChicago Midway
4h 35m
OAK7:30 pmOakland

Delta flights from Oakland, California to Chicago Midway Airport

Our best Delta deals on Oakland, California to Chicago Midway Airport flight tickets
Delta
Apr 20
OAK6:00 amOakland
9h 19m
2 stops
MDW5:19 pmChicago Midway
Apr 26
MDW3:02 pmChicago Midway
9h 24m
2 stops
OAK10:26 pmOakland
Delta
May 3
OAK6:00 amOakland
9h 19m
2 stops
MDW5:19 pmChicago Midway
May 10
MDW9:20 amChicago Midway
8h 55m
2 stops
OAK4:15 pmOakland
Delta
Apr 18
OAK5:10 pmOakland
13h 57m
2 stops
MDW9:07 amChicago Midway
Apr 20
MDW1:16 pmChicago Midway
12h 27m
2 stops
OAK11:43 pmOakland

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 July is also very affordable. Most momondo users find prices during this month for around $319.

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 $225. 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 $416.

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 $178 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $486. 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.

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

$99

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 $99. The best round-trip flight deal from Oakland, California to Chicago Midway Airport found on momondo in the last 72 hours is $207.
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.

  • 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
4,276 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 6 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?

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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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