Southwest® flights from Oakland to Chicago (Midway) from $154*

Fly one-way from Oakland to Chicago (Midway) starting at $154. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

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$154
OFF

Southwest® Flights From Oakland To Chicago (Midway) From $154*

3 weeks from now

Fly one-way from Oakland to Chicago (Midway) starting at $154. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

southwest.com

$109
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$109 CHEAP FLIGHTS From Oakland To Chicago Midway (OAK

3 weeks from now

The cheapest month for flights from Oakland to Chicago Midway Airport is February, where tickets cost $303 (return) on average. On the other hand, the most expensive months are June and …

kayak.com

$133
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$133 Cheap Flights From Oakland (OAK) To Chicago (MDW) - Expedia

3 weeks from now

Cheap Flights from Oakland (OAK) to Chicago (MDW) start at $129 for one-way and $267 for round trip. Earn your airline miles on top of our rewards!

expedia.com

$109
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$109+ Cheap Flights From Oakland, CA (OAK) To Midway (MDW)

3 weeks from now

Find airfare and ticket deals for cheap flights from Oakland, CA to Chicago Midway Airport. Search flight deals from various travel partners with one click at $109. ... Booking flights from …

cheapflights.com

$133
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$133 Flights From Oakland To Chicago (OAK To MDW) - Travelocity

3 weeks from now

$133 Search for cheap flights deals from OAK to MDW (Oakland Intl. to Midway Intl.). We offer cheap direct, non-stop flights including one way and roundtrip tickets.

travelocity.com

$83
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$83 Flights From Oakland (OAK) To Chicago (MDW) | Skyscanner

3 weeks from now

Find the best deals on flights from Oakland Metropolitan Oak (OAK) to Chicago Midway (MDW). Compare prices from hundreds of major travel agents and airlines, all in one search.

skyscanner.com

$67
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$67 Cheap Flights From Oakland To Chicago (OAK To CHI) - Expedia

3 weeks from now

Cheap Flights from Oakland (OAK) to Chicago (CHI) start at $67 for one-way and $109 for round trip. Earn your airline miles on top of our rewards!

expedia.com

$154
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Cheap Flights From Oakland To Chicago From $154 - Jetcost

3 weeks from now

Find flights from Oakland to Chicago (OAK-CHI) with Jetcost. Compare deals from top airlines and travel agencies and find your Oakland - Chicago flight at the best price.

jetcost.com

$38
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$38 Cheap Flights From Oakland To Chicago In 2024/25 - Momondo

3 weeks from now

Search and compare airfare from 1000+ airlines and travel sites to get the cheapest flights from Oakland to Chicago with momondo. ... Fly from Oakland to Chicago Midway for the best …

momondo.com

$108
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Cheap Flights From Oakland (OAKA) To Chicago (CHIA)

3 weeks from now

Outbound direct flight with Southwest Airlines departing from Oakland Metropolitan Oak on Sun, Mar 2, arriving in Chicago Midway. Price includes taxes and charges. From $108, select. Sun, Mar 2 OAK – MDW with Southwest Airlines. Direct. from $108. ... You can easily track the fare of your cheap Oakland–Chicago flights by creating an alert ...

skyscanner.com

$65
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$65 CHEAP FLIGHTS From Oakland To Chicago (OAK - CHI) - KAYAK

3 weeks from now

$65 Find Cheap Flights from Oakland to Chicago. ... Our data shows that the cheapest route for a return flight from Oakland to Chicago cost $317 and was between Oakland (OAK) and Chicago Midway Airport (MDW). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $317.

kayak.com

$54
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$54+ Flights From Oakland, CA To Chicago | Cheapflights

3 weeks from now

5 days ago · Find airfare and ticket deals for cheap flights from Oakland, CA to Chicago. Search flight deals from various travel partners with one click at $54. ... Oakland Chicago. OAK - …

cheapflights.com

$66
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Cheap Flights From Oakland, California To Chicago - FareCompare

3 weeks from now

Find flights from Oakland, California (OAK) to Chicago (CHI) $66+, FareCompare finds cheap flights, and sends email alerts

farecompare.com

3%
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Cheap Flights From Oakland, CA To Chicago, IL - Kiwi.com

3 weeks from now

Up to 3% cash back · Search, compare, and book flights to travel from Oakland, CA to Chicago, IL. Cheap, quick, and easy ways to explore any destination. Discover new …

FAQs about Southwest® flights from Oakland to Chicago (Midway) from $154* Coupon?

How do I book a flight from Oakland to Chicago (Midway)?

To book a flight from Oakland to Chicago (Midway), use Southwest Airlines ®. Find and book your Oakland International Airport to Chicago Midway International Airport flight for a convenient travel experience. Southwest Airlines ® is ideal for both business and pleasure trips, as well as solo and family travel. ...

Which airlines fly from Chicago to Oakland?

Alaska Airlines and Delta are the two airlines most popular with KAYAK users for flights from Chicago to Oakland. ...

What is the earliest flight from Oakland to Chicago Midway Airport?

Early birds can take the earliest flight from Oakland, California at 5:05 am and will be landing in Chicago Midway Airport at 11:05 am. What’s the latest departure time from Oakland to Chicago Midway Airport? If you prefer to fly at night, the latest flight from Oakland, California to Chicago Midway Airport jets off at 7:20 pm and lands at 1:20 am. ...

Which airport is Chicago Midway Airport?

Oakland airport is called Oakland and the only airport in Chicago Midway Airport is Chicago Midway. Which aircraft models fly most regularly from Oakland to Chicago Midway Airport? We unfortunately don’t have that data for this specific route. On which days can I fly direct from Oakland to Chicago Midway Airport? ...

How many nonstop flights are there in Chicago?

Each day, there are between 2 and 3 nonstop flights that take off from Oakland, California and land in Chicago Midway Airport, with an average flight time of 4h 04m. The most common departure time is 5:00 am and most flights take off at night. Each week, there are 16 flights. ...