$275 Economy Roundtrip to Chicago (OAK-MDW) in May from Oakland

Cheap economy Flights: OAK to MDW in May - Route 3

Starting from $379

Flight Options & Prices:

Direct Flights: From $379 - Fastest option with no layovers
One-Stop Flights: From $379 - Good value with one connection
Multi-Stop Flights: From $379 - Cheapest option with multiple connections

Book your economy class flight from Oakland (OAK) to Chicago (MDW)and save money on your travel. Compare all flight options to find the best deal for your may trip.

Cheap economy Flights: OAK to MDW in May - Route 4

Starting from $395

Flight Options & Prices:

Direct Flights: From $395 - Fastest option with no layovers
One-Stop Flights: From $395 - Good value with one connection
Multi-Stop Flights: From $395 - Cheapest option with multiple connections

Book your economy class flight from Oakland (OAK) to Chicago (MDW)and save money on your travel. Compare all flight options to find the best deal for your may trip.

Cheap economy Flights: OAK to MDW in May - Route 5

Starting from $398

Flight Options & Prices:

Direct Flights: From $398 - Fastest option with no layovers
One-Stop Flights: From $398 - Good value with one connection
Multi-Stop Flights: From $398 - Cheapest option with multiple connections

Book your economy class flight from Oakland (OAK) to Chicago (MDW)and save money on your travel. Compare all flight options to find the best deal for your may trip.

Cheap economy Flights: OAK to MDW in May - Route 6

Starting from $417

Flight Options & Prices:

Direct Flights: From $417 - Fastest option with no layovers
One-Stop Flights: From $417 - Good value with one connection
Multi-Stop Flights: From $417 - Cheapest option with multiple connections

Book your economy class flight from Oakland (OAK) to Chicago (MDW)and save money on your travel. Compare all flight options to find the best deal for your may trip.

Cheap economy Flights: OAK to MDW in May - Route 7

Starting from $437

Flight Options & Prices:

Direct Flights: From $492 - Fastest option with no layovers
One-Stop Flights: From $437 - Good value with one connection
Multi-Stop Flights: From $437 - Cheapest option with multiple connections

Book your economy class flight from Oakland (OAK) to Chicago (MDW)and save money on your travel. Compare all flight options to find the best deal for your may trip.

Best Flights starting from $275

Sat, May 16

Roundtrip

Sat, May 23

Tue, May 19

Roundtrip

Tue, May 26

Sun, May 17

Roundtrip

Sun, May 24

Wed, May 13

Roundtrip

Wed, May 20

Mon, May 18

Roundtrip

Mon, May 25

Fri, May 15

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Fri, May 22

Thu, May 14

Roundtrip

Thu, May 21

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Flight Options & Prices:

Cheap economy Flights: OAK to MDW in May - Route 3

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Cheap economy Flights: OAK to MDW in May - Route 4

Flight Options & Prices:

Cheap economy Flights: OAK to MDW in May - Route 5

Flight Options & Prices:

Cheap economy Flights: OAK to MDW in May - Route 6

Flight Options & Prices:

Cheap economy Flights: OAK to MDW in May - Route 7

Flight Options & Prices:

Why Choose Economy Class Flights from Oakland (OAK) to Chicago (MDW)?