Southwest® flights from San Diego to Chicago (O'Hare) from $181*

Fly one-way from San Diego to Chicago (O'Hare) starting at $181. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

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$181
OFF

Southwest® Flights From San Diego To Chicago (O'Hare) From $181*

2 weeks from now

Fly one-way from San Diego to Chicago (O'Hare) starting at $181. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

southwest.com

$70
OFF

Southwest Flights To Chicago O'Hare Intl Airport (ORD) From $70

2 weeks from now

Find and compare Southwest flights to Chicago O'Hare Intl Airport (ORD). Fly from the United States with Southwest to Chicago O'Hare Intl Airport. From Baltimore $70; From New York …

kayak.com

$33
OFF

$33 Flights From San Diego (SAN) To Chicago (ORD) - Skyscanner

2 weeks from now

Find the best deals on flights from San Diego International (SAN) to Chicago O'Hare International (ORD). Compare prices from hundreds of major travel agents and airlines, all in one search. ...

skyscanner.com

$74
OFF

$74+ Cheap Flights From San Diego (SAN) To O'Hare Intl (ORD)

2 weeks from now

3 days ago · Currently, August is the cheapest month in which you can book a flight from San Diego to Chicago O'Hare Intl Airport (average of $245). Flying from San Diego to Chicago …

cheapflights.com

$757
OFF

Cheap Flights From San Diego To Chicago O'Hare Intl Airport From

2 weeks from now

Alaska Airlines Flights From San Diego to Chicago O'Hare Intl Airport. Across 18 Alaska Airlines flights from San Diego to Chicago O'Hare Intl Airport this week, the average price was $757, …

momondo.com

$33
OFF

$33 Cheap Flights From San Diego (SAN) To Chicago (ORD)

2 weeks from now

Cheap Flights from San Diego (SAN) to Chicago (ORD) start at $33 for one-way and $66 for round trip. Earn your airline miles on top of our rewards!

expedia.com

$226
OFF

Southwest® Flights From Chicago (O'Hare) To San Diego From $226*

2 weeks from now

Fly one-way from Chicago (O'Hare) to San Diego starting at $226. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

southwest.com

$184
OFF

Cheap Flights From San Antonio To Chicago (O'Hare) From $184 ...

2 weeks from now

Fly one-way from San Antonio to Chicago (O'Hare) starting at $184. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

southwest.com