Alaska Airlines Flights from San Diego to Chicago

Lowest fares from San Diego to Chicago

Apr 2026
From$334*
Seen: 18 hours ago
Flight Type One Way|Saver
May 2026
From$119*
Seen: 2 hours ago
Flight Type One Way|Saver
Jun 2026
From$66*
Seen: 21 hours ago
Flight Type One Way|Saver
$119
$394
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    • Range$119-$394

    *Displayed prices have been available within the past 24 hours and may not be available at the time of booking. Fares listed may be Saver fares, which is our most restrictive fare option and subject to additional restrictions. For roundtrip journeys, the price displayed—available within the past 24 hours—is the aggregate of the lowest available fare each way. Additional baggage charges and fees for optional products and services may apply. Other terms and conditions may apply.

    One-way low-fare flights San Diego to Chicago.*

    $
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    One-way low-fare flights San Diego to Chicago.*
    From
    To
    Fare Type
    Dates
    Price
    San Diego (SAN)Chicago (ORD)One-way
    |
    Saver    		Depart: May 16, 2026

    From

    $119

    Seen: 4 hours ago

    San Diego (SAN)Chicago (ORD)One-way
    |
    Saver    		Depart: May 9, 2026

    From

    $119

    Seen: 6 hours ago

    San Diego (SAN)Chicago (ORD)One-way
    |
    Saver    		Depart: May 23, 2026

    From

    $119

    Seen: 3 hours ago

    San Diego (SAN)Chicago (ORD)One-way
    |
    Saver    		Depart: May 12, 2026

    From

    $119

    Seen: 2 hours ago

    San Diego (SAN)Chicago (ORD)One-way
    |
    Saver    		Depart: Jun 3, 2026

    From

    $119

    Seen: 50 minutes ago

    San Diego (SAN)Chicago (ORD)One-way
    |
    Saver    		Depart: Jun 14, 2026

    From

    $66

    Seen: 21 hours ago

    San Diego (SAN)Chicago (ORD)One-way
    |
    Saver    		Depart: Aug 29, 2026

    From

    $66

    Seen: 16 hours ago

    San Diego (SAN)Chicago (ORD)One-way
    |
    Saver    		Depart: May 5, 2026

    From

    $119

    Seen: 15 hours ago

    *Displayed prices have been available within the past 24 hours and may not be available at the time of booking. Fares listed may be Saver fares, which is our most restrictive fare option and subject to additional restrictions. For roundtrip journeys, the price displayed—available within the past 24 hours—is the aggregate of the lowest available fare each way. Additional baggage charges and fees for optional products and services may apply. Other terms and conditions may apply.

    Explore Alaska Airlines's Flights to Top-Pick Destinations