Book Cheap Flights from Chicago with Alaska Airlines
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Find round-trip flight deals from Chicago.*
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Chicago (ORD)to
Seattle (SEA)Sep 19, 2026 - Sep 20, 2026
From
$346
Seen: 6 hours ago
Round-trip
Saver
Chicago (ORD)to
San Diego (SAN)Nov 3, 2026 - Nov 10, 2026
From
$297
Seen: 8 hours ago
Round-trip
Saver
Chicago (ORD)to
Anchorage (ANC)Sep 7, 2026 - Sep 21, 2026
From
$433
Seen: 2 hours ago
Round-trip
Saver
Chicago (ORD)to
Portland (PDX)Sep 23, 2026 - Sep 29, 2026
From
$357
Seen: 1 hour ago
Round-trip
Saver
Chicago (ORD)to
Honolulu (HNL)Oct 19, 2026 - Oct 27, 2026
From
$600
Seen: 2 hours ago
Round-trip
Saver
Chicago (ORD)to
Maui (OGG)Sep 25, 2026 - Oct 3, 2026
From
$784
Seen: 4 hours ago
Round-trip
Saver
Chicago (ORD)to
Las Vegas (LAS)Sep 20, 2026 - Sep 22, 2026
From
$281
Seen: 8 hours ago
Round-trip
Saver
Chicago (ORD)to
Los Angeles (LAX)Oct 1, 2026 - Oct 4, 2026
From
$445
Seen: 4 hours ago
Round-trip
Saver
Chicago (ORD)to
Kona (KOA)Aug 29, 2026 - Sep 5, 2026
From
$733
Seen: 12 hours ago
Round-trip
Saver
Chicago (ORD)to
Fairbanks (FAI)Nov 10, 2026 - Nov 17, 2026
From
$524
Seen: 4 hours ago
Round-trip
Saver
Chicago (ORD)to
Sacramento (SMF)Aug 9, 2026 - Aug 9, 2026
From
$1,333
Seen: 2 hours ago
Round-trip
Saver
Chicago (ORD)to
Lihue (LIH)Nov 8, 2026 - Nov 15, 2026
From
$595
Seen: 9 hours ago
Round-trip
Saver
*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 flight deals from Chicago.*
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From | To | Fare Type | Dates | Price | |
|---|---|---|---|---|---|
| Chicago (ORD) | San Diego (SAN) | One-way | Saver | Depart: Sep 22, 2026 | From $149 Seen: 26 minutes ago | |
| Chicago (ORD) | Boise (BOI) | One-way | Saver | Depart: Sep 23, 2026 | From $163 Seen: 2 hours ago | |
| Chicago (ORD) | San Diego (SAN) | One-way | Saver | Depart: Oct 9, 2026 | From $169 Seen: 17 hours ago | |
| Chicago (ORD) | San Diego (SAN) | One-way | Saver | Depart: Sep 28, 2026 | From $169 Seen: 2 hours ago | |
| Chicago (ORD) | San Diego (SAN) | One-way | Saver | Depart: Sep 13, 2026 | From $169 Seen: 41 minutes ago | |
| Chicago (ORD) | Portland (PDX) | One-way | Saver | Depart: Nov 13, 2026 | From $179 Seen: 3 hours ago | |
| Chicago (ORD) | Seattle (SEA) | One-way | Saver | Depart: Sep 16, 2026 | From $189 Seen: 7 hours ago | |
| Chicago (ORD) | Seattle (SEA) | One-way | Saver | Depart: Dec 2, 2026 | From $189 Seen: 3 hours ago | |
| Chicago (ORD) | Seattle (SEA) | One-way | Saver | Depart: Oct 20, 2026 | From $189 Seen: 12 hours ago | |
| Chicago (ORD) | Seattle (SEA) | One-way | Saver | Depart: Sep 9, 2026 | From $189 Seen: 8 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.