Book Cheap Flights from Chicago with Alaska Airlines
Find round-trip flight deals from Chicago.*
Chicago (ORD)to
Seattle (SEA)
Chicago (ORD)to
Anchorage (ANC)
Chicago (ORD)to
San Diego (SAN)
Chicago (ORD)to
Portland (PDX)
Chicago (ORD)to
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Vancouver (YVR)*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.*
From | To | Fare Type | Dates | Price | |
|---|---|---|---|---|---|
| Chicago (ORD) | Portland (PDX) | One-way | Saver | Depart: Jun 17, 2026 | From $158 Seen: 6 hours ago | |
| Chicago (ORD) | Portland (PDX) | One-way | Saver | Depart: Jun 20, 2026 | From $168 Seen: 14 hours ago | |
| Chicago (ORD) | Portland (PDX) | One-way | Saver | Depart: Jun 25, 2026 | From $169 Seen: 4 hours ago | |
| Chicago (ORD) | Seattle (SEA) | One-way | Saver | Depart: Aug 8, 2026 | From $178 Seen: 3 hours ago | |
| Chicago (ORD) | Seattle (SEA) | One-way | Saver | Depart: Aug 7, 2026 | From $178 Seen: 11 hours ago | |
| Chicago (ORD) | Seattle (SEA) | One-way | Saver | Depart: Feb 18, 2027 | From $178 Seen: 12 hours ago | |
| Chicago (ORD) | Seattle (SEA) | One-way | Saver | Depart: Oct 4, 2026 | From $178 Seen: 12 hours ago | |
| Chicago (ORD) | Seattle (SEA) | One-way | Saver | Depart: Aug 6, 2026 | From $178 Seen: 11 hours ago | |
| Chicago (ORD) | Seattle (SEA) | One-way | Saver | Depart: Jul 11, 2026 | From $178 Seen: 9 hours ago | |
| Chicago (ORD) | San Diego (SAN) | One-way | Saver | Depart: Jul 9, 2026 | From $179 Seen: 9 hours ago | |
| Chicago (ORD) | San Diego (SAN) | One-way | Saver | Depart: Jul 14, 2026 | From $179 Seen: 11 hours ago | |
| Chicago (ORD) | San Diego (SAN) | One-way | Saver | Depart: Jun 29, 2026 | From $179 Seen: 11 hours ago | |
| Chicago (ORD) | San Diego (SAN) | One-way | Saver | Depart: Jun 28, 2026 | From $179 Seen: 7 hours ago | |
| Chicago (ORD) | San Diego (SAN) | One-way | Saver | Depart: Aug 9, 2026 | From $179 Seen: 5 hours ago | |
| Chicago (ORD) | Redmond (RDM) | One-way | Saver | Depart: Jul 25, 2026 | From $195 Seen: 14 hours ago | |
| Chicago (ORD) | Portland (PDX) | One-way | Saver | Depart: Aug 2, 2026 | From $199 Seen: 12 hours ago | |
| Chicago (ORD) | San Jose (SJC) | One-way | Saver | Depart: Jul 16, 2026 | From $199 Seen: 8 hours ago | |
| Chicago (ORD) | Anchorage (ANC) | One-way | Saver | Depart: Aug 19, 2026 | From $221 Seen: 17 hours ago | |
| Chicago (ORD) | Anchorage (ANC) | One-way | Saver | Depart: Jul 29, 2026 | From $221 Seen: 12 hours ago | |
| Chicago (ORD) | Anchorage (ANC) | One-way | Saver | Depart: Jun 29, 2026 | From $230 Seen: 14 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.