Book Cheap Flights from Chicago with Alaska Airlines
Find round-trip flight deals from Chicago.*
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Santa Ana (SNA)*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) | San Diego (SAN) | One-way | Saver | Depart: May 20, 2026 | From $119 Seen: 17 hours ago | |
| Chicago (ORD) | San Diego (SAN) | One-way | Saver | Depart: May 19, 2026 | From $119 Seen: 4 hours ago | |
| Chicago (ORD) | San Diego (SAN) | One-way | Saver | Depart: May 16, 2026 | From $119 Seen: 6 hours ago | |
| Chicago (ORD) | San Diego (SAN) | One-way | Saver | Depart: May 27, 2026 | From $119 Seen: 5 hours ago | |
| Chicago (ORD) | San Diego (SAN) | One-way | Saver | Depart: Jun 6, 2026 | From $129 Seen: 5 hours ago | |
| Chicago (ORD) | San Luis Obispo (SBP) | One-way | Saver | Depart: May 30, 2026 | From $138 Seen: 10 hours ago | |
| Chicago (ORD) | San Luis Obispo (SBP) | One-way | Saver | Depart: May 23, 2026 | From $138 Seen: 10 hours ago | |
| Chicago (ORD) | San Luis Obispo (SBP) | One-way | Saver | Depart: May 27, 2026 | From $138 Seen: 10 hours ago | |
| Chicago (ORD) | San Luis Obispo (SBP) | One-way | Saver | Depart: Jun 2, 2026 | From $138 Seen: 10 hours ago | |
| Chicago (ORD) | San Luis Obispo (SBP) | One-way | Saver | Depart: Jun 9, 2026 | From $138 Seen: 10 hours ago | |
| Chicago (ORD) | Spokane (GEG) | One-way | Saver | Depart: Jun 3, 2026 | From $139 Seen: 10 hours ago | |
| Chicago (ORD) | Spokane (GEG) | One-way | Saver | Depart: May 27, 2026 | From $139 Seen: 10 hours ago | |
| Chicago (ORD) | Spokane (GEG) | One-way | Saver | Depart: Jun 2, 2026 | From $139 Seen: 10 hours ago | |
| Chicago (ORD) | Spokane (GEG) | One-way | Saver | Depart: May 20, 2026 | From $139 Seen: 10 hours ago | |
| Chicago (ORD) | San Luis Obispo (SBP) | One-way | Saver | Depart: May 20, 2026 | From $143 Seen: 10 hours ago | |
| Chicago (ORD) | Boise (BOI) | One-way | Saver | Depart: May 24, 2026 | From $148 Seen: 10 hours ago | |
| Chicago (ORD) | Spokane (GEG) | One-way | Saver | Depart: May 24, 2026 | From $148 Seen: 10 hours ago | |
| Chicago (ORD) | Spokane (GEG) | One-way | Saver | Depart: May 28, 2026 | From $148 Seen: 10 hours ago | |
| Chicago (ORD) | Oakland (OAK) | One-way | Saver | Depart: May 28, 2026 | From $148 Seen: 16 hours ago | |
| Chicago (ORD) | San Diego (SAN) | One-way | Saver | Depart: May 22, 2026 | From $149 Seen: 56 minutes 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.