Lowest Priced Flights to Chicago on Alaska Airlines starting at $139*
Most popular flights to Chicago on Alaska Airlines.*
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Chicago (ORD)Top offers for Chicago one-way flights.*
From | To | Fare Type | Dates | Price | |
|---|---|---|---|---|---|
| Oakland (OAK) | Chicago (ORD) | One-way | Saver | Depart: Sep 21, 2026 | From $139 Seen: 14 hours ago | |
| Oakland (OAK) | Chicago (ORD) | One-way | Saver | Depart: Sep 28, 2026 | From $139 Seen: 14 hours ago | |
| Oakland (OAK) | Chicago (ORD) | One-way | Saver | Depart: Oct 5, 2026 | From $139 Seen: 14 hours ago | |
| Oakland (OAK) | Chicago (ORD) | One-way | Saver | Depart: Oct 15, 2026 | From $139 Seen: 14 hours ago | |
| Oakland (OAK) | Chicago (ORD) | One-way | Saver | Depart: Oct 20, 2026 | From $139 Seen: 14 hours ago | |
| Oakland (OAK) | Chicago (ORD) | One-way | Saver | Depart: Oct 27, 2026 | From $139 Seen: 14 hours ago | |
| San Diego (SAN) | Chicago (ORD) | One-way | Saver | Depart: Sep 23, 2026 | From $139 Seen: 10 hours ago | |
| San Diego (SAN) | Chicago (ORD) | One-way | Saver | Depart: Dec 10, 2026 | From $139 Seen: 4 hours ago | |
| San Diego (SAN) | Chicago (ORD) | One-way | Saver | Depart: Nov 9, 2026 | From $139 Seen: 46 minutes ago | |
| San Diego (SAN) | Chicago (ORD) | One-way | Saver | Depart: Oct 21, 2026 | From $139 Seen: 5 hours ago |
Plan a trip to Chicago
Along the shores of Lake Michigan sits Chicago, a city famous for deep dish pizzas, Oprah, and a huge round metal sculpture called "The Bean" that reflects the Chicago skyline. Chicago was incorporated in 1837 and grew to become the third largest US city. In 1871, the Great Fire destroyed a large section of town; in gutsy Chicago fashion, the city responded by building the first skyscraper in 1884. Glide along the Chicago River on an architecture boat cruise and discover which city buildings are topped with gold. Watch an aardvark nose around for food or see a white cheeked gibbon swing through the trees at the admission-free Lincoln Park Zoo. Come face to face with larger-than-life images of Chicago residents at the interactive Crown Fountain in Millennium Park.
View airport information for Chicago (ORD)