Lowest Priced Flights to Chicago on Alaska Airlines starting at $129*
Most popular flights to Chicago on Alaska Airlines.*
Seattle (SEA)to
Chicago (ORD)Seattle (SEA)to
Chicago (ORD)Seattle (SEA)to
Chicago (ORD)Seattle (SEA)to
Chicago (ORD)Seattle (SEA)to
Chicago (ORD)Portland (PDX)to
Chicago (ORD)Portland (PDX)to
Chicago (ORD)Portland (PDX)to
Chicago (ORD)Portland (PDX)to
Chicago (ORD)Portland (PDX)to
Chicago (ORD)San Diego (SAN)to
Chicago (ORD)San Diego (SAN)to
Chicago (ORD)San Diego (SAN)to
Chicago (ORD)Anchorage (ANC)to
Chicago (ORD)Anchorage (ANC)to
Chicago (ORD)Anchorage (ANC)to
Chicago (ORD)Anchorage (ANC)to
Chicago (ORD)Anchorage (ANC)to
Chicago (ORD)Honolulu (HNL)to
Chicago (ORD)Honolulu (HNL)to
Chicago (ORD)*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.
Top offers for Chicago one-way flights.*
From | To | Fare Type | Dates | Price | |
|---|---|---|---|---|---|
| Oakland (OAK) | Chicago (ORD) | One-way | Saver | Depart: Oct 6, 2026 | From $139 Seen: 6 hours ago | |
| Oakland (OAK) | Chicago (ORD) | One-way | Saver | Depart: Oct 7, 2026 | From $139 Seen: 6 hours ago | |
| Oakland (OAK) | Chicago (ORD) | One-way | Saver | Depart: Oct 13, 2026 | From $139 Seen: 6 hours ago | |
| Oakland (OAK) | Chicago (ORD) | One-way | Saver | Depart: Oct 21, 2026 | From $139 Seen: 6 hours ago | |
| Oakland (OAK) | Chicago (ORD) | One-way | Saver | Depart: Nov 4, 2026 | From $139 Seen: 6 hours ago | |
| Oakland (OAK) | Chicago (ORD) | One-way | Saver | Depart: Oct 20, 2026 | From $139 Seen: 6 hours ago | |
| Los Angeles (LAX) | Chicago (ORD) | One-way | Saver | Depart: Oct 14, 2026 | From $141 Seen: 6 hours ago | |
| Los Angeles (LAX) | Chicago (ORD) | One-way | Saver | Depart: Oct 20, 2026 | From $141 Seen: 6 hours ago | |
| Los Angeles (LAX) | Chicago (ORD) | One-way | Saver | Depart: Oct 27, 2026 | From $141 Seen: 6 hours ago | |
| Los Angeles (LAX) | Chicago (ORD) | One-way | Saver | Depart: Nov 3, 2026 | From $141 Seen: 6 hours ago | |
| Los Angeles (LAX) | Chicago (ORD) | One-way | Saver | Depart: Nov 4, 2026 | From $141 Seen: 6 hours ago | |
| Los Angeles (LAX) | Chicago (ORD) | One-way | Saver | Depart: Nov 9, 2026 | From $141 Seen: 6 hours ago | |
| San Luis Obispo (SBP) | Chicago (ORD) | One-way | Saver | Depart: Nov 14, 2026 | From $143 Seen: 6 hours ago | |
| San Luis Obispo (SBP) | Chicago (ORD) | One-way | Saver | Depart: Oct 6, 2026 | From $143 Seen: 6 hours ago | |
| San Luis Obispo (SBP) | Chicago (ORD) | One-way | Saver | Depart: Oct 27, 2026 | From $143 Seen: 6 hours ago | |
| San Luis Obispo (SBP) | Chicago (ORD) | One-way | Saver | Depart: Nov 4, 2026 | From $143 Seen: 6 hours ago | |
| San Luis Obispo (SBP) | Chicago (ORD) | One-way | Saver | Depart: Nov 10, 2026 | From $143 Seen: 6 hours ago | |
| San Luis Obispo (SBP) | Chicago (ORD) | One-way | Saver | Depart: Oct 20, 2026 | From $143 Seen: 6 hours ago | |
| Spokane (GEG) | Chicago (ORD) | One-way | Saver | Depart: Oct 7, 2026 | From $146 Seen: 6 hours ago | |
| Spokane (GEG) | Chicago (ORD) | One-way | Saver | Depart: Oct 21, 2026 | From $146 Seen: 6 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.
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)