Cheap flights from Oakland to Chicago
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Travel tip: Don't miss to visit The Renaissance Society in Hyde Park.Check our current prices for flights from Oakland to Chicago. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Oakland to Chicago, you will need to run a search below.
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Cheap Chicago airfares from $133/RT are provided by Cheapoair.com. Outbound flight is leaving on 04/10/2025, 06:54 pm from Oakland Intl (OAK) airport and arrives at Chicago O`hare (ORD) at 06:33 am. The flight time is 11 hours and 39 minutes. The Returning flight departes on 04/22/2025, 10:48 am (other return dates are also available). Date posted: 11 Feb 2025
Price evolution for flights From Oakland To Chicago

Recent Deals on Flights from Oakland to Chicago:Roundtrip / Oneway
- $133
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Oakland, CA (OAK) Chicago, IL (ORD) 04/10/2025 06:54 pm Chicago, IL (ORD) Oakland, CA (OAK) 04/22/2025 10:48 am - $173
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Oakland, CA (OAK) Chicago, IL (ORD) 03/11/2025 05:52 pm Chicago, IL (ORD) Oakland, CA (OAK) 03/25/2025 08:00 am - $201
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Oakland, CA (OAK) Chicago, IL (ORD) 03/23/2025 06:55 pm Chicago, IL (ORD) Oakland, CA (OAK) 04/03/2025 10:19 am - $276
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Oakland, CA (OAK) Chicago, IL (ORD) 03/23/2025 06:55 pm Chicago, IL (ORD) Oakland, CA (OAK) 04/03/2025 08:00 am - $131
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Oakland, CA (OAK) Chicago, IL (ORD) 03/12/2025 05:52 pm - $131
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Oakland, CA (OAK) Chicago, IL (ORD) 04/04/2025 06:55 pm
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