Cheap Flights from Oakland, CA to Chicago, IL from $161

Return flight: Chicago – Oakland

On you will find 1 connecting flights from Oakland to Chicago. You can compare airfare deals from 1 airlines and multiple travel sites from $161, book and save on cheap plane tickets and last minute offers. Also check out OAK-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Oakland to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $161 (one-way), $276 (round-trip).
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Full flight schedule will help you in detecting at what time planes fly from Oakland to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
13:15 — 12:50
+1 day
13:15 — 14:59 AS2644 Alaska Airlines
Oakland — Portland
15h 46m stop
06:45 — 12:50 AS686 Alaska Airlines
Portland — Chicago
21h 35m
including layover
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*Departure and arrival times - local. Updated on May 20, 2024

Flight Information

Below we will explain in detail what the flights cost on the destination from Oakland to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Oakland and Chicago is 2970 miles. Time difference between the cities is 2h. Airplanes depart 13:15 to 13:15 from 3 Oakland airports and arrive 13:15 to 13:15 to 7 Chicago airports. Average flight time is 21h 35m.

  • The fastest flight 21h 35m
  • Average flight time 21h 35m
  • The earliest flight 13:15
  • The latest flight 13:15
  • Distance 1846 ml

The cheapest months to travel to Chicago are may (from 161 $).

What is the lowest airfare Oakland to Chicago?

The cheapest plane ticket found by our users is $161. This airfare is for economy class on one-way AS2644 flight by Alaska Airlines for May 27, 2024 which leaves Oakland Int in Oakland at 13:15 am and arrives at Chicago O'Hare International at 12:50.

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Business class
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Popular Airlines on the Route

The flight Oakland — Chicago is served by 1 regular airline . Most of the flights on this route are operated by Alaska Airlines - 1 departures per week at the price of from $ 161 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 161.

Direct flights

There’re no direct flights on this route. Try flights with stops.

Connecting Flights

There are 1 flights with layovers on the route. The fastest connecting flight is AS2644 by Alaska Airlines takes 21h 35m and the cheapest is AS2644 by Alaska Airlines for $161.

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You can fly from Oakland to Chicago from 3 airports (Oakland Int, Oakland/Coliseum Stat, Convention Center Heliport).

Oakland airports

  • Oakland Int-OAK
    from $161
  • Oakland/Coliseum Stat-OBT
  • Convention Center Heliport-JCE

Chicago airports

  • O'Hare International-ORD
  • Midway-MDW
  • Dupage County-DPA
  • Chicago FSS-CHI
  • Merrill C Meigs (closed)-CGX
  • Pal-Waukee-PWK
  • Chicago NAS-NOH

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.