Oakland to Chicago Flight Tickets

Compare the best flight deals from Oakland to Chicago

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About Oakland - Chicago Flights

Find the best prices for flights between Oakland (United States) and Chicago (United States) on Tripuck. We compare prices from hundreds of airlines to offer you the best options.

Oakland has 1 airports, while Chicago has 6 airports. Compare flights between all airports to find the best deal.

Cheapest Months for Oakland - Chicago Flights

Popular Oakland - Chicago Flights

Airlines on Oakland - Chicago Route

Oakland Airports

Chicago Airports

Alternative Routes

Oakland - Chicago Flight Summary

AIRLINES
Southwest Airlines

Cheaper tickets are usually available on weekdays and with early bookings.

Oakland and Chicago - Airport Transportation

Oakland San Francisco Bay Airport (OAK)

How to Get to the Airport

Metro/Train (BART + OAK Line): From downtown Oakland (e.g., 12th St./Oakland City Center or 19th St. Oakland stations), you can take BART to Coliseum BART Station. This journey takes approximately 10-12 minutes. BART operates from 05:00-00:00 on weekdays, 06:00-00:00 on Saturdays, and 08:00-00:00 on Sundays. From Coliseum, transfer to the 'BART to OAK' train to reach the airport in 8-9 minutes.


Bus (AC Transit Connection – Line 73): There is no direct daytime bus line from downtown Oakland to the airport; however, you can first reach Coliseum/OAK BART Station by BART or bus from the center and then take AC Transit Line 73 to the airport. You can reach Coliseum from downtown by BART in 10-12 minutes, then reach the airport in approximately 15-20 minutes via Line 73.


Taxi/Uber/Lyft: Transportation from downtown to the airport is possible via taxi or Uber/Lyft. This journey generally takes 20-30 minutes, depending on traffic conditions.


Car Rental: You can easily reach the airport by renting a car from car rental offices located in the city center.


Private Transfer Services: Many private transfer companies offer a comfortable and fast transportation option from downtown to the airport.

O'Hare International Airport (ORD)

From Airport to City Center

Metro/Train: The CTA Blue Line Train is the most convenient option for transportation from O'Hare International Airport to downtown Chicago. The airport station is directly connected to Terminals 1, 2, and 3. Access from Terminal 5 is possible via a free shuttle train. The journey takes approximately 40-45 minutes. Services operate 24 hours a day, with trains running every 5-10 minutes during peak hours.


Bus (CTA and Private Shuttles): Buses connecting O'Hare Terminals 1, 2, 3, and 5 operate routes to downtown. The journey time varies between 45-60 minutes depending on traffic conditions. Services run every 15-30 minutes and generally operate from 5:00 AM to 11:45 PM.


Taxi: Official taxi stands at O'Hare are located at each terminal exit and provide direct transportation to downtown. The journey time varies between 30-60 minutes depending on traffic. Taxi services are available 24 hours a day.


Airport App-Based Rides (Uber/Lyft): Apps like Uber and Lyft operate in designated pickup areas at O'Hare. Journey time and cost can vary based on traffic and demand.


Car Rental: Various car rental companies are available at the airport. Car rental options can be arranged at offices located at terminal exits or at rental centers accessible via shuttle services.

Frequently Asked Questions About Oakland - Chicago Flights

Oakland to Chicago flight ticket prices vary depending on the season, airline, and how far in advance you book. Use the search form above to see the latest prices.
For Oakland, you can use Oakland San Francisco Bay Airport (OAK). For Chicago, you can use Meigs Airport (CGX), Chicago Rockford International Airport (RFD), Chicago Executive Airport (PWK), Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), DuPage Airport (DPA).
The flight duration from Oakland to Chicago varies for direct flights. Connecting flights may take longer depending on the number of layovers.
Southwest Airlines operate direct flights from Oakland to Chicago.
Generally, off-season periods and weekdays offer more affordable tickets. Booking early can also help you save on prices.
Various airlines operate on this route. Search to see the latest prices.