Flight Deals from Chicago to Oakland from $98

The flight from Chicago to Oakland is about 1,840 miles. Nonstop service on Southwest typically takes 4 hours 35 minutes outbound, while the return flight to Chicago runs about 4 hours 5 minutes — the westbound leg is the longer one.

Methodology

Flight times and distances come from our flight-schedule database, which combines published airline timetables, U.S. government schedule data from the Bureau of Transportation Statistics (BTS), and observed flight operations from the EUROCONTROL/OpenSky Open Performance Data Initiative (OPDI). The typical flight time is the median scheduled block time across all carriers on the route, computed the same way in both directions so the difference reflects prevailing winds rather than any change in method. Distance is the great-circle distance between the two airports, so the actual flown track is typically 2-5% longer.

Southwest Airlines flies nonstop from Chicago (Midway) to Oakland, with 13 weekly flights running daily. Departures are scheduled at 10:00, 13:20, 21:00, and 21:40.

Methodology

Airlines and weekly frequencies are compiled from our flight-schedule database, which combines published airline timetables, U.S. government schedule data from the Bureau of Transportation Statistics (BTS), and observed flight operations from the EUROCONTROL/OpenSky Open Performance Data Initiative (OPDI). We count each operating carrier's scheduled weekly departures and the days it flies; where there is no nonstop service, connecting carriers are identified by linking scheduled nonstop segments through common hub airports. Where a median fare is shown for a carrier, it reflects the real fares Priceline users found on this route in the last 72 hours.

Oakland International Airport offers taxis, rideshares (Uber, Lyft, and Wingz), public transit, and rental cars. The fastest and most-used option is the BART automated train, which departs every 6 minutes for most of the day and connects to downtown Oakland for $7.85. AC Transit buses 73 and 805 link the airport to the Coliseum BART station for $2.10, with late-night service. Rental cars from Avis, Budget, Enterprise, and Hertz are available at a dedicated center near the airport.

References

• Oakland Airport Bus & Train Transport Guide - iFLYifly.com · Published Jan 15, 2025
• Oakland International Airport - World Travel Guideworldtravelguide.net · Published Mar 31, 2017
• Public Transportation - Oakland San Francisco Bay Airport (OAK)iflyoak.com
• $city_name Airport Code Information $airport_name, $city_namecheapfareguru.com · Published Sep 23, 2025
• Oakland International Airport stationen.wikipedia.org · Published Sep 17, 2025
• OAK Airport Transportation | Black Car, SUV & Van | SuperShuttlesupershuttle.com · Published Apr 20, 2026
• Rideshare - Oakland San Francisco Bay Airport (OAK)iflyoak.com
• How to get from Oakland Airport (OAK) to Oakland, CA | Uberuber.com · Published Sep 5, 2026

Fares from Chicago to Oakland are lowest in early February, around $319. February is the cheapest month overall, averaging $325, followed by January ($327) and October ($345). July is the most expensive month at about $396, and fares peak in late December at about $415. The yearly average is $362. Fares are adjusted to current market conditions.

Methodology

Seasonal fares come from Priceline's own air booking-summary archive, analysed in-house and refreshed monthly. For each day of the year we take a representative round-trip fare, a blend of the 25th-percentile and average ticket price over the route's bookings, and smooth the series into a seasonal curve; the half-month low and high and the monthly figures quoted here are averages of that curve. Thin and international routes borrow their seasonal shape from the nearest busy routes, with the price level anchored to the route's own bookings.

Book about 7 weeks before departure for the best fares from Chicago to Oakland, around $282. Booking in the final days before the flight costs about $421, $139 more. Booking six months ahead runs about $384. Fares are adjusted to current market conditions.

Methodology

Booking-window guidance comes from the same monthly in-house analysis of Priceline's own air booking-summary archive. We aggregate the route's bookings by how many days before departure they were made, from about 180 days out to the day of travel, smooth the curve, and highlight the stretch of lead times with the lowest average fare. Thin and international routes borrow the curve shape from the nearest busy routes, anchored to the route's own price level. It reflects current fares and is refreshed monthly.

Yes, overnight red-eye flights are available from Chicago to Oakland. Southwest operates a nonstop red-eye from Midway to Oakland four nights a week (Monday, Thursday, Friday, and Sunday), departing at 9:40 PM and landing at 12:15 AM in the early hours after midnight.

Methodology

Red-eye flights are identified from scheduled local departure and arrival times and block times in our flight-schedule database — built from published airline timetables and official schedule data, including U.S. Department of Transportation records for domestic routes. A flight counts as a red-eye when it departs in the afternoon or evening (3 p.m. or later local time) or in the early hours before 4 a.m., and is in the air at some point between midnight and 4 a.m. local time at both its departure airport and its arrival airport. An evening flight that lands before midnight at its destination is never counted, nor is a morning departure or a daytime long-haul that reaches the next calendar date only because of time zones. Each red-eye is labelled with its timing (for example, overnight and landing the next morning, or late-night and landing after midnight). For connecting itineraries the same rule is applied to the longer leg, from one representative day's flight search.

Southwest Airlines operates the route from Chicago to Oakland, with 13 nonstop flights weekly from Midway. Flights depart daily at 10:00 AM, 1:20 PM, 9:00 PM, and 9:40 PM. Southwest is not part of a global alliance, and other carriers may serve the route via connecting itineraries.

Methodology

Airlines and weekly frequencies come from our flight-schedule database, which combines published airline timetables, U.S. government schedule data from the Bureau of Transportation Statistics (BTS), and observed flight operations from the EUROCONTROL/OpenSky Open Performance Data Initiative (OPDI). We count each operating carrier's scheduled weekly departures and the days it flies; where there is no nonstop service, connecting carriers are identified by linking scheduled nonstop segments through common hub airports. Where a typical fare is shown for a carrier, it is the median of the real fares Priceline users found on this route in the last 72 hours.

On the Chicago to Oakland route, Southwest Airlines is the most reliable carrier, with an on-time arrival rate of 70.6%. The cancellation rate for Southwest on this route is 0.0%.

Methodology

On-time arrival and cancellation rates come from the U.S. Bureau of Transportation Statistics (BTS) Airline On-Time Performance dataset, which covers U.S. domestic routes only; a flight counts as on time when it arrives within 15 minutes of schedule. Carriers are ranked by arrival on-time rate on this route, and the carrier list itself comes from our flight-schedule database, which combines published airline timetables, U.S. government schedule data from the Bureau of Transportation Statistics (BTS), and observed flight operations from the EUROCONTROL/OpenSky Open Performance Data Initiative (OPDI).

Oakland has one commercial airport: Oakland International Airport (OAK). It is about 10 miles south of downtown Oakland and convenient for San Francisco’s East Bay. Southwest and other low‑cost carriers dominate, making it a strong choice for budget and domestic travel.

Getting to Chicago O'Hare from downtown is easiest and most popular via the CTA Blue Line 'L' train, which runs 24/7 and reaches the airport in about 45 minutes for the lowest fare. Ride-share services like Uber and Lyft, along with taxis, offer door-to-door convenience in roughly 30–40 minutes at a moderate to higher cost. A few shared-ride shuttle and suburban bus options exist, and driving is possible, though parking at O'Hare is generally the priciest and least convenient choice.

References

• Public Transit | Chicago O’Hare International Airport (ORD)flychicago.com:443
• Taxi, Limo, TNP | Chicago O’Hare International Airport (ORD)flychicago.com:443
• Find cheap flights to Chicago (ORD) | American Airlinesaa.com · Published Sep 12, 2026
• How to get from O'Hare Airport (ORD) to Chicago, IL | Uberuber.com · Published Sep 18, 2026
• ord | Qantas AUqantas.com
• ORD Airport Taxi Cab - Request a Ride with Uberuber.com
• O'Hare Flyeren.wikipedia.org · Published Oct 1, 2026
• Transportation in Chicagoen.wikipedia.org · Published Sep 1, 2026

Oakland International Airport has no dedicated sleeping areas, quiet zones, rest zones, or cots for stranded travelers, and overnight stays are limited to landside areas with seating that includes couches and padded armrest-free chairs. There is no hotel directly connected to or on-site at the airport. Nearby hotels include the Holiday Inn Express & Suites Oakland-Airport, Holiday Inn & Suites Oakland-Airport, SpringHill Suites by Marriott Oakland Airport, Courtyard by Marriott Oakland Airport, Hilton Oakland Airport, Hampton Inn & Suites, Home2 Suites by Hilton, and The Marina Inn on San Francisco Bay, many of which offer airport shuttle service.

References

• Oakland International Airport Hotelsworldtravelguide.net · Published May 12, 2024
• Hotels Near Oakland Airport (OAK) · Dymedyme.earth · Published Jun 16, 2026
• Holiday Inn Express & Suites Oakland-Airport Map & Driving Directions | Parking Options for Holiday Inn Express & Suites Oakland-Airport in Oaklandihg.com
• Find Oakland Hotels Near Oakland Intl Airport- Oakland Airport Hotels- Hotel Search by Hotel & Travel Index: Travel Weeklytravelweekly.com · Published Apr 7, 2026
• Holiday Inn & Suites Oakland - Airport | Stress-Free Stays & Parking Near OAK Airport - Stay Park Travelstayparktravel.com · Published Apr 14, 2026
• Courtyard by Marriott Oakland Airport | Hotel with Modern Rooms & Flexible Workspacesmarriott.com · Published Aug 17, 2026
• Oakland Airport Guidesleepinginairports.net · Published Nov 13, 2024
• Oakland Airport Hotel with Shuttle | Holiday Inn & Suites Oakland - Airportihg.com

San Francisco Bay Oakland International Airport offers free Wi-Fi for 45 minutes via the Boingo network, with paid commercial-free high-speed internet also available. Water refill stations and fountains are available throughout both terminals, and mobile charging kiosks are found in both terminals primarily airside, where you can also purchase and exchange FuelRod battery packs. Mamava nursing suites provide private, lockable spaces for feeding and baby care with seating, a fold-down table, and power outlets. Duty-free shopping is available airside in Terminal 1, with additional retail shops scattered throughout both terminals, and a small selection of public art is on display primarily in Terminal 2. SIM cards can be purchased at the InMotion store in Terminal 2. There are no 24-hour dining options, no luggage storage or lockers, and no showers.

References

• Oakland Airport Guidesleepinginairports.net · Published Nov 13, 2024
• OAK Allows Public to Visit Airport Terminals Beyond Security - Oakland San Francisco Bay Airport (OAK)iflyoak.com · Published Dec 15, 2025
• Oakland International Airport Cuts Ribbon on its Great Escapeiflyoak.com · Published Sep 29, 2025

At Chicago O'Hare International Airport, wheelchair assistance is arranged directly through your airline, and travelers can also request help at Airport Information Desks or from Information Ambassadors, who can connect passengers with a live ASL interpreter via video remote interpretation. O'Hare offers a Companion Plus Restroom, wheelchair-accessible restrooms throughout the terminals, service animal relief areas, and a Sunflower program for travelers with non-visible disabilities. For security screening accommodations, TSA Cares can be reached at 855-787-2227.

References

• Terminal Accessibilityflychicago.com:443
• Accessibility Options at O’Hare International Airport (ORD) | Loyola University Chicagoluc.edu
• Accessibility Guide | Chicago O’Hare International Airport (ORD)flychicago.com:443

Southwest Airlines operates the nonstop service from Chicago to Oakland, flying Boeing 737 family aircraft. They are the only carrier currently scheduled nonstop on this route, with flights departing from Midway.

Methodology

Aircraft types come from our flight-schedule database, which combines published airline timetables, U.S. government schedule data from the Bureau of Transportation Statistics (BTS), and observed flight operations from the EUROCONTROL/OpenSky Open Performance Data Initiative (OPDI). For U.S. routes the type is grounded in the tail number that actually operated the flight; elsewhere it comes from the airline's filed equipment code. Where the source does not commit to a specific variant we name the aircraft family (for example Airbus A320 family) rather than guess, and where no reliable type is on file the aircraft is omitted rather than estimated. Types describe typical scheduled equipment and can vary with seasonal or day-of-week assignments and last-minute swaps.

Southwest Airlines is the only carrier currently scheduled nonstop between Chicago (Midway) and Oakland, operating up to 13 weekly daily flights with departures in the morning, afternoon, and evening. Southwest is not a member of any airline alliance, so no alliance offers nonstop service on this route — though other alliances may serve it via connecting itineraries.

Methodology

Airlines and weekly frequencies are compiled from our flight-schedule database, which combines published airline timetables, U.S. government schedule data from the Bureau of Transportation Statistics (BTS), and observed flight operations from the EUROCONTROL/OpenSky Open Performance Data Initiative (OPDI). We count each operating carrier's scheduled weekly departures and the days it flies; where there is no nonstop service, connecting carriers are identified by linking scheduled nonstop segments through common hub airports. Where a median fare is shown for a carrier, it reflects the real fares Priceline users found on this route in the last 72 hours.

Departing from Chicago O'Hare, the United Polaris Lounge in Terminal 1 at Gate C18 is reserved exclusively for United international first and business class passengers, offering a complimentary full-service restaurant, private relaxation areas, and shower suites. United also operates several United Club lounges in Terminals 1 and 2 at gates B6, B18, C10, E7, and F9, open to United Club members and Star Alliance Gold travelers on international itineraries, with amenities like power outlets at every seat, complimentary hot meals, and phone rooms. The American Airlines Flagship Lounge in Terminal 3 requires Concierge Key status or Flagship First on an international flight and features fewer crowds, dedicated service desks, and great airport views. Delta's Sky Club in Terminal 5 at Gate M13 is accessible to Delta One passengers, SkyTeam Elite Plus members on international flights, and Medallion elites in premium cabins, and notably includes a Chicago-style hot dog vendor. The LOT Business Lounge in Terminal 5 at Gate M18 offers floor-to-ceiling airport views, 165 seats, showers, charging stations, and workspaces, with complimentary entry for LOT Business Class and eligible Star Alliance status holders.

References

• List of Airport Lounges at Chicago O'Hare Int'l Airport [ORD]upgradedpoints.com · Published Jul 7, 2026
• The best lounges at Chicago’s O’Hare — and how to get inside - The Points Guythepointsguy.com · Published Apr 4, 2025
• Best Airline Lounges At Chicago O’Hare Airport (ORD) – Luxury Travel Diaryluxurytraveldiary.com · Published Jan 2, 2021
• Airline Lounges | Chicago O’Hare International Airport (ORD)flychicago.com:443
• O'Hare Airport Lounges 2026: Complete Guide + Free Accessjoinkudos.com · Published May 14, 2025
• Airline lounges offer respite at O’Hare International Airport | Choose Chicagochoosechicago.com · Published May 28, 2025
• United Club Chicago - LoungeReview.comloungereview.com · Published Apr 1, 2026
• Swissport Lounge ORD AIRPORT Terminal 5 Chicago IL O Hare Intl | Priority Passprioritypass.com

Same-day changes and standby are possible on this route depending on the airline and fare class, with flexible and premium tickets offering the most reliable options.