Get data-powered insights and trends into flights from Chicago to Oakland to help you find the cheapest flights, the best time to fly and much more.

Fly one-way from Chicago (Midway) to Oakland starting at $174. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

The best way to get from Chicago to Oakland is to fly which takes 6h 53m and costs $110 - $470. Alternatively, you can train, which costs $190 - $650 and takes 2 days 4h, you could also bus, which costs $170 - $1,100 and takes 2 days 6h.

Fly with Spirit Airlines and get a great deal on flights from Chicago to Oakland, CA / San Francisco, CA AREA. With Spirit's Bare Fare™ You Pay Only the Services You Need!

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Oakland Metropolitan Oak? Find the lowest prices on one-way and round-trip tickets right here.

Flights from Chicago to Oakland. Use Google Flights to plan your next trip and find cheap one way or round trip flights from Chicago to Oakland.

Detailed flight information from Chicago MDW to Oakland OAK. See all airline (s) with scheduled flights and weekly timetables up to 9 months ahead. Flightnumbers and complete route information.

The best one-way flight to Oakland, California from Chicago in the past 72 hours is $46. The best round-trip flight deal from Chicago to Oakland, California found on momondo in the last 72 …

2 days ago · Are you searching for American Airlines flights from Chicago to Oakland? Find the best selections and fly in style.

According to our data, Wednesday is the cheapest day to fly to Oakland, California from Chicago O'Hare Intl Airport. The lowest ticket price found for a Wednesday departure recently was $255. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international.