Cheap Flights from Chicago to Oakland (MDW to OAK)

Planning a trip from Chicago to Oakland? Globitude Travels helps you secure great fares from Chicago Midway (MDW) to San Francisco Bay Oakland International Airport (OAK). Whether you are visiting Northern California for business, sightseeing, or family, reserve your seat with top carriers like Southwest Airlines and Frontier Airlines today for a seamless cross-country journey.

📞 Call 1-856-513-6369

Fly from Chicago Midway to Oakland

Flying from Chicago Midway Airport to Oakland is a convenient way to reach the East Bay and the broader San Francisco Bay Area. Midway offers an easy-to-navigate departure experience, while Oakland International Airport places you minutes away from vibrant Northern California attractions, tech hubs, and scenic coastal destinations.

Oakland boasts a mild Mediterranean climate year-round, making it an inviting destination in any season. Explore dynamic neighborhoods like Jack London Square and Temescal, sample renowned farm-to-table cuisine, or head across the bay to San Francisco. Booking your tickets through Globitude Travels helps ensure you lock in competitive Economy fares on airlines like Southwest and Frontier.

Money-saving tips for this route

Book your tickets at least three to four weeks in advance to secure the lowest Economy fares.
Travel on mid-week days like Tuesday or Wednesday when demand and airfares are generally lower.
Review airline baggage policies before packing to minimize extra carry-on or checked bag fees.
Take advantage of the BART train connection at Oakland Airport for easy, affordable transit into downtown Oakland or San Francisco.

Frequently asked questions

Which airlines offer flights from Chicago Midway (MDW) to Oakland (OAK)?

Southwest Airlines and Frontier Airlines operate flights on the route from Chicago Midway to Oakland.

What is the starting fare for flights from MDW to OAK?

Economy fares on Southwest Airlines start from $305, while Frontier Airlines offers Economy fares starting from $481.

What are the main airports served on this route?

Flights depart from Chicago Midway International Airport (MDW) in Illinois and land at San Francisco Bay Oakland International Airport (OAK) in California.

Are there non-stop flights from Chicago Midway to Oakland?

Route itineraries vary, offering both non-stop and connecting flight options depending on the airline and travel date.

Can I book my Chicago to Oakland flight by phone?

Yes, you can call Globitude Travels directly to speak with a travel agent, compare live fares, and complete your reservation over the phone.

Related routes

Chicago to Atlanta Chicago to Cancún Chicago to Charlotte Chicago to Denver Chicago to Fort Lauderdale Chicago to Fort Myers Dallas to Oakland Everett to Oakland Honolulu, Oahu to Oakland Little Rock to Oakland Los Angeles to Oakland Ontario to Oakland All routes →

Why book with Globitude Travels

💸 Transparent pricing
The fare you see is all-inclusive — taxes and fees shown before you pay, never after.

🤝 Real travel experts
Every booking is reviewed by our team, and phone-only vendor deals can beat any online price.

🎧 24/7 human support
Before, during and after your trip — changes, cancellations and special requests handled by people.

🔒 Secure checkout
Encrypted payment, verified confirmation emails, and your PNR delivered as soon as the airline issues it.

Globitude Travels is an independent travel agency — call 1-856-513-6369 or use the search above to compare live fares on this route. See our terms, privacy policy, refund policy and service fees for full details, or contact us any time.

Page updated August 14, 2026 · fare data refreshed automatically from live flight searches.