Direct (non-stop) flights from Chicago (MDW) to Oakland (OAK)
Find comprehensive flight information, schedules, and booking details for direct flights from Chicago (MDW), US to Oakland (OAK), US. This popular route is operated by 1 airline, offering multiple daily departures.• Flight Duration: 4h 30m - 4h 55m (average flight time)• Distance: 1850 miles (2977 km) (air miles between airports)• Daily Flights: 1-2 flights (scheduled departures per day)
Chicago (MDW)
US
Oakland (OAK)
US
FLIGHT TIME
4h 30m - 4h 55m
FLIGHT DISTANCE
1850 miles (2977 km)
4h 45m - 4h 45m
07:50
07:50
1850 miles (2977 km)
September
1 (Show)
7
Terminal 1 (Chicago (MDW))
Terminal 1 (Oakland (OAK))
Flight Schedule
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Airlines Operating This Route
Click any airline to view their specific flight schedules, policies, and route details for this connection. You can also explore flights from Chicago (MDW) and flights to Oakland (OAK).
Route Insights
Route Demand
This route operates 7 flights per week, serving moderate demand between Chicago (MDW) and Oakland (OAK).
Best Time to Fly
Best Value Period
September typically offers the best value for travelers, with lower average fares compared to peak travel periods.
Price Trends
Price variation throughout the year is significant, with Sep being the most affordable month and prices increasing during peak travel seasons.
Distance & Duration Explained
Route Distance
At 1850 miles (2977 km), this is an ultra-long-haul route between Chicago (MDW) and Oakland (OAK), requiring larger aircraft and extended flight times.
Flight Duration
Flight duration averages 4h 30m - 4h 55m, with actual times ranging from 4h 45m - 4h 45m depending on aircraft type, wind conditions, and routing.
Airline Comparison
Available Airlines
Southwest Airlines is the sole operator on this route, providing 1 daily flight between MDW and OAK.
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Best Time to Visit & Travel Planning
Cheapest Day
Cheapest Month
Average Fare
$327
Travel Planning Tips for Chicago (MDW) to Oakland (OAK)
- Best Day to Book
Wednesday typically offers the lowest fares for flights from Chicago (MDW) to Oakland (OAK). Consider booking on this day for potential savings.
- Best Month to Travel
May is generally the cheapest month to fly from Chicago (MDW) to Oakland (OAK). Plan your trip during this month for the best deals.
- Average Flight Price
The average fare for flights from Chicago (MDW) to Oakland (OAK) is approximately $327. Prices may vary based on booking time, season, and airline.
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Related Pages
Related Airports
Related Airlines
Frequently Asked Questions
How many flights operate from Chicago (MDW) to Oakland (OAK)?
There is 1 direct flight operating from Chicago (MDW) to Oakland (OAK). Approximately 1-2 flights daily.
Which airlines operate flights from Chicago (MDW) to Oakland (OAK)?
1 airline operates on this route: Southwest Airlines.
How long is the flight from Chicago (MDW) to Oakland (OAK)?
The flight duration from Chicago (MDW) to Oakland (OAK) is approximately 4h 30m - 4h 55m.
What is the distance from Chicago (MDW) to Oakland (OAK)?
The distance from Chicago (MDW) to Oakland (OAK) is 1850 miles (2977 km).
What is the flight time range for this route?
Flight times on this route range from 4h 45m - 4h 45m.
What are the earliest and latest flight departure times?
The earliest flight departs at 07:50 and the latest flight departs at 07:50.
What is the cheapest month to fly from Chicago (MDW) to Oakland (OAK)?
September is typically the cheapest month to fly on this route.
How many flights operate per week on this route?
Approximately 7 flights operate per week from Chicago (MDW) to Oakland (OAK).
What types of aircraft operate on this route?
This route is served by Boeing 737MAX 8 Passenger.
What is the average flight price from Chicago (MDW) to Oakland (OAK)?
The average flight price for a round-trip ticket from Chicago (MDW) to Oakland (OAK) is approximately $514 USD. Prices can vary based on booking time, season, and airline.
When is the best time to book flights from Chicago (MDW) to Oakland (OAK) for the lowest prices?
September is typically the cheapest month to fly from Chicago (MDW) to Oakland (OAK). Booking in advance and avoiding peak travel seasons can help you find better deals.
How far is Oakland (OAK) from Chicago (MDW)?
The distance from Chicago (MDW) to Oakland (OAK) is 1850 miles (2977 km). This is a long-haul flight route.
How long does it take to fly from Chicago (MDW) to Oakland (OAK)?
The flight time from Chicago (MDW) to Oakland (OAK) is approximately 4h 30m - 4h 55m. Actual flight duration may vary based on weather conditions, aircraft type, and routing.
What city does Oakland (OAK) serve?
Oakland (OAK) serves Oakland, US.