Direct (non-stop) flights from Oakland (OAK) to Chicago (MDW)
Find comprehensive flight information, schedules, and booking details for direct flights from Oakland (OAK), US to Chicago (MDW), US. This popular route is operated by 1 airline, offering multiple daily departures.• Flight Duration: 4h 00m - 4h 05m (average flight time)• Distance: 1850 miles (2977 km) (air miles between airports)• Daily Flights: 1-2 flights (scheduled departures per day)
Oakland (OAK)
US
Chicago (MDW)
US
FLIGHT TIME
4h 00m - 4h 05m
FLIGHT DISTANCE
1850 miles (2977 km)
4h 5m - 4h 5m
05:25
05:25
1850 miles (2977 km)
November
1 (Show)
7
Terminal 1 (Oakland (OAK))
Terminal 1 (Chicago (MDW))
Flight Schedule
Loading calendar...
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 Oakland (OAK) and flights to Chicago (MDW).
Route Insights
Route Demand
This route operates 7 flights per week, serving moderate demand between Oakland (OAK) and Chicago (MDW).
Best Time to Fly
Best Value Period
November 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 Nov 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 Oakland (OAK) and Chicago (MDW), requiring larger aircraft and extended flight times.
Flight Duration
Flight duration averages 4h 00m - 4h 05m, with actual times ranging from 4h 5m - 4h 5m 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 OAK and MDW.
Loading weather charts...
Best Time to Visit & Travel Planning
Cheapest Day
Cheapest Month
Average Fare
$303
Travel Planning Tips for Oakland (OAK) to Chicago (MDW)
- Best Day to Book
Wednesday typically offers the lowest fares for flights from Oakland (OAK) to Chicago (MDW). Consider booking on this day for potential savings.
- Best Month to Travel
April is generally the cheapest month to fly from Oakland (OAK) to Chicago (MDW). Plan your trip during this month for the best deals.
- Average Flight Price
The average fare for flights from Oakland (OAK) to Chicago (MDW) is approximately $303. Prices may vary based on booking time, season, and airline.
Loading price statistics...
Related Pages
Related Airports
Related Airlines
Frequently Asked Questions
How many flights operate from Oakland (OAK) to Chicago (MDW)?
There is 1 direct flight operating from Oakland (OAK) to Chicago (MDW). Approximately 1-2 flights daily.
Which airlines operate flights from Oakland (OAK) to Chicago (MDW)?
1 airline operates on this route: Southwest Airlines.
How long is the flight from Oakland (OAK) to Chicago (MDW)?
The flight duration from Oakland (OAK) to Chicago (MDW) is approximately 4h 00m - 4h 05m.
What is the distance from Oakland (OAK) to Chicago (MDW)?
The distance from Oakland (OAK) to Chicago (MDW) is 1850 miles (2977 km).
What is the flight time range for this route?
Flight times on this route range from 4h 5m - 4h 5m.
What are the earliest and latest flight departure times?
The earliest flight departs at 05:25 and the latest flight departs at 05:25.
What is the cheapest month to fly from Oakland (OAK) to Chicago (MDW)?
November 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 Oakland (OAK) to Chicago (MDW).
What types of aircraft operate on this route?
This route is served by Boeing 737MAX 8 Passenger.
What is the average flight price from Oakland (OAK) to Chicago (MDW)?
The average flight price for a round-trip ticket from Oakland (OAK) to Chicago (MDW) is approximately $574 USD. Prices can vary based on booking time, season, and airline.
When is the best time to book flights from Oakland (OAK) to Chicago (MDW) for the lowest prices?
November is typically the cheapest month to fly from Oakland (OAK) to Chicago (MDW). Booking in advance and avoiding peak travel seasons can help you find better deals.
How far is Chicago (MDW) from Oakland (OAK)?
The distance from Oakland (OAK) to Chicago (MDW) is 1850 miles (2977 km). This is a long-haul flight route.
How long does it take to fly from Oakland (OAK) to Chicago (MDW)?
The flight time from Oakland (OAK) to Chicago (MDW) is approximately 4h 00m - 4h 05m. Actual flight duration may vary based on weather conditions, aircraft type, and routing.
What city does Chicago (MDW) serve?
Chicago (MDW) serves Chicago, US.