Direct (non-stop) flights from Oakland (OAK) to Chicago (MDW)
Find comprehensive flight information, schedules, and booking details for direct flights from Oakland (OAK) to Chicago (MDW). 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)
Chicago (MDW)
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
Flight Schedule
December 2025
Airlines with direct flights from Oakland (OAK) to Chicago (MDW)
Route Insights
Pricing patterns: November typically offers lower prices due to reduced demand outside peak travel seasons.
Best departure times: Peak departure times are 5:00, offering more flight options and potentially better connections.
Oakland (OAK) - Chicago (MDW) flight price statistics
$574
ApproximateThe numbers are average prices found based on user searches for direct flights between the airports. It's calculated from the cheapest prices found per month for a round-trip with 1 adult and can vary depending on the amount of data we have for this particular route.
$609
Jan$503
Feb$1092
Mar$803
Apr$391
May$557
Jun$734
Jul$421
Aug$552
Sep$439
Oct$347
Nov$437
DecRelated Information
Airports: OAK • MDW Airport
Airlines operating this route: Southwest Airlines (WN)
Frequently Asked Questions
How many flights operate from OAK to MDW?
There is 1 direct flight operating from OAK to MDW. Approximately 1-2 flights daily.
Which airlines operate flights from OAK to MDW?
1 airline operates on this route: Southwest Airlines.
How long is the flight from OAK to MDW?
The flight duration from OAK to MDW is approximately 4h 00m - 4h 05m.
What is the distance from OAK to MDW?
The distance from OAK to 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 OAK to 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 OAK to 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 OAK to MDW?
The average flight price for a round-trip ticket from OAK to MDW is approximately $574 USD. Prices can vary based on booking time, season, and airline.
When is the best time to book flights from OAK to MDW for the lowest prices?
November is typically the cheapest month to fly from OAK to MDW. Booking in advance and avoiding peak travel seasons can help you find better deals.
How far is MDW from OAK?
The distance from OAK to MDW is 1850 miles (2977 km). This is a long-haul flight route.
How long does it take to fly from OAK to MDW?
The flight time from OAK to MDW is approximately 4h 00m - 4h 05m. Actual flight duration may vary based on weather conditions, aircraft type, and routing.