Chicago (MDW) to Oakland (OAK)
Flight time
≈ 4h 29m
Bearing
273° W
Chicago (MDW) to Oakland (OAK) is 1,840 miles (2,961 km) as the crow flies — the great-circle baseline most distance-based mileage programs credit.
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What actually flies MDW–OAK
Filed traffic dataIn May 2026, Southwest Airlines was the only carrier flying nonstop MDW–OAK; the Boeing 737 MAX 8 was the most common aircraft at 69% of departures; flights ran 89% full.
Departures
104
May 2026
Seats
18,162
both directions
Passengers
16,196
both directions
Load factor
89.2%
RPM ÷ ASM
Who flies MDW–OAK?
Southwest Airlines was the only carrier to fly nonstop MDW–OAK in May 2026 (104 departures).
- WN
104 departures · 18,162 seats
Share of departures100.0%89.2%
Load
What plane flies MDW–OAK?
In May 2026, the Boeing 737 MAX 8 flew 69% of MDW–OAK departures — more than any other aircraft type.
- Boeing 737 MAX 8
72 departures · 89.2% load
69.2% - Boeing 737-800
31 departures · 89.1% load
29.8% - Boeing 737-700
1 departures · 92.7% load
1.0%
How has MDW–OAK traffic changed?
Nonstop MDW–OAK departures rose from 67 in June 2025 to 104 in May 2026.
Monthly nonstop MDW–OAK traffic, trailing 12 months through May 2026. Bars scale to the busiest month; months with no filed service show as zero.
June 2025
67 departures · 10,627 passengers
91.1%
Load
July 2025
68 departures · 11,153 passengers
93.7%
Load
August 2025
72 departures · 10,919 passengers
93.0%
Load
September 2025
68 departures · 9,937 passengers
90.8%
Load
October 2025
71 departures · 10,967 passengers
89.2%
Load
November 2025
63 departures · 9,130 passengers
85.3%
Load
December 2025
67 departures · 9,891 passengers
89.5%
Load
January 2026
64 departures · 8,034 passengers
77.5%
Load
February 2026
56 departures · 7,243 passengers
77.8%
Load
March 2026
103 departures · 14,874 passengers
84.1%
Load
April 2026
106 departures · 15,875 passengers
85.9%
Load
May 2026
104 departures · 16,196 passengers
89.2%
Load
By direction
Each direction is filed separately — they rarely match.
MDW → OAK
90.5% full
52 departures · 8,204 passengers
OAK → MDW
87.8% full
52 departures · 7,992 passengers
Nonstop MDW–OAK traffic has been filed since 2025.
Source: US DOT BTS Form 41 T-100 Segment (All Carriers). Data through May 2026; filings from 2025. Public domain (US Government work).
The airports
Oakland
US
San Francisco Bay Oakland International Airport
Coordinates
37.72°N, 122.22°W
Hemisphere
N · W
Frequently asked
How far is Chicago (MDW) from Oakland (OAK)?
MDW to OAK is 1,840 miles (2,961 km / 1,599 nautical miles) measured great-circle — the shortest path over the surface of the Earth.
How long is the flight from MDW to OAK?
A nonstop covers the 1,840-mile great-circle distance in roughly 4h 29m of block time, before winds. Actual schedules vary a few percent by direction and aircraft.
What plane flies MDW–OAK?
In May 2026, the Boeing 737 MAX 8 flew the largest share of departures (69.2%), followed by the Boeing 737-800 (29.8%).
What mileage do I earn flying MDW–OAK?
Distance-based programs credit off the 1,840-mile great-circle figure, then apply your fare-class earning rate. Revenue-based programs credit off the fare instead.
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