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 July 2026, Southwest Airlines was the only carrier flying nonstop MDW–OAK; the Boeing 737 MAX 8 was the most common aircraft at 66% of departures; flights ran 94% full.
Departures
115
July 2026
Seats
20,125
both directions
Passengers
18,897
both directions
Load factor
93.9%
RPM ÷ ASM
Who flies MDW–OAK?
Southwest Airlines was the only carrier to fly nonstop MDW–OAK in July 2026 (115 departures).
- WN
115 departures · 20,125 seats
Share of departures100.0%93.9%
Load
What plane flies MDW–OAK?
In July 2026, the Boeing 737 MAX 8 flew 66% of MDW–OAK departures — more than any other aircraft type.
- Boeing 737 MAX 8
76 departures · 94.5% load
66.1% - Boeing 737-800
39 departures · 92.6% load
33.9%
How has MDW–OAK traffic changed?
Nonstop MDW–OAK departures rose from 72 in August 2025 to 115 in July 2026.
Monthly nonstop MDW–OAK traffic, trailing 12 months through July 2026. Bars scale to the busiest month; months with no filed service show as zero.
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
June 2026
112 departures · 18,367 passengers
93.7%
Load
July 2026
115 departures · 18,897 passengers
93.9%
Load
By direction
Each direction is filed separately — they rarely match.
OAK → MDW
94.1% full
58 departures · 9,551 passengers
MDW → OAK
93.7% full
57 departures · 9,346 passengers
Nonstop MDW–OAK traffic has been filed since 2025.
Source: US DOT BTS Form 41 T-100 Segment (All Carriers). Data through July 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 July 2026, the Boeing 737 MAX 8 flew the largest share of departures (66.1%), followed by the Boeing 737-800 (33.9%).
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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