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Showing 25
of 142
live flights
23:59
05/11/2026
SFO
Metropolitan Oakland International Airport
8h 44m
1 Stop
⏱ DTW · 0h 52m DTW Airport
08:43
05/12/2026
+1
MDW
Chicago Midway International Airport
₹11,400
per person
Select →
✕ Non-refundable
23:59
05/11/2026
SFO
Metropolitan Oakland International Airport
8h 46m
1 Stop
⏱ DTW · 0h 42m DTW Airport
08:45
05/12/2026
+1
ORD
Chicago Midway International Airport
₹11,400
per person
Select →
✕ Non-refundable
05:50
05/11/2026
SFO
Metropolitan Oakland International Airport
10h 39m
1 Stop
⏱ DTW · 2h 36m DTW Airport
16:29
05/11/2026
ORD
Chicago Midway International Airport
₹11,400
per person
Select →
✕ Non-refundable
22:55
05/11/2026
SFO
Metropolitan Oakland International Airport
9h 44m
1 Stop
⏱ ATL · 0h 55m ATL Airport
08:39
05/12/2026
+1
ORD
Chicago Midway International Airport
₹11,400
per person
Select →
✕ Non-refundable
13:45
05/11/2026
SFO
Metropolitan Oakland International Airport
10h 14m
1 Stop
⏱ ATL · 1h 6m ATL Airport
23:59
05/11/2026
ORD
Chicago Midway International Airport
₹11,400
per person
Select →
✕ Non-refundable
Southwest Airlines
WN-3552
23:55
05/11/2026
OAK
Metropolitan Oakland International Airport
06:00
05/12/2026
+1
MDW
Chicago Midway International Airport
₹12,661
per person
Select →
✕ Non-refundable 6 fare options
Southwest Airlines
WN-4252
22:55
05/11/2026
SJC
Metropolitan Oakland International Airport
05:00
05/12/2026
+1
MDW
Chicago Midway International Airport
₹13,253
per person
Select →
✕ Non-refundable 5 fare options
Southwest Airlines
WN-2318
05:15
05/11/2026
SFO
Metropolitan Oakland International Airport
11:25
05/11/2026
MDW
Chicago Midway International Airport
₹13,253
per person
Select →
✕ Non-refundable 5 fare options
Southwest Airlines
WN-4216
23:25
05/11/2026
SFO
Metropolitan Oakland International Airport
05:40
05/12/2026
+1
MDW
Chicago Midway International Airport
₹13,253
per person
Select →
✕ Non-refundable 5 fare options
13:40
05/11/2026
SJC
Metropolitan Oakland International Airport
8h 10m
1 Stop
⏱ SLC · 1h 5m SLC Airport
21:50
05/11/2026
ORD
Chicago Midway International Airport
₹13,270
per person
Select →
✕ Non-refundable
09:40
05/11/2026
SJC
Metropolitan Oakland International Airport
9h 10m
1 Stop
⏱ SLC · 2h 1m SLC Airport
18:50
05/11/2026
ORD
Chicago Midway International Airport
₹13,270
per person
Select →
✕ Non-refundable
14:51
05/11/2026
SJC
Metropolitan Oakland International Airport
9h 6m
1 Stop
⏱ SEA · 0h 31m SEA Airport
23:57
05/11/2026
ORD
Chicago Midway International Airport
₹13,270
per person
Select →
✕ Non-refundable
07:36
05/11/2026
SJC
Metropolitan Oakland International Airport
9h 13m
1 Stop
⏱ SEA · 0h 30m SEA Airport
16:49
05/11/2026
ORD
Chicago Midway International Airport
₹13,270
per person
Select →
✕ Non-refundable
09:43
05/11/2026
SFO
Metropolitan Oakland International Airport
9h 7m
1 Stop
⏱ SLC · 1h 50m SLC Airport
18:50
05/11/2026
ORD
Chicago Midway International Airport
₹13,270
per person
Select →
✕ Non-refundable
Southwest Airlines
WN-1833
09:50
05/11/2026
OAK
Metropolitan Oakland International Airport
8h 10m
1 Stop
⏱ SLC · 1h 25m SLC Airport
18:00
05/11/2026
MDW
Chicago Midway International Airport
₹13,759
per person
Select →
✕ Non-refundable 🔥 Last 3 seats 4 fare options
Southwest Airlines
WN-3530
17:30
05/11/2026
OAK
Metropolitan Oakland International Airport
11h 30m
2 Stops
⏱ BUR · 1h 20m BUR Airport ⏱ SJC · 1h 45m SJC Airport
05:00
05/12/2026
+1
MDW
Chicago Midway International Airport
₹14,433
per person
Select →
✕ Non-refundable 4 fare options
Southwest Airlines
WN-1056
15:45
05/11/2026
OAK
Metropolitan Oakland International Airport
8h 10m
1 Stop
⏱ PHX · 0h 50m PHX Airport
23:55
05/11/2026
ORD
Chicago Midway International Airport
₹15,133
per person
Select →
✓ Refundable 🔥 Last 2 seats 4 fare options
Southwest Airlines
WN-3536
05:20
05/11/2026
OAK
Metropolitan Oakland International Airport
8h 35m
1 Stop
⏱ LAS · 1h 20m LAS Airport
13:55
05/11/2026
ORD
Chicago Midway International Airport
₹15,133
per person
Select →
✓ Refundable 4 fare options
Southwest Airlines
WN-2063
13:50
05/11/2026
OAK
Metropolitan Oakland International Airport
9h 5m
1 Stop
⏱ LAS · 1h 45m LAS Airport
22:55
05/11/2026
ORD
Chicago Midway International Airport
₹15,133
per person
Select →
✓ Refundable 🔥 Last 5 seats 4 fare options
Southwest Airlines
WN-4107
19:30
05/11/2026
SJC
Metropolitan Oakland International Airport
9h 5m
1 Stop
⏱ SAN · 1h 50m SAN Airport
04:35
05/12/2026
+1
MDW
Chicago Midway International Airport
₹15,133
per person
Select →
✓ Refundable 4 fare options
Southwest Airlines
WN-321
05:25
05/11/2026
SFO
Metropolitan Oakland International Airport
9h 35m
1 Stop
⏱ DEN · 2h 25m DEN Airport
15:00
05/11/2026
ORD
Chicago Midway International Airport
₹15,133
per person
Select →
✓ Refundable 4 fare options
00:45
05/11/2026
SFO
Metropolitan Oakland International Airport
07:07
05/11/2026
ORD
Chicago Midway International Airport
₹17,015
per person
Select →
✕ Non-refundable 3 fare options
23:56
05/11/2026
SFO
Metropolitan Oakland International Airport
06:20
05/12/2026
+1
ORD
Chicago Midway International Airport
₹17,015
per person
Select →
✕ Non-refundable 3 fare options
19:00
05/11/2026
SFO
Metropolitan Oakland International Airport
01:28
05/12/2026
+1
ORD
Chicago Midway International Airport
₹17,015
per person
Select →
✕ Non-refundable 3 fare options
18:29
05/11/2026
SFO
Metropolitan Oakland International Airport
00:59
05/12/2026
+1
ORD
Chicago Midway International Airport
₹17,015
per person
Select →
✕ Non-refundable 3 fare options
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Oakland (OAK)
📍 Metropolitan Oakland International Airport
🌍 United States
🕐 GMT -8
📐 Latitude: 37.721298
📐 Longitude: -122.221001
Chicago (MDW)
📍 Chicago Midway International Airport
🌍 United States
🕐 GMT -6
📐 Latitude: 41.785999
📐 Longitude: -87.752403
✈ Distance: Oakland,USA to Chicago,USA — 2960.86 km
📅 Results on this page are loaded for 11 May 2026 . Click View all flights for the complete live search.
Oakland to Chicago — what to expect when booking
The OAK–MDW route is served by multiple carriers throughout the year.
Fares on this route can move quickly — a price available now may not be there 30 minutes later.
If your dates are flexible, try shifting your departure by a day or two using the date strip above.
Mid-week departures often show lower base fares compared to weekend starts on many routes.
The distance between Oakland,USA and Chicago,USA is approximately
2960.86 km .
Before you book
Compare nearby dates The date strip above lets you scan nearby fares without restarting the search.
Open full search for more control Route page shows a limited live set. Full search opens the complete inventory with fresh results.
Check fare details Each result shows baggage, refundability and fare details before you proceed.
More flights from Oakland (OAK)
33 routes
More flights from Chicago (MDW)
69 routes
❓ Frequently asked questions — Oakland to Chicago flights
▼ Is it worth booking Oakland to Chicago flights in advance?
Generally yes — fares on most routes are most competitive around 4–6 weeks before departure. Booking earlier usually means better availability and a lower base fare when your dates are fixed.
▼ How far is Oakland from Chicago by air?
The straight-line distance between Oakland,USA (OAK) and Chicago,USA (MDW) is approximately 2960.86 km. Actual flying distance may vary slightly depending on routing.
▼ Are there non-stop flights from OAK to MDW?
Non-stop availability on this route varies by airline schedule and season. Use the filters below to quickly check whether direct options are available on your selected date.
▼ What is the cheapest day to fly from Oakland to Chicago?
Mid-week departures often show lower prices than weekend travel on many routes. Use the date strip above to compare nearby days quickly.