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Showing 25
of 196
live flights
17:05
05/11/2026
OAK
Metropolitan Oakland International Airport
16h 55m
2 Stops
⏱ SLC · 3h 36m SLC Airport ⏱ ATL · 3h 49m ATL Airport
10:00
05/12/2026
+1
MDW
Chicago Midway International Airport
₹11,557
per person
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✕ Non-refundable 2 fare options
18:55
05/11/2026
OAK
Metropolitan Oakland International Airport
18h 18m
1 Stop
⏱ SAN · 10h 39m SAN Airport
13:13
05/12/2026
+1
ORD
Chicago Midway International Airport
₹13,949
per person
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✕ Non-refundable 3 fare options
10:57
05/11/2026
OAK
Metropolitan Oakland International Airport
26h 16m
1 Stop
⏱ SAN · 18h 37m SAN Airport
13:13
05/12/2026
+1
ORD
Chicago Midway International Airport
₹16,862
per person
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✕ Non-refundable 3 fare options
15:18
05/11/2026
OAK
Metropolitan Oakland International Airport
21h 55m
1 Stop
⏱ SAN · 14h 16m SAN Airport
13:13
05/12/2026
+1
ORD
Chicago Midway International Airport
₹16,862
per person
Select →
✕ Non-refundable 3 fare options
10:57
05/11/2026
OAK
Metropolitan Oakland International Airport
12h 46m
1 Stop
⏱ SAN · 5h 10m SAN Airport
23:43
05/11/2026
ORD
Chicago Midway International Airport
₹17,370
per person
Select →
✕ Non-refundable 3 fare options
06:41
05/11/2026
OAK
Metropolitan Oakland International Airport
12h 22m
1 Stop
⏱ SAN · 4h 43m SAN Airport
19:03
05/11/2026
ORD
Chicago Midway International Airport
₹17,370
per person
Select →
✕ Non-refundable 3 fare options
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
₹17,857
per person
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✕ Non-refundable 10 fare options
13:25
05/11/2026
SFO
Metropolitan Oakland International Airport
8h 25m
1 Stop
⏱ SLC · 1h 19m SLC Airport
21:50
05/11/2026
ORD
Chicago Midway International Airport
₹18,272
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
₹18,272
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
₹18,272
per person
Select →
✕ Non-refundable
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
₹18,272
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
₹18,272
per person
Select →
✕ Non-refundable
05:55
05/11/2026
SFO
Metropolitan Oakland International Airport
10h 54m
1 Stop
⏱ SEA · 2h 18m SEA Airport
16:49
05/11/2026
ORD
Chicago Midway International Airport
₹18,272
per person
Select →
✕ Non-refundable
18:55
05/11/2026
OAK
Metropolitan Oakland International Airport
24h 8m
1 Stop
⏱ SAN · 16h 29m SAN Airport
19:03
05/12/2026
+1
ORD
Chicago Midway International Airport
₹18,720
per person
Select →
✕ Non-refundable 3 fare options
Southwest Airlines
WN-3578
20:30
05/11/2026
OAK
Metropolitan Oakland International Airport
8h 5m
1 Stop
⏱ SAN · 0h 40m SAN Airport
04:35
05/12/2026
+1
MDW
Chicago Midway International Airport
₹18,954
per person
Select →
✕ Non-refundable 9 fare options
Southwest Airlines
WN-1071
20:55
05/11/2026
OAK
Metropolitan Oakland International Airport
8h 5m
1 Stop
⏱ PHX · 1h 0m PHX Airport
05:00
05/12/2026
+1
MDW
Chicago Midway International Airport
₹18,954
per person
Select →
✕ Non-refundable 9 fare options
Southwest Airlines
WN-3577
18:10
05/11/2026
OAK
Metropolitan Oakland International Airport
10h 25m
1 Stop
⏱ SAN · 3h 0m SAN Airport
04:35
05/12/2026
+1
MDW
Chicago Midway International Airport
₹18,954
per person
Select →
✕ Non-refundable 5 fare options
Southwest Airlines
WN-3559
20:55
05/11/2026
OAK
Metropolitan Oakland International Airport
8h 55m
1 Stop
⏱ PDX · 1h 15m PDX Airport
05:50
05/12/2026
+1
MDW
Chicago Midway International Airport
₹18,954
per person
Select →
✕ Non-refundable 5 fare options
Southwest Airlines
WN-1087
20:00
05/11/2026
OAK
Metropolitan Oakland International Airport
9h 40m
1 Stop
⏱ ONT · 2h 35m ONT Airport
05:40
05/12/2026
+1
MDW
Chicago Midway International Airport
₹18,954
per person
Select →
✕ Non-refundable 5 fare options
06:41
05/11/2026
OAK
Metropolitan Oakland International Airport
17h 2m
1 Stop
⏱ SAN · 9h 26m SAN Airport
23:43
05/11/2026
ORD
Chicago Midway International Airport
₹19,210
per person
Select →
✕ Non-refundable 3 fare options
Southwest Airlines
WN-278
17:15
05/11/2026
OAK
Metropolitan Oakland International Airport
11h 45m
1 Stop
⏱ PHX · 4h 40m PHX Airport
05:00
05/12/2026
+1
MDW
Chicago Midway International Airport
₹19,481
per person
Select →
✕ Non-refundable 5 fare options
Southwest Airlines
WN-540
16:00
05/11/2026
OAK
Metropolitan Oakland International Airport
13h 0m
2 Stops
⏱ ONT · 1h 30m ONT Airport ⏱ SJC · 2h 55m SJC Airport
05:00
05/12/2026
+1
MDW
Chicago Midway International Airport
₹19,628
per person
Select →
✕ Non-refundable 4 fare options
Southwest Airlines
WN-3807
17:45
05/11/2026
OAK
Metropolitan Oakland International Airport
13h 50m
2 Stops
⏱ LAX · 2h 40m LAX Airport ⏱ BWI · 0h 45m BWI Airport
07:35
05/12/2026
+1
MDW
Chicago Midway International Airport
₹19,628
per person
Select →
✕ Non-refundable 4 fare options
Southwest Airlines
WN-298
20:30
05/11/2026
OAK
Metropolitan Oakland International Airport
13h 5m
2 Stops
⏱ LAS · 1h 50m LAS Airport ⏱ HOU · 2h 20m HOU Airport
09:35
05/12/2026
+1
MDW
Chicago Midway International Airport
₹19,628
per person
Select →
✕ Non-refundable 4 fare options
Southwest Airlines
WN-2863
15:40
05/11/2026
OAK
Metropolitan Oakland International Airport
13h 20m
2 Stops
⏱ LAX · 2h 15m LAX Airport ⏱ SJC · 2h 25m SJC Airport
05:00
05/12/2026
+1
MDW
Chicago Midway International Airport
₹19,628
per person
Select →
✕ Non-refundable 4 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.