Compare live prices for MDW to OAK on
Fri, 08 May 2026. Use the search panel
to change origin, destination, passengers, cabin and trip type instantly.
MDW → OAKApprox. 2960.86 km08 May 2026Live inventory
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Showing 25
of 122
live flights
Delta Air Lines
DL-4688
13:22
05/08/2026
MDW
Chicago Midway International Airport
10h 35m
2 Stops
⏱ DTW · 2h 8mDTW Airport⏱ SLC · 3h 23mSLC Airport
23:57
05/08/2026
OAK
Metropolitan Oakland International Airport
₹13,931
per person
✕ Non-refundable
Southwest Airlines
WN-1748
21:50
05/08/2026
MDW
Chicago Midway International Airport
2h 35m
Non-stop
00:25
05/09/2026
+1
OAK
Metropolitan Oakland International Airport
₹16,675
per person
✕ Non-refundable6 fare options
Southwest Airlines
WN-3917
10:10
05/08/2026
MDW
Chicago Midway International Airport
2h 35m
Non-stop
12:45
05/08/2026
SFO
Metropolitan Oakland International Airport
₹17,225
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-1786
21:45
05/08/2026
MDW
Chicago Midway International Airport
2h 35m
Non-stop
00:20
05/09/2026
+1
SFO
Metropolitan Oakland International Airport
₹17,225
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-3813
06:24
05/08/2026
ORD
Chicago Midway International Airport
4h 53m
1 Stop
⏱ MSP · 0h 58mMSP Airport
11:17
05/08/2026
SFO
Metropolitan Oakland International Airport
₹17,235
per person
✕ Non-refundable
Delta Air Lines
DL-4716
19:13
05/08/2026
MDW
Chicago Midway International Airport
4h 37m
1 Stop
⏱ MSP · 0h 50mMSP Airport
23:50
05/08/2026
SFO
Metropolitan Oakland International Airport
₹17,235
per person
✕ Non-refundable
Delta Air Lines
DL-3877
11:09
05/08/2026
ORD
Chicago Midway International Airport
6h 40m
1 Stop
⏱ DTW · 2h 25mDTW Airport
17:49
05/08/2026
SFO
Metropolitan Oakland International Airport
₹17,235
per person
✕ Non-refundable
Delta Air Lines
DL-4685
09:22
05/08/2026
MDW
Chicago Midway International Airport
4h 53m
1 Stop
⏱ DTW · 0h 45mDTW Airport
14:15
05/08/2026
SFO
Metropolitan Oakland International Airport
₹17,235
per person
✕ Non-refundable
Delta Air Lines
DL-2417
12:53
05/08/2026
MDW
Chicago Midway International Airport
6h 12m
1 Stop
⏱ ATL · 1h 5mATL Airport
19:05
05/08/2026
SFO
Metropolitan Oakland International Airport
₹17,235
per person
✕ Non-refundable
Southwest Airlines
WN-898
18:10
05/08/2026
MDW
Chicago Midway International Airport
4h 35m
1 Stop
⏱ LAX · 0h 50mLAX Airport
22:45
05/08/2026
OAK
Metropolitan Oakland International Airport
₹17,766
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-3242
11:00
05/08/2026
MDW
Chicago Midway International Airport
5h 40m
1 Stop
⏱ BUR · 1h 55mBUR Airport
16:40
05/08/2026
OAK
Metropolitan Oakland International Airport
₹17,766
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-1390
10:05
05/08/2026
MDW
Chicago Midway International Airport
5h 55m
1 Stop
⏱ LGB · 2h 15mLGB Airport
16:00
05/08/2026
OAK
Metropolitan Oakland International Airport
₹17,766
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-2046
19:40
05/08/2026
MDW
Chicago Midway International Airport
4h 25m
1 Stop
⏱ PHX · 0h 45mPHX Airport
00:05
05/09/2026
+1
OAK
Metropolitan Oakland International Airport
₹17,766
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-2677
15:40
05/08/2026
MDW
Chicago Midway International Airport
5h 5m
1 Stop
⏱ LAS · 1h 35mLAS Airport
20:45
05/08/2026
OAK
Metropolitan Oakland International Airport
₹17,766
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-2677
15:40
05/08/2026
MDW
Chicago Midway International Airport
4h 20m
1 Stop
⏱ LAS · 0h 50mLAS Airport
20:00
05/08/2026
OAK
Metropolitan Oakland International Airport
₹17,766
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-2677
15:40
05/08/2026
MDW
Chicago Midway International Airport
7h 0m
1 Stop
⏱ LAS · 3h 35mLAS Airport
22:40
05/08/2026
OAK
Metropolitan Oakland International Airport
₹17,766
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-3340
05:25
05/08/2026
MDW
Chicago Midway International Airport
4h 55m
1 Stop
⏱ PHX · 0h 55mPHX Airport
10:20
05/08/2026
OAK
Metropolitan Oakland International Airport
₹17,766
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-3340
05:25
05/08/2026
MDW
Chicago Midway International Airport
6h 45m
1 Stop
⏱ PHX · 2h 55mPHX Airport
12:10
05/08/2026
OAK
Metropolitan Oakland International Airport
₹17,766
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-3541
17:25
05/08/2026
MDW
Chicago Midway International Airport
5h 5m
1 Stop
⏱ SAN · 1h 10mSAN Airport
22:30
05/08/2026
OAK
Metropolitan Oakland International Airport
₹17,766
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-3981
12:10
05/08/2026
MDW
Chicago Midway International Airport
5h 20m
1 Stop
⏱ LAS · 1h 50mLAS Airport
17:30
05/08/2026
OAK
Metropolitan Oakland International Airport
₹17,766
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-4631
06:55
05/08/2026
MDW
Chicago Midway International Airport
5h 15m
1 Stop
⏱ PHX · 1h 20mPHX Airport
12:10
05/08/2026
OAK
Metropolitan Oakland International Airport
₹17,766
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-4631
06:55
05/08/2026
MDW
Chicago Midway International Airport
7h 5m
1 Stop
⏱ PHX · 1h 45mPHX Airport
14:00
05/08/2026
OAK
Metropolitan Oakland International Airport
₹18,261
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-3340
05:25
05/08/2026
MDW
Chicago Midway International Airport
6h 10m
1 Stop
⏱ PHX · 0h 50mPHX Airport
11:35
05/08/2026
OAK
Metropolitan Oakland International Airport
₹18,261
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-2677
15:40
05/08/2026
MDW
Chicago Midway International Airport
7h 5m
1 Stop
⏱ LAS · 1h 55mLAS Airport
22:45
05/08/2026
OAK
Metropolitan Oakland International Airport
₹18,261
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-2677
15:40
05/08/2026
MDW
Chicago Midway International Airport
8h 15m
1 Stop
⏱ LAS · 4h 50mLAS Airport
23:55
05/08/2026
OAK
Metropolitan Oakland International Airport
₹18,290
per person
✕ Non-refundable4 fare options
😕 No flights match your filters.
Chicago (MDW)
📍 Chicago Midway International Airport
🌍 United States
🕐 GMT -6
📐 Latitude: 41.785999
📐 Longitude: -87.752403
Oakland (OAK)
📍 Metropolitan Oakland International Airport
🌍 United States
🕐 GMT -8
📐 Latitude: 37.721298
📐 Longitude: -122.221001
✈ Distance: Chicago,USA to Oakland,USA — 2960.86 km
📅 Results on this page are loaded for 08 May 2026. Click View all flights for the complete live search.
Chicago to Oakland — what to expect when booking
The MDW–OAK 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 Chicago,USA and Oakland,USA is approximately
2960.86 km.
Before you book
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❓ Frequently asked questions — Chicago to Oakland flights
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.
The straight-line distance between Chicago,USA (MDW) and Oakland,USA (OAK) is approximately 2960.86 km. Actual flying distance may vary slightly depending on routing.
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.
Mid-week departures often show lower prices than weekend travel on many routes. Use the date strip above to compare nearby days quickly.