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Oakland (OAK) to Chicago (MDW) Flights from ₹15,869

Fares on this route currently start from ₹15,869. Compare live OAK to MDW prices, non-stop and connecting flights, departure times and airline choices before booking. Use the search panel to change origin, destination, passengers, cabin and trip type instantly.
OAK → MDW Approx. 2960.86 km 14 Jul 2026 Live inventory
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Showing 25 of 199 live flights
Southwest Airlines
WN-3059
23:55
07/14/2026
OAK
Metropolitan Oakland International Airport
6h 5m
Non-stop
06:00
07/15/2026
+1
MDW
Chicago Midway International Airport
₹15,869
per person
✕ Non-refundable14 fare options
Southwest Airlines
WN-3886
22:55
07/14/2026
SJC
Metropolitan Oakland International Airport
6h 5m
Non-stop
05:00
07/15/2026
+1
MDW
Chicago Midway International Airport
₹16,441
per person
✕ Non-refundable13 fare options
Southwest Airlines
WN-3901
05:15
07/14/2026
SFO
Metropolitan Oakland International Airport
6h 10m
Non-stop
11:25
07/14/2026
MDW
Chicago Midway International Airport
₹16,441
per person
✕ Non-refundable13 fare options
Southwest Airlines
WN-3649
23:40
07/14/2026
SFO
Metropolitan Oakland International Airport
6h 15m
Non-stop
05:55
07/15/2026
+1
MDW
Chicago Midway International Airport
₹16,441
per person
✕ Non-refundable13 fare options
Delta Air Lines
DL-1254
13:40
07/14/2026
SJC
Metropolitan Oakland International Airport
7h 49m
1 Stop
⏱ SLC · 0h 48mSLC Airport
21:29
07/14/2026
ORD
Chicago Midway International Airport
₹16,453
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-4026
09:45
07/14/2026
SJC
Metropolitan Oakland International Airport
9h 12m
1 Stop
⏱ SLC · 1h 59mSLC Airport
18:57
07/14/2026
ORD
Chicago Midway International Airport
₹16,453
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-2789
00:35
07/14/2026
SFO
Metropolitan Oakland International Airport
8h 2m
1 Stop
⏱ MSP · 0h 46mMSP Airport
08:37
07/14/2026
MDW
Chicago Midway International Airport
₹16,453
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-849
13:20
07/14/2026
SFO
Metropolitan Oakland International Airport
8h 9m
1 Stop
⏱ SLC · 1h 7mSLC Airport
21:29
07/14/2026
ORD
Chicago Midway International Airport
₹16,453
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-920
09:55
07/14/2026
SFO
Metropolitan Oakland International Airport
9h 2m
1 Stop
⏱ SLC · 1h 56mSLC Airport
18:57
07/14/2026
ORD
Chicago Midway International Airport
₹16,453
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-3842
14:59
07/14/2026
SJC
Metropolitan Oakland International Airport
8h 19m
1 Stop
⏱ LAX · 0h 51mLAX Airport
23:18
07/14/2026
ORD
Chicago Midway International Airport
₹16,453
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-2156
06:20
07/14/2026
SJC
Metropolitan Oakland International Airport
8h 45m
1 Stop
⏱ MSP · 1h 26mMSP Airport
15:05
07/14/2026
ORD
Chicago Midway International Airport
₹16,453
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-4041
07:20
07/14/2026
SJC
Metropolitan Oakland International Airport
9h 23m
1 Stop
⏱ SEA · 0h 53mSEA Airport
16:43
07/14/2026
ORD
Chicago Midway International Airport
₹16,453
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-4134
12:30
07/14/2026
OAK
Metropolitan Oakland International Airport
8h 59m
1 Stop
⏱ SLC · 1h 59mSLC Airport
21:29
07/14/2026
ORD
Chicago Midway International Airport
₹16,738
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-3937
19:10
07/14/2026
SJC
Metropolitan Oakland International Airport
12h 49m
2 Stops
⏱ SLC · 1h 44mSLC Airport⏱ DTW · 2h 18mDTW Airport
07:59
07/15/2026
+1
ORD
Chicago Midway International Airport
₹16,954
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-2418
20:35
07/14/2026
OAK
Metropolitan Oakland International Airport
8h 45m
1 Stop
⏱ PDX · 1h 20mPDX Airport
05:20
07/15/2026
+1
MDW
Chicago Midway International Airport
₹16,978
per person
✕ Non-refundable9 fare options
Southwest Airlines
WN-2938
05:30
07/14/2026
OAK
Metropolitan Oakland International Airport
7h 55m
1 Stop
⏱ LAS · 0h 50mLAS Airport
13:25
07/14/2026
MDW
Chicago Midway International Airport
₹16,978
per person
✕ Non-refundable🔥 Last 4 seats6 fare options
Southwest Airlines
WN-4693
13:10
07/14/2026
OAK
Metropolitan Oakland International Airport
8h 10m
1 Stop
⏱ LAS · 0h 55mLAS Airport
21:20
07/14/2026
MDW
Chicago Midway International Airport
₹16,978
per person
✕ Non-refundable6 fare options
Southwest Airlines
WN-4693
13:10
07/14/2026
OAK
Metropolitan Oakland International Airport
10h 35m
1 Stop
⏱ LAS · 3h 20mLAS Airport
23:45
07/14/2026
MDW
Chicago Midway International Airport
₹16,978
per person
✕ Non-refundable6 fare options
Southwest Airlines
WN-878
15:55
07/14/2026
OAK
Metropolitan Oakland International Airport
8h 15m
1 Stop
⏱ PHX · 0h 55mPHX Airport
00:10
07/15/2026
+1
MDW
Chicago Midway International Airport
₹16,978
per person
✕ Non-refundable6 fare options
Southwest Airlines
WN-3066
05:15
07/14/2026
OAK
Metropolitan Oakland International Airport
10h 25m
1 Stop
⏱ PHX · 3h 15mPHX Airport
15:40
07/14/2026
MDW
Chicago Midway International Airport
₹16,978
per person
✕ Non-refundable6 fare options
Southwest Airlines
WN-4279
14:50
07/14/2026
OAK
Metropolitan Oakland International Airport
9h 5m
1 Stop
⏱ HOU · 0h 50mHOU Airport
23:55
07/14/2026
MDW
Chicago Midway International Airport
₹16,978
per person
✕ Non-refundable🔥 Last 3 seats6 fare options
Southwest Airlines
WN-2601
19:30
07/14/2026
OAK
Metropolitan Oakland International Airport
9h 10m
1 Stop
⏱ SAN · 1h 35mSAN Airport
04:40
07/15/2026
+1
MDW
Chicago Midway International Airport
₹16,978
per person
✕ Non-refundable6 fare options
Southwest Airlines
WN-4978
12:10
07/14/2026
OAK
Metropolitan Oakland International Airport
10h 50m
1 Stop
⏱ LAX · 3h 25mLAX Airport
23:00
07/14/2026
MDW
Chicago Midway International Airport
₹16,978
per person
✕ Non-refundable6 fare options
Delta Air Lines
DL-4061
06:00
07/14/2026
OAK
Metropolitan Oakland International Airport
12h 18m
2 Stops
⏱ SLC · 2h 15mSLC Airport⏱ MSP · 2h 0mMSP Airport
18:18
07/14/2026
MDW
Chicago Midway International Airport
₹17,411
per person
✕ Non-refundable
Southwest Airlines
WN-3066
05:15
07/14/2026
OAK
Metropolitan Oakland International Airport
9h 20m
1 Stop
⏱ PHX · 0h 50mPHX Airport
14:35
07/14/2026
MDW
Chicago Midway International Airport
₹17,484
per person
✕ Non-refundable4 fare options
😕 No flights match your filters.
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,USA2960.86 km

📅 Results on this page are loaded for 14 Jul 2026. Click Load more flights to expand the full list on this page.

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

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More flights from Oakland (OAK)
31 routes
More flights from Chicago (MDW)
64 routes
Chicago Albany
MDW → ALB
Chicago Albuquerque
MDW → ABQ
Chicago Atlanta
MDW → ATL
Chicago Austin
MDW → AUS
Chicago Birmingham
MDW → BHM
Chicago Boston
MDW → BOS
Chicago Buffalo
MDW → BUF
Chicago Cancun
MDW → CUN
Chicago Charleston
MDW → CHS
Chicago Charlotte
MDW → CLT
Chicago Cleveland
MDW → CLE
Chicago Columbus
MDW → CMH
Chicago Denver
MDW → DEN
Chicago Des Moines
MDW → DSM
Chicago Detroit
MDW → DTW
Chicago Fort Lauderdale
MDW → FLL
Chicago Fort Myers
MDW → RSW
Chicago Greenville
MDW → GSP
Chicago Guadalajara
MDW → GDL
Chicago Hartford
MDW → BDL
Chicago Houston
MDW → HOU
Chicago Jackson
MDW → JAN
Chicago Jacksonville
MDW → JAX
Chicago Kansas City
MDW → MCI
Chicago Las Vegas
MDW → LAS
Chicago Little Rock
MDW → LIT
Chicago Los Angeles
MDW → LAX
Chicago Louisville
MDW → SDF
Chicago Manchester
MDW → MHT
Chicago Memphis
MDW → MEM
Chicago Minneapolis
MDW → MSP
Chicago Montego Bay
MDW → MBJ
Chicago Nashville
MDW → BNA
Chicago New Orleans
MDW → MSY
Chicago New York
MDW → LGA
Chicago Norfolk
MDW → ORF
Chicago Oakland
MDW → OAK
Chicago Oklahoma City
MDW → OKC
Chicago Omaha
MDW → OMA
Chicago Ontario
MDW → ONT
Chicago Orlando
MDW → MCO
Chicago Philadelphia
MDW → PHL
Chicago Phoenix
MDW → PHX
Chicago Pittsburgh International Airport
MDW → PIT
Chicago Portland International
MDW → PDX
Chicago Providence
MDW → PVD
Chicago Punta Cana
MDW → PUJ
Chicago Raleigh
MDW → RDU
Chicago Reno
MDW → RNO
Chicago Rochester
MDW → ROC
Chicago Sacramento
MDW → SMF
Chicago Salt Lake City
MDW → SLC
Chicago San Antonio
MDW → SAT
Chicago San Diego
MDW → SAN
Chicago San Francisco
MDW → SFO
Chicago San Jose
MDW → SJC
Chicago Seattle
MDW → SEA
Chicago St. Louis
MDW → STL
Chicago Tampa
MDW → TPA
Chicago Toronto
MDW → YTZ
Chicago Tucson
MDW → TUS
Chicago Tulsa
MDW → TUL
Chicago Washington DC
MDW → IAD
Chicago Wichita
MDW → ICT
❓ Frequently asked questions — Oakland to Chicago 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 Oakland,USA (OAK) and Chicago,USA (MDW) 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.