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Oakland to Chicago flight ticket price

Compare live prices for OAK to MDW. Use the search panel to change origin, destination, passengers, cabin and trip type instantly.
OAK → MDW Approx. 2960.86 km 11 May 2026 Live inventory
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Showing 25 of 142 live flights
Delta Air Lines
DL-335
23:59
05/11/2026
SFO
Metropolitan Oakland International Airport
8h 44m
1 Stop
⏱ DTW · 0h 52mDTW Airport
08:43
05/12/2026
+1
MDW
Chicago Midway International Airport
₹11,400
per person
✕ Non-refundable
Delta Air Lines
DL-335
23:59
05/11/2026
SFO
Metropolitan Oakland International Airport
8h 46m
1 Stop
⏱ DTW · 0h 42mDTW Airport
08:45
05/12/2026
+1
ORD
Chicago Midway International Airport
₹11,400
per person
✕ Non-refundable
Delta Air Lines
DL-772
05:50
05/11/2026
SFO
Metropolitan Oakland International Airport
10h 39m
1 Stop
⏱ DTW · 2h 36mDTW Airport
16:29
05/11/2026
ORD
Chicago Midway International Airport
₹11,400
per person
✕ Non-refundable
Delta Air Lines
DL-495
22:55
05/11/2026
SFO
Metropolitan Oakland International Airport
9h 44m
1 Stop
⏱ ATL · 0h 55mATL Airport
08:39
05/12/2026
+1
ORD
Chicago Midway International Airport
₹11,400
per person
✕ Non-refundable
Delta Air Lines
DL-531
13:45
05/11/2026
SFO
Metropolitan Oakland International Airport
10h 14m
1 Stop
⏱ ATL · 1h 6mATL Airport
23:59
05/11/2026
ORD
Chicago Midway International Airport
₹11,400
per person
✕ Non-refundable
Southwest Airlines
WN-3552
23:55
05/11/2026
OAK
Metropolitan Oakland International Airport
6h 5m
Non-stop
06:00
05/12/2026
+1
MDW
Chicago Midway International Airport
₹12,661
per person
✕ Non-refundable6 fare options
Southwest Airlines
WN-4252
22:55
05/11/2026
SJC
Metropolitan Oakland International Airport
6h 5m
Non-stop
05:00
05/12/2026
+1
MDW
Chicago Midway International Airport
₹13,253
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-2318
05:15
05/11/2026
SFO
Metropolitan Oakland International Airport
6h 10m
Non-stop
11:25
05/11/2026
MDW
Chicago Midway International Airport
₹13,253
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-4216
23:25
05/11/2026
SFO
Metropolitan Oakland International Airport
6h 15m
Non-stop
05:40
05/12/2026
+1
MDW
Chicago Midway International Airport
₹13,253
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-1254
13:40
05/11/2026
SJC
Metropolitan Oakland International Airport
8h 10m
1 Stop
⏱ SLC · 1h 5mSLC Airport
21:50
05/11/2026
ORD
Chicago Midway International Airport
₹13,270
per person
✕ Non-refundable
Delta Air Lines
DL-3982
09:40
05/11/2026
SJC
Metropolitan Oakland International Airport
9h 10m
1 Stop
⏱ SLC · 2h 1mSLC Airport
18:50
05/11/2026
ORD
Chicago Midway International Airport
₹13,270
per person
✕ Non-refundable
Delta Air Lines
DL-3789
14:51
05/11/2026
SJC
Metropolitan Oakland International Airport
9h 6m
1 Stop
⏱ SEA · 0h 31mSEA Airport
23:57
05/11/2026
ORD
Chicago Midway International Airport
₹13,270
per person
✕ Non-refundable
Delta Air Lines
DL-4041
07:36
05/11/2026
SJC
Metropolitan Oakland International Airport
9h 13m
1 Stop
⏱ SEA · 0h 30mSEA Airport
16:49
05/11/2026
ORD
Chicago Midway International Airport
₹13,270
per person
✕ Non-refundable
Delta Air Lines
DL-920
09:43
05/11/2026
SFO
Metropolitan Oakland International Airport
9h 7m
1 Stop
⏱ SLC · 1h 50mSLC Airport
18:50
05/11/2026
ORD
Chicago Midway International Airport
₹13,270
per person
✕ Non-refundable
Southwest Airlines
WN-1833
09:50
05/11/2026
OAK
Metropolitan Oakland International Airport
8h 10m
1 Stop
⏱ SLC · 1h 25mSLC Airport
18:00
05/11/2026
MDW
Chicago Midway International Airport
₹13,759
per person
✕ Non-refundable🔥 Last 3 seats4 fare options
Southwest Airlines
WN-3530
17:30
05/11/2026
OAK
Metropolitan Oakland International Airport
11h 30m
2 Stops
⏱ BUR · 1h 20mBUR Airport⏱ SJC · 1h 45mSJC Airport
05:00
05/12/2026
+1
MDW
Chicago Midway International Airport
₹14,433
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-1056
15:45
05/11/2026
OAK
Metropolitan Oakland International Airport
8h 10m
1 Stop
⏱ PHX · 0h 50mPHX Airport
23:55
05/11/2026
ORD
Chicago Midway International Airport
₹15,133
per person
✓ Refundable🔥 Last 2 seats4 fare options
Southwest Airlines
WN-3536
05:20
05/11/2026
OAK
Metropolitan Oakland International Airport
8h 35m
1 Stop
⏱ LAS · 1h 20mLAS Airport
13:55
05/11/2026
ORD
Chicago Midway International Airport
₹15,133
per person
✓ Refundable4 fare options
Southwest Airlines
WN-2063
13:50
05/11/2026
OAK
Metropolitan Oakland International Airport
9h 5m
1 Stop
⏱ LAS · 1h 45mLAS Airport
22:55
05/11/2026
ORD
Chicago Midway International Airport
₹15,133
per person
✓ Refundable🔥 Last 5 seats4 fare options
Southwest Airlines
WN-4107
19:30
05/11/2026
SJC
Metropolitan Oakland International Airport
9h 5m
1 Stop
⏱ SAN · 1h 50mSAN Airport
04:35
05/12/2026
+1
MDW
Chicago Midway International Airport
₹15,133
per person
✓ Refundable4 fare options
Southwest Airlines
WN-321
05:25
05/11/2026
SFO
Metropolitan Oakland International Airport
9h 35m
1 Stop
⏱ DEN · 2h 25mDEN Airport
15:00
05/11/2026
ORD
Chicago Midway International Airport
₹15,133
per person
✓ Refundable4 fare options
United Airlines
UA-1045
00:45
05/11/2026
SFO
Metropolitan Oakland International Airport
6h 22m
Non-stop
07:07
05/11/2026
ORD
Chicago Midway International Airport
₹17,015
per person
✕ Non-refundable3 fare options
United Airlines
UA-2056
23:56
05/11/2026
SFO
Metropolitan Oakland International Airport
6h 24m
Non-stop
06:20
05/12/2026
+1
ORD
Chicago Midway International Airport
₹17,015
per person
✕ Non-refundable3 fare options
United Airlines
UA-2019
19:00
05/11/2026
SFO
Metropolitan Oakland International Airport
6h 28m
Non-stop
01:28
05/12/2026
+1
ORD
Chicago Midway International Airport
₹17,015
per person
✕ Non-refundable3 fare options
United Airlines
UA-1230
18:29
05/11/2026
SFO
Metropolitan Oakland International Airport
6h 30m
Non-stop
00:59
05/12/2026
+1
ORD
Chicago Midway International Airport
₹17,015
per person
✕ Non-refundable3 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 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

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More flights from Oakland (OAK)
33 routes
More flights from Chicago (MDW)
69 routes
Chicago Albany
MDW → ALB
Chicago Albuquerque
MDW → ABQ
Chicago Amarillo
MDW → AMA
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 Leon
MDW → BJX
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 Morelia
MDW → MLM
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 Trenton
MDW → TTN
Chicago Tucson
MDW → TUS
Chicago Tulsa
MDW → TUL
Chicago Washington DC
MDW → IAD
Chicago Wichita
MDW → ICT
Chicago Zacatecas
MDW → ZCL
❓ 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.