Delta Air Lines
DL-4134
12:34
04/15/2026
OAK
8h 44m
1 Stop
⏱ SLC · 1h 41m
21:18
04/15/2026
ORD
₹11,020
per person
Delta Air Lines
DL-4061
05:55
04/15/2026
OAK
10h 23m
2 Stops
⏱ SLC · 1h 3m⏱ DTW · 0h 30m
16:18
04/15/2026
ORD
₹11,514
per person
Delta Airlines
DL-4061
05:55
04/15/2026
OAK
12h 3m
2 Stops
⏱ SLC · 1h 3m⏱ DTW · 2h 20m
17:58
04/15/2026
MDW
₹11,572
per person
Southwest Airlines
WN-3551
05:50
04/15/2026
OAK
6h 5m
Non-stop
11:55
04/15/2026
MDW
₹13,028
per person
Southwest Airlines
WN-3552
23:55
04/15/2026
OAK
6h 5m
Non-stop
06:00
04/16/2026
+1
MDW
₹13,028
per person
Southwest Airlines Dallas
WN-3862
07:40
04/15/2026
OAK
9h 10m
1 Stop
⏱ HOU · 1h 0m
16:50
04/15/2026
MDW
₹14,125
per person
Southwest Airlines Dallas
WN-1087
20:50
04/15/2026
OAK
8h 50m
1 Stop
⏱ ONT · 1h 45m
05:40
04/16/2026
+1
MDW
₹14,125
per person
Southwest Airlines Dallas
WN-1536
08:15
04/15/2026
OAK
8h 45m
1 Stop
⏱ LGB · 1h 30m
17:00
04/15/2026
MDW
₹14,125
per person
Southwest Airlines Dallas
WN-3577
18:45
04/15/2026
OAK
9h 50m
1 Stop
⏱ SAN · 2h 25m
04:35
04/16/2026
+1
MDW
₹14,125
per person
Southwest Airlines Dallas
WN-3578
20:30
04/15/2026
OAK
8h 5m
1 Stop
⏱ SAN · 0h 40m
04:35
04/16/2026
+1
MDW
₹14,125
per person
Southwest Airlines Dallas
WN-3714
21:20
04/15/2026
OAK
8h 5m
1 Stop
⏱ LAS · 1h 0m
05:25
04/16/2026
+1
MDW
₹14,125
per person
Southwest Airlines Dallas
WN-186
15:00
04/15/2026
OAK
8h 20m
1 Stop
⏱ PHX · 1h 5m
23:20
04/15/2026
MDW
₹14,125
per person
Southwest Airlines Dallas
WN-1071
21:05
04/15/2026
OAK
7h 55m
1 Stop
⏱ PHX · 0h 55m
05:00
04/16/2026
+1
MDW
₹14,125
per person
Southwest Airlines Dallas
WN-3959
09:25
04/15/2026
OAK
7h 40m
1 Stop
⏱ DEN · 0h 50m
17:05
04/15/2026
MDW
₹14,125
per person
Southwest Airlines Dallas
WN-1063
06:35
04/15/2026
OAK
7h 40m
1 Stop
⏱ DEN · 0h 50m
14:15
04/15/2026
MDW
₹14,125
per person
Southwest Airlines
WN-1063
06:35
04/15/2026
OAK
10h 30m
1 Stop
⏱ DEN · 3h 35m
17:05
04/15/2026
MDW
₹14,125
per person
Southwest Airlines Dallas
WN-1063
06:35
04/15/2026
OAK
10h 5m
1 Stop
⏱ DEN · 1h 40m
16:40
04/15/2026
MDW
₹14,624
per person
Southwest Airlines Dallas
WN-556
10:45
04/15/2026
OAK
10h 15m
1 Stop
⏱ PHX · 1h 45m
21:00
04/15/2026
MDW
₹14,624
per person
Southwest Airlines Dallas
WN-278
17:45
04/15/2026
OAK
11h 15m
1 Stop
⏱ PHX · 4h 10m
05:00
04/16/2026
+1
MDW
₹14,652
per person
Southwest Airlines
WN-3862
07:40
04/15/2026
OAK
12h 55m
1 Stop
⏱ HOU · 4h 45m
20:35
04/15/2026
MDW
₹14,652
per person
Southwest Airlines
WN-540
15:45
04/15/2026
OAK
14h 0m
2 Stops
⏱ ONT · 2h 50m⏱ SMF · 2h 35m
05:45
04/16/2026
+1
MDW
₹14,799
per person
Southwest Airlines
WN-979
09:55
04/15/2026
OAK
11h 5m
2 Stops
⏱ BUR · 1h 50m⏱ PHX · 1h 5m
21:00
04/15/2026
MDW
₹14,799
per person
Southwest Airlines
WN-3959
09:25
04/15/2026
OAK
12h 20m
2 Stops
⏱ DEN · 1h 0m⏱ DAL · 2h 45m
21:45
04/15/2026
MDW
₹14,799
per person
Southwest Airlines
WN-3959
09:25
04/15/2026
OAK
10h 55m
2 Stops
⏱ DEN · 1h 0m⏱ DAL · 1h 15m
20:20
04/15/2026
MDW
₹14,799
per person
Southwest Airlines
WN-3959
09:25
04/15/2026
OAK
12h 20m
2 Stops
⏱ DEN · 3h 0m⏱ DAL · 0h 45m
21:45
04/15/2026
MDW
₹14,799
per person
😕 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,USA — 2960.86 km
📅 Results on this page are loaded for 15 Apr 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 Oakland (OAK)
33 routes
Oakland → Albuquerque
OAK → ABQ
Oakland → Austin
OAK → AUS
Oakland → Bellingham
OAK → BLI
Oakland → Boise
OAK → BOI
Oakland → Burbank
OAK → BUR
Oakland → Columbus
OAK → CMH
Oakland → Denver
OAK → DEN
Oakland → Eugene
OAK → EUG
Oakland → Fort Worth
OAK → DFW
Oakland → Guadalajara
OAK → GDL
Oakland → Honolulu
OAK → HNL
Oakland → Houston
OAK → HOU
Oakland → Kahului
OAK → OGG
Oakland → Kansas City
OAK → MCI
Oakland → Kona
OAK → KOA
Oakland → Las Vegas
OAK → LAS
Oakland → Lihue
OAK → LIH
Oakland → Long Beach
OAK → LGB
Oakland → Los Angeles
OAK → LAX
Oakland → Minneapolis
OAK → MSP
Oakland → New York
OAK → JFK
Oakland → Oklahoma City
OAK → OKC
Oakland → Ontario
OAK → ONT
Oakland → Phoenix
OAK → PHX
Oakland → Phoenix-Mesa Gateway
OAK → AZA
Oakland → Portland International
OAK → PDX
Oakland → Provo
OAK → PVU
Oakland → Salt Lake City
OAK → SLC
Oakland → San Diego
OAK → SAN
Oakland → Santa Ana
OAK → SNA
Oakland → Seattle
OAK → SEA
Oakland → Spokane
OAK → GEG
Oakland → Stockholm
OAK → ARN
More flights from Chicago (MDW)
69 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
