Oakland to Chicago (OAK–MDW) — Airlines, Schedules & Connections

OAK Airport Page →
1,840 mi airlines 12/wk
On-time Some delays Frequent delays
Flight Schedule 6 flights Verified 20m ago
Nonstop 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop
✓
→
WN3552
WN Southwest
73H
12:40 AM
PDT T2
6:26 AM
CDT
3h 46m
—
M T W T F S S
Prices
✓
→
WN3551
WN Southwest
738
5:55 AM
PDT T2
12:00 PM
CDT
4h 5m
—
M T W T F S S
Prices
✓
←
WN192
WN Southwest
B38M
10:00 AM
CDT
12:35 PM
PDT
4h 35m
—
M T W T F S S
Prices
✓
←
WN1743
WN Southwest
B38M
10:05 AM
CDT
12:40 PM
PDT
4h 35m
—
M T W T F S S
Prices
✓
←
WN186
WN Southwest
7S7
11:05 AM
CDT
1:40 PM
PDT
4h 35m
—
M T W T F S S
Prices
✓
←
WN1748
WN Southwest
7M8
9:50 PM
CDT
12:25 AM+1
PDT
4h 35m
—
M T W T F S S
Prices

No flights match your filters.

No nonstop flights on this route. connecting options below.

✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Oakland to Chicago
1 carrier, 12 flights/week nonstop.
1 Airlines 12 Flights/wk 1,840 mi 3h 46m nonstop +2h ahead 98 1-stop hubs

OAK–MDW is served by 1 airline with nonstop service. Southwest Airlines leads the route. The flight covers 1,840 miles in approximately 3h 46m. Beyond nonstop, 98 hubs offer 1-stop connections.

Also explore OAK Routes MDW Routes OAK Live Flights MDW Live Flights OAK Delays MDW Delays
Carriers on this route

Airline Landscape

All carriers operating nonstop OAK–MDW service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
WN Southwest Airlines 12 738, 73H 3h46-4h05 65% – –
Aircraft on this route
738 Boeing 737-800 – WN
73H Boeing 737-800 (Winglets) – WN
Alliance coverage
Unaffiliated: WN (12 flights/wk, 100%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.
Schedule

Weekly Schedule Pattern

Nonstop flight frequency by day of week, OAK to MDW direction.
Mon
2
flights
Tue
2
flights
Wed
2
flights
Thu
2
flights
Fri
2
flights
Sat
1
flight
Sun
1
flight
Departure time distribution
12 AM6 AM12 PM6 PM12 AM
Morning departures
Afternoon/evening departures
2
Nonstop flights
12
Outbound / wk
13
Return / wk
Connections

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for OAK to MDW.
1-STOP
One-Stop Connections
98
Hubs
~5h
Fastest
~22h
Longest
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
1,032
Candidates
Two-stop connections loaded in the connections tab above.
Connections computed from published schedules with minimum connection time verification. Use the interactive explorer above the fold to filter by airline, tier, and layover time.
Alternatives

Other ways to reach Chicago from Oakland

Nearby airports with service to Chicago Midway International Airport.
Metric OAK→MDW SFO→MDW SJC→MDW
Distance from OAK – 11 mi 29 mi
Nonstop airlines 1 5 6
Weekly flights 12 17 15
Flight time 3h 46m 3h 20m 3h 34m
Departure OTP 65% – –
San Francisco (SFO) to Chicago flights · San Jose (SJC) to Chicago flights · Santa Rosa (STS) to Chicago flights
Airports within 200 miles of OAK with service to Chicago Midway International Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
+2h
Chicago is 2 hours ahead of Oakland.
OAK: PDT · MDW: CDT

When it's 6:00 PM in Oakland, it's 8:00 PM in Chicago.
Distance & Flight Time
1,840 mi / 2,961 km
Nonstop flight time is approximately 3h 46m to 4h 5m.
Facts

OAK–MDW Quick Facts

Key statistics for the Oakland to Chicago route.
Route details
Distance1,840 mi / 2,961 km
Flight time3h 46m to 4h 5m
Time difference+2 hours
Airlines (nonstop)1
Weekly flights12 out / 13 return
1-stop connections98 hubs
Origin: OAK
Full nameSan Francisco Bay Oakland International Airport
IATA / ICAOOAK / KOAK
TimezoneAmerica/Los_Angeles
Passengers/yr10.6M
Elevation9 ft / 3 m
Destination: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
FAQ

Frequently Asked Questions

Common questions about OAK to MDW flights.
Nonstop flights from San Francisco Bay Oakland International Airport to Chicago Midway International Airport take approximately 3h 46m to 4h 5m. The route covers 1,840 miles.
1 airline operates nonstop service: Southwest Airlines.
There are approximately 12 nonstop flights per week from OAK to MDW. The return direction has about 13 weekly flights.
Yes, 1-stop connections are available through CMI, ENW, APC, NUQ, BJC, MRY, ASE, VNY, TRM, MKE, STS, BZN, TEX, APA, SAF, BOI, YIP, OMA, SCF, SBA, LUK, SJC, SNA, ICT, CLD, PSP, PGA, MSP, TUS, SDF, RNO, LCK, YVR, BKL, LNK, BNA, MEM, JAC, TYS, DWH, OKC, ADS, IAD, EUG, NEW, EGE, SJD, YYZ, GAI, BWI, CHS, MSY, BTV, AGS, TEB, ACY, DFW, MMU, ATL, BED, YOW, HPN, ISM, PHL, JAX, BDL, MCO, ISP, VRB, APF, YUL, BJX, BOS, OPF, PBI, FXE, BCT, FLL, MIA, STT, HOU, LGB, ABQ, ONT, PDX, PHX, LAX, LAS, DEN, SEA, GDL, SAN, DAL, AUS, SLC, BUR, HCR and CMA. These options provide additional schedule flexibility.
Chicago is 2 hours ahead of Oakland.
Yes, return flights from MDW to OAK are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include SFO, SJC and STS. See the Alternatives section for a full comparison.
Click the 'Search Flights' button to check availability and prices on Google Flights. You can also compare airlines and schedules on this page to find the best option.
See the On-Time Performance section for the latest delay data at both airports. This shows departure and arrival reliability to help you plan.
Route data is updated regularly from official airline schedules. On-time performance data comes from recent airport delay snapshots.

Flights from OAK to MDW

San Francisco Bay Oakland International Airport (OAK) and Chicago Midway International Airport (MDW) are connected by nonstop service from Southwest Airlines. With 12 weekly departures, this is a regularly served route.

OAK to MDW Flight Duration and Schedule

Nonstop flight time from OAK to MDW ranges from 3 hours 46 minutes to 4 hours 5 minutes. The route covers a distance of 1,840 miles (2,961 km). There are approximately 12 weekly flights outbound and 13 return, totaling 25 flights per week in both directions.

Connecting Options and Alternatives

98 one-stop connections are available, with the fastest taking approximately 5 hours via CMI. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include San Francisco (SFO), San Jose (SJC) and Santa Rosa (STS).