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

OAK Airport Page →
1,840 mi airlines charter/private 13/wk
On-time Some delays Frequent delays
Flight Schedule 9 flights Verified 2m ago
Also flown by charter / private operators.
Nonstop Charter / private 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop
✓
→
WN2211
WN Southwest
73H
5:05 AM
PDT T2
11:10 AM
CDT
4h 5m
81%
M T W T F S S
Prices
✓
→
WN2744
WN Southwest
738
5:10 AM
PDT T2
11:15 AM
CDT
4h 5m
81%
M T W T F S S
Prices
✓
→
WN2761
WN Southwest
73H
5:55 AM
PDT T2
12:00 PM
CDT
4h 5m
81%
M T W T F S S
Prices
✓
→
WN3059
WN Southwest
73H
11:55 PM
PDT T2
6:00 AM+1
CDT
4h 5m
81%
M T W T F S S
Prices
✓
←
WN3366
WN Southwest
738
10:10 AM
CDT
12:40 PM
PDT
4h 30m
44%
M T W T F S S
Prices
✓
←
WN2221
WN Southwest
7M8
1:20 PM
CDT
3:50 PM
PDT
4h 30m
44%
M T W T F S S
Prices
✓
←
WN1336
WN Southwest
7M8
4:30 PM
CDT
7:00 PM
PDT
4h 30m
44%
M T W T F S S
Prices
✓
←
WN2710
WN Southwest
B38M
9:00 PM
CDT
11:30 PM
PDT
4h 30m
44%
M T W T F S S
Prices
✓
←
WN4042
WN Southwest
7M8
9:55 PM
CDT
12:37 AM+1
PDT
4h 42m
44%
M T W T F S S
Prices

No flights match your filters.

No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.

✦ 1-Stop connections via 10 hubs
DEN Denver 5h 35m WN → WN Denver (DEN) to Chicago flights
LAS Las Vegas 5h 55m LXJWNXE → EJAGTWJTL Las Vegas (LAS) to Chicago flights
PHX Phoenix 6h WN → WN Phoenix (PHX) to Chicago flights
SLC Salt Lake City 6h 10m AFAMDL → WN Salt Lake City (SLC) to Chicago flights
BUR Burbank 6h 20m WNXE → EJAWN Burbank (BUR) to Chicago flights
SAN San Diego 6h 23m ASSISWN → WN San Diego (SAN) to Chicago flights
DAL Dallas 6h 25m DLXWN → JTLWN Dallas (DAL) to Chicago flights
LAX Los Angeles 6h 35m LXJPCJWN → WN Los Angeles (LAX) to Chicago flights
PDX Portland 6h 45m ASLXJWN → WN Portland (PDX) to Chicago flights
AUS Austin 6h 45m WN → EJALXJWN Austin (AUS) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Oakland to Chicago
2 carriers, 13 flights/week nonstop.
2 Airlines 1,840 mi 4h 5m nonstop +2h ahead

OAK–MDW is served by 2 airlines with nonstop service. Southwest Airlines leads the route. The flight covers 1,840 miles in approximately 4h 5m. Beyond nonstop, 1-stop connecting options are also available.

Also explore OAK Routes MDW Routes OAK Live Flights MDW Live Flights OAK Delays MDW Delays
All flights from Chicago (MDW) Chicago to Oakland flights
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 13 738, 73H 4h05 100% – –
SGX SGX 1 – – 100% – –
Aircraft on this route
738 Boeing 737-800 – WN
73H Boeing 737-800 (Winglets) – WN
Alliance coverage
Unaffiliated: SGX + WN (14 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
2
flights
Departure time distribution
12 AM6 AM12 PM6 PM12 AM
Morning departures
Afternoon/evening departures
4
Nonstop flights
13
Outbound / wk
14
Return / wk
Connections

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for OAK to MDW.
1-STOP
One-Stop Connections
24
Hubs
~5h
Fastest
~23h
Longest
DEN ~5h 35m MKE ~5h 42m LAS ~5h 55m PHX ~6h 0m SLC ~6h 10m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
960
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.
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
OAK → MDW
100%
Generally reliable. Most flights run on time.
Departing
100%
Arriving
80%
Return
MDW → OAK
100%
Generally reliable. Most flights run on time.
Departing
100%
Arriving
25%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. OAK delays → MDW delays →
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 2 8 7
Weekly flights 13 14 16
Flight time 4h 5m 3h 55m 3h 30m
Departure OTP 100% – –
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 4h 5m gate to gate.
Facts

OAK–MDW Quick Facts

Key statistics for the Oakland to Chicago route.
Route details
Distance1,840 mi / 2,961 km
Flight time4h 5m
Time difference+2 hours
Airlines (nonstop)2
Weekly flights13 out / 14 return
1-stop connectionsAvailable
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 about 4h 5m gate to gate. The route covers 1,840 miles.
2 airlines operate flights from OAK to MDW: Southwest Airlines, and others.
This route has daily service. Check the schedule above for departure days and times in each direction.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Denver, Harry Reid and Phoenix Sky Harbor.
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 13 weekly departures, this is a regularly served route.

OAK to MDW Flight Duration and Schedule

Nonstop flight time from OAK to MDW is about 4 hours 5 minutes gate to gate. The route covers a distance of 1,840 miles (2,961 km). There are approximately 13 weekly flights outbound and 14 return, totaling 27 flights per week in both directions.

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Denver, Harry Reid and Phoenix Sky Harbor. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include San Francisco (SFO), San Jose (SJC) and Santa Rosa (STS).