Oakland to Chicago/Prospect Heights/Wheeling (OAK–PWK) — Airlines, Schedules & Connections

OAK Airport Page →
1,831 mi airlines 1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 43 1-stop flights Verified 4d ago
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  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

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/Prospect Heights/Wheeling
Connecting service available through multiple hubs.
1 Flights/wk 1,831 mi 3h 29m nonstop +2h ahead 43 1-stop hubs

While no nonstop service exists between OAK and PWK, connecting options are available through 43 hubs.

Also explore OAK Routes PWK Routes OAK Live Flights PWK Live Flights OAK Delays
Connections

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for OAK to PWK.
1-STOP
One-Stop Connections
43
Hubs
~5h
Fastest
~29h
Longest
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
47
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/Prospect Heights/Wheeling from Oakland

Nearby airports with service to Chicago Executive Airport.
Metric OAK→PWK SFO→PWK SJC→PWK
Distance from OAK – 11 mi 29 mi
Nonstop airlines 0 3 1
Weekly flights 1 1 1
Flight time 3h 29m 4h 29m 3h 42m
Departure OTP 100% – –
San Francisco (SFO) to Chicago/Prospect Heights/Wheeling flights · San Jose (SJC) to Chicago/Prospect Heights/Wheeling flights
Airports within 200 miles of OAK with service to Chicago Executive Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
+2h
Chicago/Prospect Heights/Wheeling is 2 hours ahead of Oakland.
OAK: PDT · PWK: CDT

When it's 6:00 PM in Oakland, it's 8:00 PM in Chicago/Prospect Heights/Wheeling.
Distance & Flight Time
1,831 mi / 2,947 km
Nonstop flight time is approximately 3h 29m.
Facts

OAK–PWK Quick Facts

Key statistics for the Oakland to Chicago/Prospect Heights/Wheeling route.
Route details
Distance1,831 mi / 2,947 km
Flight time3h 29m
Time difference+2 hours
Airlines (nonstop)0
Weekly flights1 out
1-stop connections43 hubs
Origin: OAK
Full nameSan Francisco Bay Oakland International Airport
IATA / ICAOOAK / KOAK
TimezoneAmerica/Los_Angeles
Passengers/yr10.6M
Elevation9 ft / 3 m
Destination: PWK
Full nameChicago Executive Airport
IATA / ICAOPWK / KPWK
TimezoneAmerica/Chicago
Elevation647 ft / 197 m
FAQ

Frequently Asked Questions

Common questions about OAK to PWK flights.
Nonstop flights from San Francisco Bay Oakland International Airport to Chicago Executive Airport take approximately 3h 29m. The route covers 1,831 miles.
There are approximately 1 nonstop flights per week from OAK to PWK.
Yes, 1-stop connections are available through MKE, ENW, OMA, VNY, SJC, MSP, OKC, LAS, TUS, SLC, PSP, PHX, BNA, MDW, LGB, YYZ, SAN, DEN, DAL, TYS, LAX, SNA, BZN, AUS, DFW, ADS, HOU, SJD, IAD, CHS, MSY, BFI, BDL, PHL, ATL, MCO, BOS, HYA, PBI, FLL, MIA, ANC and HND. These options provide additional schedule flexibility.
Chicago/Prospect Heights/Wheeling is 2 hours ahead of Oakland.
Nearby alternatives include SFO and SJC. 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 PWK

San Francisco Bay Oakland International Airport (OAK) and Chicago Executive Airport (PWK) are connected through multiple connecting hub airports.

OAK to PWK Flight Duration and Schedule

Nonstop flight time from OAK to PWK ranges from 3 hours 29 minutes. The route covers a distance of 1,831 miles (2,947 km).

Connecting Options and Alternatives

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