Your next trip, last seen at €76
Lowest observedWhen to fly
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The lowest fare we observed for each month. Open a month to see its days, then pick your outbound and return. A day with no price is one we will search for you.
One-way fare
- Lowest observed
- €76, departing 2 Dec 2026 (Last checked: 24 Oct 2026)One-way fare · Priced departure days checked in the last 14 days: 186Check live prices for this route
- Airlines seen
- Southwest Airlines, Alaska Airlines, Delta Air Lines, Frontier Airlines
- Reported fastest flight
- 5h 09m
- Non-stop
- Yes
About this route
Explore the fares we observed from Oakland to Chicago. Prices move often, so pick your dates to see the latest options.
- Route distance
- 2,972 km
- Reported fastest flight
- 5h 09m
- Alternative airports
- CGX, DPA, MDW, PWK, RFD
Route-level information; individual journeys vary.
Published schedules report non-stop service with Southwest Airlines. Check current timetables.
A clearer picture of your fare
Airport to city: straight-line distance
- Oakland San Francisco Bay Airport (OAK) → Oakland, city gazetteer reference point (37.8044, -122.2711): ≈ 10 km.
- Chicago Midway International Airport (MDW) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 14 km.
- Chicago O'Hare International Airport (ORD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 25 km.
- Chicago Rockford International Airport (RFD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 126 km.
Approximate distances calculated from coordinates, not road distances or travel times. These airports serve the city; they are not confirmed endpoints of an offer.
Lowest fare by departure month
Cheapest month from Oakland to Chicago: December 2026, from €76 (checked 24 Oct 2026).
| Month | Lowest fare | Priced days |
|---|---|---|
| November 2026 | €97 | 17 |
| December 2026 | €76 | 31 |
| January 2027 | €77 | 31 |
| February 2027 | €97 | 28 |
| March 2027 | €108 | 31 |
| April 2027 | €172 | 30 |
| May 2027 | €172 | 18 |
Lowest fare by day of the week
Cheapest day of the week from Oakland to Chicago: Tuesday, from €76 (checked 24 Oct 2026).
| Day | Lowest fare | Priced days |
|---|---|---|
| Monday | €85 | 27 |
| Tuesday | €76 | 27 |
| Wednesday | €76 | 26 |
| Thursday | €86 | 26 |
| Friday | €80 | 26 |
| Saturday | €76 | 27 |
| Sunday | €105 | 27 |
One-way fares checked in the last 14 days. Each figure is the lowest priced departure day we saw, not a guaranteed fare.
Lowest fare by days before departure
Lowest fare from Oakland to Chicago by days until departure (31 to 60 days): €76 (checked 24 Oct 2026).
| Days before departure | Lowest fare | Priced days |
|---|---|---|
| 8 to 30 days | €97 | 15 |
| 31 to 60 days | €76 | 30 |
| 61 days or more | €77 | 141 |
One-way fares checked in the last 14 days. Each figure is the lowest stored fare for that distance to departure, not a price forecast.
Fares for different departure dates, checked now; not a guide to when to book.
Lowest one-way fare we saw per airline
Cheapest airline from Oakland to Chicago: Frontier Airlines, from €76 (checked 24 Oct 2026).
| Airline | Lowest fare | Priced days |
|---|---|---|
| Frontier Airlines | €76Dec 2, 2026 | 6 |
| Alaska Airlines | €118Dec 2, 2026 | 6 |
| Delta Air Lines | €118Dec 2, 2026 | 6 |
One-way fares checked in the last 14 days. An airline listed here had a fare on at least 3 departure days. Each figure is the lowest we saw, not a guaranteed fare. Connecting itineraries are included; the date is the departure day of that fare.
Frequently asked
How much is a flight from Oakland to Chicago?
The lowest fare Routavio has observed is €76, found on 24 Oct 2026. Prices move, so read it as a floor rather than a quote.
When is the cheapest month to fly from Oakland to Chicago?
Cheapest month from Oakland to Chicago: December 2026, from €76 (checked 24 Oct 2026).
Are there direct flights from Oakland to Chicago?
Yes. Published schedules report non-stop flights on this route with Southwest Airlines.
Which airlines fly from Oakland to Chicago?
Routavio has seen these carriers on the route: Southwest Airlines, Alaska Airlines, Delta Air Lines, Frontier Airlines.
How many of the observed Oakland to Chicago fares were non-stop?
1 of the 4 fares we observed were non-stop; the rest included at least one stop. That describes our observations, not every flight that operates.
Which day of the week is cheapest from Oakland to Chicago?
Cheapest day of the week from Oakland to Chicago: Tuesday, from €76 (checked 24 Oct 2026).
Which airline has the lowest fare from Oakland to Chicago?
Cheapest airline from Oakland to Chicago: Frontier Airlines, from €76 (checked 24 Oct 2026).
How observed prices work, what "No data" means and what a fare includes: Read the flight price guide
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Recently observed fares. Prices may change.
Last checked: 24 Oct 2026