Cheap flights Chicago (MDW) to San Francisco Bay Area (SFO)
Chicago to San Francisco Bay Area is a 2189-mile trip. We compared 6 nearby airports on both ends, pricing the flight plus the drive, parking, and rideshare that flight search engines leave out.
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Search MDW → SFONearest vs. cheapest door-to-door
| Choice | Airports | Est. flight | Est. ground | Est. total |
|---|---|---|---|---|
| Nearest airports | MDW → SFO | $465 | $104 | $570 |
| Cheapest combo | MDW → SFO | $465 | $104 | $570 |
Departure airports near Chicago
| Airport | Drive | Parking/day | Est. flight to SFO | Est. total (4-night trip) |
|---|---|---|---|---|
| MDW — Chicago | 10.2 mi / 15m | $68 | $465 | $533 |
| ORD — Chicago | 18.4 mi / 24m | $86 | $459 | $546 |
| SBN — South Bend | 80.8 mi / 1h 17m | $92 | $529 | $622 |
Arrival airports near San Francisco Bay Area
| Airport | From downtown | Est. rideshare | Est. flight from MDW | Est. total (4-night trip) |
|---|---|---|---|---|
| SFO — San Francisco | 12.9 mi / 18m | $37 | $465 | $502 |
| OAK — Oakland | 13.6 mi / 19m | $38 | $501 | $539 |
| SJC — San Jose | 46.3 mi / 48m | $109 | $480 | $589 |
The drive itself
Driving direct is about 2189 miles, 1d 12h, and an estimated $384 in gas and wear, one-way. All fares and ground costs on this page are modeled estimates from route economics and drive-time math, not live quotes — run the search above for current pricing.
Nearby airport guides
Related routes
White Plains → Oakland (HPN→OAK)Newark → San Francisco (EWR→SFO)New York LaGuardia → Chicago (LGA→ORD)Boston → San Francisco (BOS→SFO)New York JFK → San Francisco (JFK→SFO)Los Angeles → Chicago (LAX→ORD)
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