San Francisco Bay Area to Chicago (MDW) flight deals
Compare San Francisco Bay Area to Chicago (MDW) flights across upcoming months. See dated fares below, or choose your own dates and travelers.
Fare examples by month
Round-trip totals · Economy · USD. Choose a month to see the dates.
| Month | Travelers / trip length | Axel Member | Airline fare |
|---|---|---|---|
| October 2026 | 1 adult · 7 days | $231–$485 | $258–$539 |
| November 2026 | 1 adult · 3–7 days | $253–$596 | $284–$667 |
| December 2026 | 1 adult · 7 days | $390–$674 | $437–$753 |
| January 2027 | 1 adult · 7 days | $301 | $337 |
| March 2027 | 1 adult · 7–14 days | $312 | $351 |
| April 2027 | 1 adult · 7–14 days | $328 | $365 |
| May 2027 | 1 adult · 7 days | $328 | $365 |
Fares observed September 22 – 24, 2026. USD for the travelers shown. Search a trip for current prices. For starting totals, choose a return flight to confirm the final price.
October 2026
1 adult · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| SFO | Oct 6–13, 2026 · 7 days | Nonstop / Nonstop · 4h 10m / 4h 45m | $400 · Save $48 | $448 | Check Axel prices |
| SJC | Oct 6–13, 2026 · 7 days | Nonstop / 1 stop · 4h 0m / 6h 55m | $429 · Save $53 | $482 | Check Axel prices |
| SJC | Oct 6–13, 2026 · 7 days | Nonstop / Nonstop · 4h 0m / 4h 35m | $466 · Save $54 | $520 | Check Axel prices |
| OAK | Oct 6–13, 2026 · 7 days | Nonstop / 1 stop · 4h 0m / 6h 20m | $398 · Save $47 | $445 | Check Axel prices |
| OAK | Oct 6–13, 2026 · 7 days | Nonstop / Nonstop · 4h 0m / 4h 40m | $485 · Save $54 | $539 | Check Axel prices |
| SFO | Oct 20–27, 2026 · 7 days | 1 stop / 1 stop · 12h 36m / 10h 17m | $231 · Save $27 | $258 | Check Axel prices |
| SJC | Oct 20–27, 2026 · 7 days | Nonstop / Nonstop · 4h 0m / 4h 35m | $301 · Save $36 | $337 | Check Axel prices |
| OAK | Oct 20–27, 2026 · 7 days | Nonstop / Nonstop · 4h 0m / 4h 45m | $301 · Save $36 | $337 | Check Axel prices |
November 2026
1 adult · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| SJC | Nov 2–5, 2026 · 3 days | Nonstop / Nonstop · 4h 0m / 4h 40m | $301 · Save $36 | $337 | Check Axel prices |
| SFO | Nov 2–5, 2026 · 3 days | 1 stop / 1 stop · 9h 30m / 12h 9m | $260 · Save $30 | $290 | Check Axel prices |
| OAK | Nov 6–13, 2026 · 7 days | Nonstop / Nonstop · 4h 5m / 4h 45m | $327 · Save $36 | $363 | Check Axel prices |
| SJC | Nov 6–13, 2026 · 7 days | Nonstop / Nonstop · 4h 0m / 4h 40m | $367 · Save $42 | $409 | Check Axel prices |
| SFO | Nov 6–13, 2026 · 7 days | 1 stop / 1 stop · 9h 33m / 12h 9m | $253 · Save $31 | $284 | Check Axel prices |
| OAK | Nov 20–27, 2026 · 7 days | 1 stop / 2 stops · 6h 10m / 8h 50m | $381 · Save $47 | $428 | Check Axel prices |
| OAK | Nov 20–27, 2026 · 7 days | 1 stop / Nonstop · 6h 10m / 4h 40m | $596 · Save $71 | $667 | Check Axel prices |
December 2026
1 adult · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| OAK | Dec 6–13, 2026 · 7 days | Nonstop / Nonstop · 4h 0m / 4h 40m | $390 · Save $47 | $437 | Check Axel prices |
| SJC | Dec 6–13, 2026 · 7 days | Nonstop / Nonstop · 4h 0m / 4h 40m | $409 · Save $48 | $457 | Check Axel prices |
| OAK | Dec 20–27, 2026 · 7 days | Nonstop / Nonstop · 4h 5m / 4h 50m | $576 · Save $71 | $647 | Check Axel prices |
| SFO | Dec 20–27, 2026 · 7 days | 1 stop / 1 stop · 9h 2m / 7h 36m | $634 · Save $74 | $708 | Check Axel prices |
| SJC | Dec 20–27, 2026 · 7 days | Nonstop / 1 stop · 4h 0m / 11h 10m | $566 · Save $67 | $633 | Check Axel prices |
| SJC | Dec 20–27, 2026 · 7 days | Nonstop / Nonstop · 4h 0m / 4h 40m | $674 · Save $79 | $753 | Check Axel prices |
1 adult · Economy · Round-trip starting totals
| From | Travel dates | Outbound flight | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| SFO | Dec 6–13, 2026 · 7 days | 1 stop · 14h 14m | From $351 · Save $43 | From $394 | Check Axel prices |
| SFO | Dec 6–13, 2026 · 7 days | Nonstop · 4h 5m | From $390 · Save $47 | From $437 | Check Axel prices |
January 2027
1 adult · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| SFO | Jan 6–13, 2027 · 7 days | Nonstop / Nonstop · 4h 0m / 4h 40m | $301 · Save $36 | $337 | Check Axel prices |
| SFO | Jan 20–27, 2027 · 7 days | Nonstop / Nonstop · 4h 0m / 4h 40m | $301 · Save $36 | $337 | Check Axel prices |
March 2027
Round-trip totals in USD for 1 adult · Economy.
| From | Destination | Trip dates | Days | Axel Member | Airline fare | Stops | Search |
|---|---|---|---|---|---|---|---|
| OAK | Chicago (MDW) | Mar 2–9, 2027 | 7 | $312 · Save $39 | $351 | Nonstop | Check Axel prices |
| OAK | Chicago (MDW) | Mar 2–16, 2027 | 14 | $312 · Save $39 | $351 | Nonstop | Check Axel prices |
April 2027
Round-trip totals in USD for 1 adult · Economy.
| From | Destination | Trip dates | Days | Axel Member | Airline fare | Stops | Search |
|---|---|---|---|---|---|---|---|
| OAK | Chicago (MDW) | Apr 6–13, 2027 | 7 | $328 · Save $37 | $365 | Nonstop | Check Axel prices |
| OAK | Chicago (MDW) | Apr 6–20, 2027 | 14 | $328 · Save $37 | $365 | Nonstop | Check Axel prices |
May 2027
Round-trip totals in USD for 1 adult · Economy · 7 days.
| From | Destination | Trip dates | Axel Member | Airline fare | Stops | Search |
|---|---|---|---|---|---|---|
| OAK | Chicago (MDW) | May 4–11, 2027 | $328 · Save $37 | $365 | Nonstop | Check Axel prices |
Non-members can also book and save on airline fares. Live search shows prices with and without Membership. Optional Membership: $15 for the first month, then $10/month. Cancel anytime.
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