San Francisco Bay Area to Chicago (O’Hare or Midway) flight deals
Compare San Francisco Bay Area to Chicago (O’Hare or Midway) 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 | 2 adults · 3 days | $743–$1,048 | $830–$1,170 |
| October 2026 | 1 adult · 7 days | $211 | $236 |
| November 2026 | 1 adult · 3–14 days | $231–$301 | $258–$337 |
| November 2026 | 2 adults · 4 days | $516 | $576 |
| December 2026 | 2 adults · 7 days | $733–$1,353 | $816–$1,512 |
| December 2026 | 1 adult · 7–14 days | $234–$238 | $263–$264 |
| January 2027 | 2 adults · 3 days | $515–$625 | $574–$700 |
| January 2027 | 1 adult · 7–14 days | $185–$278 | $208–$309 |
| February 2027 | 2 adults · 3 days | $487 | $544 |
| February 2027 | 1 adult · 7–14 days | $163–$288 | $182–$320 |
| March 2027 | 1 adult · 7–14 days | $241–$312 | $270–$351 |
| April 2027 | 2 adults · 7 days | $634–$645 | $707–$725 |
| April 2027 | 1 adult · 7–14 days | $309–$328 | $345–$365 |
| May 2027 | 2 adults · 3 days | $654 | $728 |
| May 2027 | 1 adult · 7–14 days | $320–$328 | $357–$365 |
| June 2027 | 2 adults · 2 days | $733 | $820 |
| June 2027 | 1 adult · 7–14 days | $320–$347 | $357–$385 |
| July 2027 | 2 adults · 3 days | $645 | $725 |
| July 2027 | 1 adult · 7–14 days | $309–$351 | $345–$394 |
Fares observed September 22, 2026. USD for the travelers shown. Search a trip for current prices.
October 2026
2 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| SFO | Oct 9–12, 2026 · 3 days | 1 stop / 1 stop · 9h 9m / 18h 43m | $743 · Save $87 | $830 | Check Axel prices |
| SFO | Oct 9–12, 2026 · 3 days | 1 stop / 1 stop · 9h 9m / 6h 35m | $1,048 · Save $122 | $1,170 | Check Axel prices |
Round-trip totals in USD for 1 adult · Economy · 7 days.
| From | Destination | Trip dates | Axel Member | Airline fare | Stops | Search |
|---|---|---|---|---|---|---|
| SJC | Chicago (ORD) | Oct 22–29, 2026 | $211 · Save $25 | $236 | 1 stop | Check Axel prices |
November 2026
1 adult · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| SFO | Nov 2–5, 2026 · 3 days | 1 stop / 1 stop · 9h 30m / 12h 9m | $260 · Save $30 | $290 | Check Axel prices |
| SJC | Nov 2–5, 2026 · 3 days | Nonstop / Nonstop · 4h 0m / 4h 40m | $301 · Save $36 | $337 | Check Axel prices |
| SJC | Nov 2–5, 2026 · 3 days | 1 stop / 1 stop · 12h 32m / 22h 31m | $269 · Save $31 | $300 | Check Axel prices |
| SFO | Nov 2–5, 2026 · 3 days | 1 stop / 1 stop · 12h 34m / 6h 47m | $231 · Save $27 | $258 | Check Axel prices |
2 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| SFO | Nov 11–15, 2026 · 4 days | 1 stop / 1 stop · 7h 43m / 6h 47m | $516 · Save $60 | $576 | Check Axel prices |
Round-trip totals in USD for 1 adult · Economy · 14 days.
| From | Destination | Trip dates | Axel Member | Airline fare | Stops | Search |
|---|---|---|---|---|---|---|
| SJC | Chicago (ORD) | Nov 12–26, 2026 | $238 · Save $26 | $264 | 1 stop | Check Axel prices |
December 2026
2 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| SFO | Dec 19–26, 2026 · 7 days | Nonstop / 1 stop · 4h 23m / 11h 44m | $950 · Save $110 | $1,060 | Check Axel prices |
| SFO | Dec 19–26, 2026 · 7 days | Nonstop / Nonstop · 4h 23m / 4h 54m | $1,353 · Save $159 | $1,512 | Check Axel prices |
| SFO | Dec 26, 2026–Jan 2, 2027 · 7 days | 1 stop / 1 stop · 12h 17m / 26h 16m | $733 · Save $83 | $816 | Check Axel prices |
| SFO | Dec 26, 2026–Jan 2, 2027 · 7 days | 1 stop / 1 stop · 12h 17m / 10h 52m | $1,282 · Save $157 | $1,439 | Check Axel prices |
Round-trip totals in USD for 1 adult · Economy.
| From | Destination | Trip dates | Days | Axel Member | Airline fare | Stops | Search |
|---|---|---|---|---|---|---|---|
| OAK | Chicago (ORD) | Dec 1–15, 2026 | 14 | $234 · Save $29 | $263 | 1 stop | Check Axel prices |
| SJC | Chicago (ORD) | Dec 3–10, 2026 | 7 | $238 · Save $26 | $264 | 1 stop | Check Axel prices |
January 2027
2 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| SFO | Jan 15–18, 2027 · 3 days | 1 stop / 1 stop · 25h 11m / 20h 14m | $515 · Save $59 | $574 | Check Axel prices |
| SFO | Jan 15–18, 2027 · 3 days | 1 stop / 1 stop · 25h 11m / 12h 4m | $625 · Save $75 | $700 | Check Axel prices |
Round-trip totals in USD for 1 adult · Economy.
| From | Destination | Trip dates | Days | Axel Member | Airline fare | Stops | Search |
|---|---|---|---|---|---|---|---|
| OAK | Chicago (ORD) | Jan 7–21, 2027 | 14 | $278 · Save $31 | $309 | 1 stop | Check Axel prices |
| SJC | Chicago (ORD) | Jan 14–21, 2027 | 7 | $260 · Save $30 | $290 | 1 stop | Check Axel prices |
| SFO | Chicago (ORD) | Jan 25–Feb 1, 2027 | 7 | $185 · Save $23 | $208 | 1 stop | Check Axel prices |
February 2027
2 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| SFO | Feb 12–15, 2027 · 3 days | 1 stop / 1 stop · 16h 11m / 10h 57m | $487 · Save $57 | $544 | Check Axel prices |
Round-trip totals in USD for 1 adult · Economy.
| From | Destination | Trip dates | Days | Axel Member | Airline fare | Stops | Search |
|---|---|---|---|---|---|---|---|
| OAK | Chicago (ORD) | Feb 3–10, 2027 | 7 | $288 · Save $32 | $320 | 1 stop | Check Axel prices |
| OAK | Chicago (ORD) | Feb 3–17, 2027 | 14 | $288 · Save $32 | $320 | 1 stop | Check Axel prices |
| SFO | Chicago (ORD) | Feb 10–24, 2027 | 14 | $163 · Save $19 | $182 | 1 stop | Check Axel prices |
| SJC | Chicago (ORD) | Feb 11–25, 2027 | 14 | $229 · Save $26 | $255 | 1 stop | 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 |
| SFO | Chicago (ORD) | Mar 1–8, 2027 | 7 | $241 · Save $29 | $270 | 1 stop | Check Axel prices |
| SFO | Chicago (ORD) | Mar 1–15, 2027 | 14 | $241 · Save $29 | $270 | 1 stop | Check Axel prices |
| SJC | Chicago (ORD) | Mar 1–15, 2027 | 14 | $260 · Save $31 | $291 | 1 stop | Check Axel prices |
| SJC | Chicago (ORD) | Mar 2–9, 2027 | 7 | $292 · Save $35 | $327 | 1 stop | Check Axel prices |
April 2027
2 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| SFO | Apr 10–17, 2027 · 7 days | 1 stop / 1 stop · 8h 55m / 7h 46m | $634 · Save $73 | $707 | Check Axel prices |
| SFO | Apr 10–17, 2027 · 7 days | 1 stop / 1 stop · 8h 55m / 6h 43m | $645 · Save $80 | $725 | Check Axel prices |
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 |
| SJC | Chicago (ORD) | Apr 6–13, 2027 | 7 | $320 · Save $37 | $357 | 1 stop | Check Axel prices |
| SJC | Chicago (ORD) | Apr 6–20, 2027 | 14 | $320 · Save $37 | $357 | 1 stop | Check Axel prices |
| SFO | Chicago (ORD) | Apr 13–27, 2027 | 14 | $309 · Save $36 | $345 | 1 stop | Check Axel prices |
May 2027
2 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| SFO | May 28–31, 2027 · 3 days | 1 stop / Nonstop · 8h 55m / 4h 58m | $654 · Save $74 | $728 | Check Axel prices |
Round-trip totals in USD for 1 adult · Economy.
| From | Destination | Trip dates | Days | Axel Member | Airline fare | Stops | Search |
|---|---|---|---|---|---|---|---|
| OAK | Chicago (MDW) | May 4–11, 2027 | 7 | $328 · Save $37 | $365 | Nonstop | Check Axel prices |
| SJC | Chicago (ORD) | May 1–8, 2027 | 7 | $320 · Save $37 | $357 | 1 stop | Check Axel prices |
| SJC | Chicago (ORD) | May 1–15, 2027 | 14 | $320 · Save $37 | $357 | 1 stop | Check Axel prices |
June 2027
2 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| SFO | Jun 18–20, 2027 · 2 days | Nonstop / Nonstop · 4h 29m / 4h 50m | $733 · Save $87 | $820 | Check Axel prices |
Round-trip totals in USD for 1 adult · Economy.
| From | Destination | Trip dates | Days | Axel Member | Airline fare | Stops | Search |
|---|---|---|---|---|---|---|---|
| SJC | Chicago (ORD) | Jun 1–8, 2027 | 7 | $320 · Save $37 | $357 | 1 stop | Check Axel prices |
| SJC | Chicago (ORD) | Jun 1–15, 2027 | 14 | $320 · Save $37 | $357 | 1 stop | Check Axel prices |
| OAK | Chicago (ORD) | Jun 17–Jul 1, 2027 | 14 | $347 · Save $39 | $385 | 1 stop | Check Axel prices |
July 2027
2 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| SFO | Jul 2–5, 2027 · 3 days | 1 stop / 1 stop · 10h 15m / 6h 43m | $645 · Save $80 | $725 | Check Axel prices |
Round-trip totals in USD for 1 adult · Economy.
| From | Destination | Trip dates | Days | Axel Member | Airline fare | Stops | Search |
|---|---|---|---|---|---|---|---|
| SJC | Chicago (ORD) | Jul 2–9, 2027 | 7 | $320 · Save $37 | $357 | 1 stop | Check Axel prices |
| SJC | Chicago (ORD) | Jul 2–16, 2027 | 14 | $320 · Save $37 | $357 | 1 stop | Check Axel prices |
| OAK | Chicago (ORD) | Jul 6–20, 2027 | 14 | $351 · Save $43 | $394 | 1 stop | Check Axel prices |
| SFO | Chicago (ORD) | Jul 6–20, 2027 | 14 | $309 · Save $36 | $345 | 1 stop | 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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