Connect in the morning. The same one-hour layover misses 8% of the time at 10 am and almost half the time at 8 pm.
Nonstops
Nonstop details →| United | SJC | ORD | 4h 24m | 92% | 1.7% | 293 | Flying now |
| Southwest | OAK | MDW | 4h 05m | 85% | 0.2% | 505 | Flying now |
| Southwest | SJC | MDW | 4h 05m | 85% | 0.2% | 519 | Flying now |
| United | SFO | ORD | 4h 26m | 78% | 0.9% | 3,830 | Flying now |
| Southwest | SFO | MDW | 4h 05m | 74% | 1.2% | 485 | Flying now |
| American | SFO | ORD | 4h 27m | 73% | 1.8% | 1,768 | Flying now |
| American | SJC | ORD | – | 100%few flights | 0.0% | 8 | Not flying now |
| Alaska | SFO | ORD | 4h 23m | 53%few flights | 5.3% | 19 | Not flying now |
Best connections, one ticket
Ranked by chance you reach Chicago on time. Total trip = scheduled departure to arrival, layover included (Chicago is 2 h ahead of San Francisco). Layovers up to 4 hours. Pick a connection for the details.
| UnitedDetails → | SFO 21:13 → TPA 05:38UA 649 | 2h 12m Tampa | TPA 07:50 → ORD 10:00 +1UA 2804 | 10h 47m | 99% | 96% |
| UnitedDetails → | SFO 23:59 → AUS 05:46UA 1807 | 2h 34m Austin | AUS 08:20 → ORD 11:17 +1UA 202 | 9h 18m | 100% | 94% |
| UnitedDetails → | SFO 23:59 → DFW 05:45UA 1722 | 4h 00m Dallas-Fort Worth | DFW 09:45 → ORD 12:26 +1UA 1114 | 10h 27m | 100% | 92% |
| UnitedDetails → | SFO 21:25 → BOS 06:21UA 796 | 1h 54m Boston | BOS 08:15 → ORD 10:12 +1UA 1834 | 10h 47m | 98% | 91% |
| UnitedDetails → | SFO 23:05 → IAD 07:30UA 1083 | 3h 01m Dulles | IAD 10:31 → ORD 11:53 +1UA 1252 | 10h 48m | 98% | 90% |
| DeltaDetails → | SFO 22:55 → DTW 06:30DL 335 | 3h 45m Detroit | DTW 10:15 → ORD 10:50 +1DL 3673 · flown by SkyWest | 9h 55m | 100% | 89% |
| AmericanDetails → | SFO 23:49 → CLT 08:05AA 1580 | 2h 56m Charlotte | CLT 11:01 → ORD 12:19 +1AA 2908 | 10h 30m | 100% | 89% |
| UnitedDetails → | SFO 16:47 → SAN 18:39UA 1561 | 3h 46m San Diego | SAN 22:25 → ORD 04:36 +1UA 1457 | 9h 49m | 99% | 88% |
| Tight connection: often missed | ||||||
| AmericanDetails → | SFO 13:39 → LAX 15:19AA 6188 · flown by SkyWest | 1h 06m Los Angeles | LAX 16:25 → ORD 23:00AA 2718 | 7h 21m | 50% | 31% |
| AmericanDetails → | SFO 11:24 → DFW 17:14AA 1849 | 1h 24m Dallas-Fort Worth | DFW 18:38 → ORD 21:22AA 1424 | 7h 58m | 69% | 26% |
| AmericanDetails → | SFO 11:24 → MIA 20:05AA 2565 | 49m Miami | MIA 20:54 → ORD 23:30AA 1881 | 10h 04m | 47% | 24% |
Same layover, different day-part
How often the first flight arrives too late to connect (45 min minimum), for one-ticket layovers of 45–80 minutes.
Delays build through the day, so an afternoon first leg eats the layover. A short connection is fine early in the morning and a gamble later on.
Mixing airlines
| American AA 1580 SFO 23:49 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details → |
3h 30m | 10h 46m | 100% | 96% |
| United UA 2117 SFO 21:17 → PIT American AA 4625 PIT 08:02 → ORD Connection details → |
2h 43m | 9h 43m | 100% | 94% |
| United UA 1939 SFO 21:23 → CMH Southwest WN 1197 CMH 09:00 → MDW Connection details → |
3h 45m | 9h 47m | 100% | 93% |
Rank all connections, any airlines →
Regional partners count as the airline that sells them: SkyWest flying Delta Connection is one Delta ticket.
About this data: US DOT on-time records, Aug 2025 – Jul 2026, all US airlines; regional flights count under the airline that sells them. Schedules (which flights and connections exist, and their times) are as of Jun 6 – Jul 31, 2026; seasonal flights outside that window aren’t ranked. Rebuilt monthly. JSON