Connect in the morning. The same one-hour layover misses 1 time in 10 at 11 am and barely half the time at 10 pm.
Nonstops
Nonstop details →| Southwest | MDW | BWI | 1h 50m | 80% | 2.7% | 1,786 | Flying now |
| United | ORD | IAD | 2h 01m | 77% | 0.8% | 2,082 | Flying now |
| American | ORD | BWI | 2h 03m | 76% | 3.9% | 1,199 | Flying now |
| United | ORD | DCA | 2h 03m | 71% | 2.6% | 4,083 | Flying now |
| United | ORD | BWI | 2h 04m | 71% | 1.4% | 1,241 | Flying now |
| Southwest | MDW | DCA | 1h 50m | 71% | 1.9% | 2,100 | Flying now |
| American | ORD | DCA | 2h 00m | 69% | 3.6% | 2,959 | Flying now |
| Frontier | MDW | BWI | 1h 56m | 83% | 1.4% | 71 | Not flying now |
| Southwest | ORD | BWI | 2h 05m | 73% | 0.0% | 93 | Not flying now |
| Frontier | ORD | BWI | 2h 05m | 67% | 4.3% | 140 | Not flying now |
| Spirit | ORD | BWI | – | 89%few flights | 0.0% | 18 | Not flying now |
Best connections, one ticket
Ranked by chance you reach Washington on time. Total trip = scheduled departure to arrival, layover included (Washington is 1 h ahead of Chicago). Layovers up to 4 hours. Pick a connection for the details.
| SouthwestDetails → | MDW 07:40 → PVD 10:55WN 784 | 2h 07m Providence | PVD 13:02 → BWI 14:28WN 1094 | 5h 47m | 100% | 94% |
| UnitedDetails → | ORD 05:00 → DEN 06:42UA 2666 | 1h 18m Denver | DEN 08:00 → IAD 13:26UA 1101 | 7h 26m | 99% | 92% |
| SouthwestDetails → | MDW 07:40 → BOS 10:55WN 4611 | 2h 25m Boston | BOS 13:20 → BWI 15:00WN 733 | 6h 20m | 100% | 91% |
| SouthwestDetails → | MDW 07:40 → RDU 10:35WN 852 | 2h 45m Raleigh/Durham | RDU 13:20 → BWI 14:35WN 297 | 5h 55m | 100% | 88% |
| UnitedDetails → | ORD 07:43 → SYR 10:48UA 4541 · flown by GoJet | 3h 52m Syracuse | SYR 14:40 → IAD 16:06UA 4505 · flown by GoJet | 7h 23m | 100% | 88% |
| SouthwestDetails → | MDW 05:00 → TPA 08:25WN 2906 | 2h 15m Tampa | TPA 10:40 → BWI 13:00WN 1016 | 7h 00m | 100% | 88% |
| UnitedDetails → | ORD 07:00 → SAV 10:23UA 2622 | 1h 42m Savannah | SAV 12:05 → IAD 13:45UA 2057 | 5h 45m | 96% | 88% |
| UnitedDetails → | ORD 05:30 → IAH 08:18UA 2310 | 1h 29m Houston | IAH 09:47 → DCA 13:57UA 2670 | 7h 27m | 99% | 86% |
| Tight connection: often missed | ||||||
| UnitedDetails → | ORD 10:51 → EWR 14:17UA 1856 | 51m Newark | EWR 15:08 → IAD 16:32UA 1992 | 4h 41m | 72% | 46% |
| AmericanDetails → | ORD 14:59 → DFW 17:36AA 2257 | 1h 08m Dallas-Fort Worth | DFW 18:44 → IAD 22:46AA 1132 | 6h 53m | 68% | 30% |
| AmericanDetails → | ORD 16:05 → MIA 20:26AA 2910 | 51m Miami | MIA 21:17 → BWI 23:54AA 3216 | 6h 49m | 27% | 15% |
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 4500 ORD 08:10 → RIC United UA 4549 RIC 15:00 → IAD Connection details → |
3h 30m | 6h 55m | 100% | 91% |
| United UA 1076 ORD 07:33 → BOS Southwest WN 733 BOS 13:20 → BWI Connection details → |
2h 15m | 6h 27m | 99% | 90% |
| Southwest WN 2815 MDW 05:10 → MCO American AA 2088 MCO 10:40 → DCA Connection details → |
2h 00m | 6h 49m | 95% | 87% |
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