Connect in the morning. The same one-hour layover misses 1 time in 10 at 12 pm and almost half the time at 7 pm.
Nonstops
Nonstop details →| American | BWI | ORD | 2h 28m | 78% | 3.7% | 1,199 | Flying now |
| Southwest | DCA | MDW | 2h 05m | 78% | 2.7% | 2,099 | Flying now |
| Southwest | BWI | MDW | 2h 05m | 77% | 2.2% | 1,767 | Flying now |
| United | IAD | ORD | 2h 14m | 76% | 1.0% | 2,085 | Flying now |
| United | DCA | ORD | 2h 20m | 76% | 3.1% | 4,083 | Flying now |
| United | BWI | ORD | 2h 18m | 75% | 1.2% | 1,239 | Flying now |
| American | DCA | ORD | 2h 26m | 75% | 3.9% | 2,965 | Flying now |
| Southwest | BWI | ORD | 2h 15m | 90% | 0.0% | 93 | Not flying now |
| Frontier | BWI | MDW | 2h 04m | 77% | 1.4% | 71 | Not flying now |
| Frontier | BWI | ORD | 2h 24m | 68% | 4.3% | 140 | Not flying now |
| Spirit | BWI | ORD | – | 89%few flights | 0.0% | 18 | 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 1 h behind Washington). Layovers up to 4 hours. Pick a connection for the details.
| AmericanDetails → | DCA 07:29 → DAY 09:04AA 5159 · flown by PSA | 3h 25m Dayton | DAY 12:29 → ORD 12:54AA 3786 · flown by Envoy | 6h 25m | 100% | 96% |
| SouthwestDetails → | BWI 08:15 → CLT 09:55WN 148 | 1h 40m Charlotte | CLT 11:35 → MDW 12:35WN 4529 | 5h 20m | 96% | 92% |
| SouthwestDetails → | BWI 10:55 → ALB 12:15WN 155 | 3h 05m Albany | ALB 15:20 → MDW 16:35WN 164 | 6h 40m | 100% | 89% |
| SouthwestDetails → | BWI 06:20 → ATL 08:15WN 4689 | 1h 45m Atlanta | ATL 10:00 → MDW 11:00WN 224 | 5h 40m | 100% | 89% |
| AmericanDetails → | DCA 07:45 → MCO 10:14AA 3273 | 1h 24m Orlando | MCO 11:38 → ORD 13:45AA 2067 | 7h 00m | 97% | 89% |
| AmericanDetails → | DCA 06:55 → BOS 08:34AA 1605 | 1h 55m Boston | BOS 10:29 → ORD 12:30AA 3022 | 6h 34m | 100% | 88% |
| UnitedDetails → | IAD 08:25 → CHS 10:11UA 1108 | 1h 20m Charleston | CHS 11:31 → ORD 13:09UA 592 | 5h 44m | 99% | 87% |
| AmericanDetails → | BWI 06:15 → CLT 07:53AA 2670 | 3h 08m Charlotte | CLT 11:01 → ORD 12:19AA 2908 | 7h 04m | 98% | 87% |
| Tight connection: often missed | ||||||
| DeltaDetails → | BWI 17:32 → DTW 19:14DL 2480 | 46m Detroit | DTW 20:00 → ORD 20:31DL 1665 | 3h 59m | 71% | 44% |
| AmericanDetails → | DCA 15:18 → DFW 17:49AA 1624 | 49m Dallas-Fort Worth | DFW 18:38 → ORD 21:22AA 1424 | 7h 04m | 74% | 27% |
| DeltaDetails → | IAD 12:29 → JFK 13:58DL 5835 · flown by Republic | 1h 02m New York | JFK 15:00 → ORD 17:11DL 4783 · flown by Endeavor | 5h 42m | 45% | 23% |
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 2670 BWI 06:15 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details → |
3h 42m | 7h 20m | 98% | 94% |
| Southwest WN 883 BWI 06:38 → BOS American AA 3022 BOS 10:29 → ORD Connection details → |
2h 21m | 6h 51m | 100% | 91% |
| Delta DL 3826 IAD 06:00 → DTW American AA 4103 DTW 10:33 → ORD Connection details → |
2h 53m | 6h 08m | 96% | 91% |
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