Connect in the morning. The same one-hour layover misses 5% of the time at 7 am and 37% of the time at 8 pm.
Nonstops
Nonstop details →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 Cleveland). Layovers up to 4 hours. Pick a connection for the details.
| UnitedDetails → | CLE 06:00 → IAD 07:15UA 1252 | 3h 16m Dulles | IAD 10:31 → ORD 11:53UA 1252 | 6h 53m | 100% | 91% |
| DeltaDetails → | CLE 06:30 → DTW 07:31DL 3532 · flown by SkyWest | 2h 44m Detroit | DTW 10:15 → ORD 10:50DL 3673 · flown by SkyWest | 5h 20m | 93% | 83% |
| AmericanDetails → | CLE 05:01 → CLT 06:42AA 2632 | 1h 04m Charlotte | CLT 07:46 → ORD 09:02AA 2843 | 5h 01m | 95% | 81% |
| UnitedDetails → | CLE 06:26 → IAH 08:25UA 756 | 1h 10m Houston | IAH 09:35 → ORD 12:29UA 2124 | 7h 03m | 94% | 80% |
| UnitedDetails → | CLE 10:37 → IAD 11:53UA 445 | 1h 22m Dulles | IAD 13:15 → ORD 14:29UA 2331 | 4h 52m | 96% | 77% |
| AmericanDetails → | CLE 08:46 → DCA 10:09AA 4737 · flown by Republic | 1h 26m Washington | DCA 11:35 → ORD 12:53AA 489 | 5h 07m | 95% | 77% |
| AmericanDetails → | CLE 08:06 → CLT 09:50AA 2021 | 1h 11m Charlotte | CLT 11:01 → ORD 12:19AA 2908 | 5h 13m | 88% | 76% |
| UnitedDetails → | CLE 08:55 → DEN 10:10UA 690 | 1h 05m Denver | DEN 11:15 → ORD 14:55UA 2865 | 7h 00m | 93% | 76% |
| Tight connection: often missed | ||||||
| AmericanDetails → | CLE 15:03 → PHL 16:43AA 5861 · flown by Piedmont | 57m Philadelphia | PHL 17:40 → ORD 19:26AA 1012 | 5h 23m | 63% | 33% |
| DeltaDetails → | CLE 17:46 → BOS 19:55DL 5641 · flown by Republic | 50m Boston | BOS 20:45 → ORD 22:39DL 2804 | 5h 56m | 63% | 27% |
| AmericanDetails → | CLE 14:35 → DFW 16:35AA 2818 | 1h 00m Dallas-Fort Worth | DFW 17:35 → ORD 20:29AA 1893 | 6h 55m | 65% | 25% |
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
| Southwest WN 1153 CLE 06:00 → BWI United UA 704 BWI 10:32 → ORD Connection details → |
3h 12m | 6h 48m | 100% | 90% |
| Southwest WN 4568 CLE 06:40 → BNA American AA 3973 BNA 09:04 → ORD Connection details → |
1h 54m | 5h 20m | 100% | 90% |
| Delta DL 3532 CLE 06:30 → DTW American AA 4103 DTW 10:33 → ORD Connection details → |
3h 02m | 5h 38m | 93% | 88% |
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