Itineraries flown on 20+ days in the Jun 6 – Jul 31, 2026 schedule · each leg’s record Aug 2025 – Jul 2026

No clear winner: Southwest’s MDW → CLE flights land within a few points of 4 in 5 on time whatever the hour.

Nonstops


Southwest	MDW	CLE	1h 15m	81%	1.4%	1,109	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

Ranked by chance you reach Cleveland on time. Total trip = scheduled departure to arrival, layover included (Cleveland is 1 h ahead of Chicago). Layovers up to 4 hours. Pick a connection for the details.


Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 57m Atlanta	ATL 11:52 → CLE 13:38DL 775	6h 38m	96%	80%
Delta Details →	MDW 09:17 → DTW 11:35DL 4674 · flown by Endeavor	2h 44m Detroit	DTW 14:19 → CLE 15:17DL 3581 · flown by SkyWest	5h 00m	98%	78%
Delta Details →	MDW 11:05 → ATL 14:01DL 1063	1h 25m Atlanta	ATL 15:26 → CLE 17:17DL 880	5h 12m	94%	75%
Delta Details →	MDW 17:10 → ATL 20:22DL 1728	2h 27m Atlanta	ATL 22:49 → CLE 00:41 +1DL 1320	6h 31m	95%	71%
Southwest Details →	MDW 07:15 → BNA 08:40WN 2959	1h 25m Nashville	BNA 10:05 → CLE 12:35WN 4571	4h 20m	85%	71%
Southwest Details →	MDW 07:00 → BWI 09:45WN 2742	1h 25m Baltimore	BWI 11:10 → CLE 12:30WN 1031	4h 30m	94%	70%
Southwest Details →	MDW 07:50 → STL 09:10WN 2900	3h 40m St Louis	STL 12:50 → CLE 15:20WN 3899	6h 30m	100%	67%
Delta Details →	MDW 12:50 → ATL 15:49DL 2417	1h 05m Atlanta	ATL 16:54 → CLE 18:44DL 1350	4h 54m	87%	65%
Tight connection: often missed
Southwest Details →	MDW 09:55 → DEN 11:30WN 2654	50m Denver	DEN 12:20 → CLE 17:10WN 1506	6h 15m	56%	46%

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.

Morning

ATL · 48m · leaves 06:00 15%

DTW · 1h 11m · leaves 09:17 16%

STL · 1h 05m · leaves 10:32 21%

Afternoon and evening

ATL · 1h 05m · leaves 12:50 13%

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

One ticketMiss it and the airline rebooks you; bags go through. 45 min is enough.

Separate ticketsMiss it and you buy a new ticket. Re-check bags, clear security again: we require 90 min.


Southwest WN 3054 MDW 07:15 → ATL Delta DL 2545 ATL 13:36 → CLE Connection details →	3h 31m	7h 08m	100%	87%
Southwest WN 1405 MDW 09:10 → BOS Delta DL 5641 BOS 14:54 → CLE Connection details →	2h 26m	6h 56m	100%	85%
Southwest WN 4154 MDW 08:55 → ATL Delta DL 880 ATL 15:26 → CLE Connection details →	3h 41m	7h 22m	100%	83%

Rank all connections, any airlines →

Regional partners count as the airline that sells them: SkyWest flying Delta Connection is one Delta ticket.

How these are worked out. Makes the connection: share of the last year’s flights where the first flight arrived with at least 45 minutes to spare (90 on separate tickets). Arrives on time: first flight not cancelled × connection made × second flight not cancelled and arriving within 15 minutes. Not yet counted: the second flight also leaving late (which helps), gate-to-gate distance at the hub, and rebooking after a missed connection.

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