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

Connect in the morning. The same one-hour layover misses 1 time in 5 at 9 am and 43% of the time at 8 pm.

Nonstops


Southwest	CLE	MDW	1h 20m	84%	1.1%	1,110	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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.


Southwest Details →	CLE 06:40 → BNA 07:10WN 4568	2h 10m Nashville	BNA 09:20 → MDW 11:00WN 1473	5h 20m	100%	88%
Delta Details →	CLE 07:05 → ATL 08:55DL 2838	2h 10m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 00m	99%	83%
Southwest Details →	CLE 07:05 → STL 07:40WN 1165	1h 15m St Louis	STL 08:55 → MDW 10:00WN 2570	3h 55m	93%	82%
Delta Details →	CLE 05:35 → ATL 07:22DL 2734	1h 47m Atlanta	ATL 09:09 → MDW 10:09DL 1063	5h 34m	96%	81%
Delta Details →	CLE 08:18 → DTW 09:20DL 3817 · flown by SkyWest	3h 05m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	5h 28m	96%	78%
Delta Details →	CLE 16:28 → ATL 18:22DL 2545	2h 53m Atlanta	ATL 21:15 → MDW 22:17DL 1076	6h 49m	98%	73%
Delta Details →	CLE 10:20 → ATL 12:07DL 1500	3h 08m Atlanta	ATL 15:15 → MDW 16:15DL 1728	6h 55m	98%	72%
Southwest Details →	CLE 06:00 → BWI 07:20WN 1153	2h 15m Baltimore	BWI 09:35 → MDW 10:35WN 4217	5h 35m	100%	68%
Tight connection: often missed
Frontier Details →	CLE 17:51 → ATL 20:06F9 4209	54m Atlanta	ATL 21:00 → MDW 22:03F9 2291	5h 13m	57%	37%
Southwest Details →	CLE 18:30 → DEN 19:40WN 2887	1h 10m Denver	DEN 20:50 → MDW 00:15 +1WN 1615	6h 42m	65%	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.

Morning

ATL · 1h 10m · leaves 08:05 6%

STL · 1h 15m · leaves 07:05 7%

DTW · 1h 19m · leaves 06:30 12%

Afternoon and evening

DTW · 1h 05m · leaves 16:00 19%

DEN · 1h 10m · leaves 18:30 35%

ATL · 54m · leaves 17:51 43%

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.


Delta DL 2734 CLE 05:35 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	2h 38m	6h 25m	96%	85%
American AA 4737 CLE 08:46 → DCA Southwest WN 1445 DCA 12:00 → MDW Connection details →	1h 51m	5h 14m	95%	81%
American AA 2021 CLE 08:06 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	1h 45m	5h 29m	86%	81%

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