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

Take the nonstop: Southwest CVG → MDW (1h 10m) reaches Chicago on time 4 times in 5; the most reliable connection, Delta via Detroit (3h 55m), 69%.

Nonstops (seasonal or thin)


Southwest	CVG	MDW	1h 10m	82%	1.1%	538	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 Hebron). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	CVG 07:00 → BNA 07:10WN 3349	2h 10m Nashville	BNA 09:20 → MDW 11:00WN 1473	5h 00m	100%	88%
Delta Details →	CVG 07:05 → ATL 08:39DL 2302	2h 26m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 00m	99%	84%
Delta Details →	CVG 05:34 → ATL 07:04DL 2441	2h 05m Atlanta	ATL 09:09 → MDW 10:09DL 1063	5h 35m	99%	84%
Delta Details →	CVG 08:14 → DTW 09:30DL 5479 · flown by Endeavor	2h 55m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	5h 32m	97%	78%
Delta Details →	CVG 16:26 → ATL 18:00DL 3169	3h 15m Atlanta	ATL 21:15 → MDW 22:17DL 1076	6h 51m	98%	74%
Delta Details →	CVG 10:05 → ATL 11:35DL 963	3h 40m Atlanta	ATL 15:15 → MDW 16:15DL 1728	7h 10m	100%	71%
Delta Details →	CVG 06:19 → DTW 07:36DL 5307 · flown by Endeavor	1h 14m Detroit	DTW 08:50 → MDW 09:14DL 4684 · flown by Endeavor	3h 55m	94%	69%
Southwest Details →	CVG 05:35 → BWI 07:05WN 1246	2h 30m Baltimore	BWI 09:35 → MDW 10:35WN 4217	6h 00m	100%	68%
Tight connection: often missed
Delta Details →	CVG 16:00 → DTW 17:17DL 5456 · flown by Endeavor	50m Detroit	DTW 18:07 → MDW 18:25DL 4677 · flown by Endeavor	3h 29m	61%	36%
Southwest Details →	CVG 15:50 → BWI 17:15WN 1247	1h 15m Baltimore	BWI 18:30 → MDW 19:35WN 998	4h 45m	73%	34%

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 20m · leaves 08:15 5%

DTW · 1h 14m · leaves 06:19 6%

Afternoon and evening

BNA · 1h 20m · leaves 18:55 19%

BWI · 1h 15m · leaves 15:50 27%

DTW · 50m · leaves 16:00 39%

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 2441 CVG 05:34 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	2h 56m	6h 26m	99%	88%
American AA 2967 CVG 07:42 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	2h 19m	5h 53m	95%	87%
Delta DL 5229 CVG 07:00 → DCA Southwest WN 1445 DCA 12:00 → MDW Connection details →	3h 27m	7h 00m	98%	82%

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