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 → CVG flights land within a few points of 3 in 4 on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	MDW	CVG	1h 10m	74%	2.0%	538	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

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


Southwest + Deltatwo ticketsDetails →	MDW 07:40 → MSP 09:10WN 1243	3h 40m Minneapolis	MSP 12:50 → CVG 15:40DL 3113	7h 00m	100%	86%
Southwest + Deltatwo ticketsDetails →	MDW 07:55 → DTW 10:05WN 1775	3h 55m Detroit	DTW 14:00 → CVG 15:16DL 5446 · flown by Endeavor	6h 21m	100%	83%
Southwest + Frontiertwo ticketsDetails →	MDW 05:10 → MCO 08:40WN 2815	2h 27m Orlando	MCO 11:07 → CVG 13:25F9 1565	7h 15m	100%	82%
Southwest + Deltatwo ticketsDetails →	MDW 07:15 → ATL 10:05WN 3054	3h 44m Atlanta	ATL 13:49 → CVG 15:13DL 3169	6h 58m	100%	79%
Southwest + Deltatwo ticketsDetails →	MDW 08:55 → ATL 11:45WN 4154	3h 30m Atlanta	ATL 15:15 → CVG 16:42DL 1008	6h 47m	100%	79%
Southwest Details →	MDW 08:55 → BWI 11:45WN 1355	3h 35m Baltimore	BWI 15:20 → CVG 16:55WN 760	7h 00m	100%	79%
Southwest + Deltatwo ticketsDetails →	MDW 05:15 → LGA 08:15WN 2801	2h 30m New York	LGA 10:45 → CVG 12:51DL 4987 · flown by Endeavor	6h 38m	100%	78%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 15m Atlanta	ATL 11:10 → CVG 12:34DL 3149	5h 37m	95%	78%
Tight connection: often missed
Delta Details →	MDW 13:26 → DTW 15:44DL 4688 · flown by Endeavor	48m Detroit	DTW 16:32 → CVG 17:49DL 5060 · flown by Endeavor	3h 23m	73%	54%
Frontier Details →	MDW 06:00 → ATL 09:19F9 2292	55m Atlanta	ATL 10:14 → CVG 11:47F9 4771	4h 46m	64%	45%
Southwest Details →	MDW 19:00 → BWI 21:55WN 2745	50m Baltimore	BWI 22:45 → CVG 00:30 +1WN 4435	4h 25m	39%	26%

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

MSP · 1h 15m · leaves 09:54 9%

ATL · 1h 04m · leaves 06:00 9%

Afternoon and evening

DTW · 48m · leaves 13:26 27%

BWI · 50m · leaves 19:00 61%

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.

The table above includes two-ticket connections (marked “two tickets”), held to the 90-minute minimum. One ticket only →

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