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

No clear winner: airlines and hours on this route all land within a few points of 4 in 5 on time.

Nonstops


Southwest	MDW	TPA	2h 35m	78%	1.4%	1,536	Flying now
Frontier	MDW	TPA	2h 36m	91%	2.2%	45	Not flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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


Southwest Details →	MDW 07:50 → STL 09:10WN 2900	55m St Louis	STL 10:05 → TPA 13:25WN 3986	4h 35m	93%	85%
Southwest Details →	MDW 07:40 → RDU 10:35WN 852	2h 45m Raleigh/Durham	RDU 13:20 → TPA 15:15WN 4442	6h 35m	100%	82%
Southwest Details →	MDW 05:20 → AUS 07:50WN 2726	50m Austin	AUS 08:40 → TPA 12:05WN 411	5h 45m	90%	80%
Delta Details →	MDW 09:54 → MSP 11:35DL 5469 · flown by Endeavor	1h 44m Minneapolis	MSP 13:19 → TPA 17:32DL 2264	6h 38m	98%	80%
Delta Details →	MDW 09:17 → DTW 11:35DL 4674 · flown by Endeavor	2h 30m Detroit	DTW 14:05 → TPA 16:47DL 1243	6h 30m	96%	78%
Southwest Details →	MDW 06:50 → DEN 08:20WN 2765	1h 45m Denver	DEN 10:05 → TPA 15:45WN 3560	7h 55m	100%	78%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 19m Atlanta	ATL 11:14 → TPA 12:45DL 1099	5h 45m	95%	77%
Southwest Details →	MDW 07:15 → BNA 08:40WN 2959	3h 10m Nashville	BNA 11:50 → TPA 14:40WN 684	6h 25m	100%	72%
Tight connection: often missed
Southwest Details →	MDW 16:15 → DEN 18:00WN 2769	1h 15m Denver	DEN 19:15 → TPA 00:55 +1WN 2232	7h 35m	73%	29%
Southwest Details →	MDW 18:00 → STL 19:10WN 2904	50m St Louis	STL 20:00 → TPA 23:18WN 4619	4h 20m	57%	28%
Southwest Details →	MDW 14:40 → ATL 17:35WN 4592	55m Atlanta	ATL 18:30 → TPA 20:05WN 245	4h 25m	31%	13%

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

STL · 55m · leaves 07:50 7%

ATL · 1h 05m · leaves 06:00 9%

AUS · 50m · leaves 05:20 10%

Afternoon and evening

DAL · 1h 10m · leaves 16:20 38%

STL · 50m · leaves 18:00 43%

ATL · 55m · leaves 14:40 69%

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 2727 MDW 09:48 → AUS Delta DL 3734 AUS 14:55 → TPA Connection details →	2h 33m	8h 13m	100%	82%
Southwest WN 1775 MDW 07:55 → DTW Delta DL 1243 DTW 14:05 → TPA Connection details →	4h 00m	7h 52m	100%	81%
Southwest WN 3054 MDW 07:15 → ATL Delta DL 1525 ATL 12:46 → TPA Connection details →	2h 41m	5h 57m	100%	79%

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