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 3 in 4 on time.

Nonstops


Southwest	DEN	MDW	2h 20m	75%	1.6%	2,151	Flying now
Frontier	DEN	MDW	2h 25m	78%	1.4%	74	Not 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 ahead of Denver). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	DEN 05:00 → AUS 08:05WN 411	2h 20m Austin	AUS 10:25 → MDW 12:55WN 4077	6h 55m	100%	88%
Southwest Details →	DEN 12:55 → SDF 17:25WN 1712	2h 40m Louisville	SDF 20:05 → MDW 20:20WN 3329	6h 25m	100%	85%
Southwest Details →	DEN 07:45 → MCI 10:25WN 1584	1h 13m Kansas City	MCI 11:38 → MDW 13:02WN 2571	4h 18m	99%	79%
Southwest Details →	DEN 05:10 → DAL 08:05WN 1078	2h 00m Dallas	DAL 10:05 → MDW 12:20WN 1357	6h 10m	100%	79%
Southwest Details →	DEN 11:25 → ICT 13:50WN 4262	2h 05m Wichita	ICT 15:55 → MDW 17:55WN 1276	5h 30m	95%	78%
Delta Details →	DEN 06:05 → DTW 10:57DL 1745	1h 28m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	5h 41m	96%	78%
Southwest Details →	DEN 05:45 → LAS 06:40WN 3106	1h 40m Las Vegas	LAS 08:20 → MDW 13:55WN 2271	7h 10m	100%	75%
Delta Details →	DEN 07:15 → ATL 12:12DL 431	3h 03m Atlanta	ATL 15:15 → MDW 16:15DL 1728	8h 00m	99%	73%
Tight connection: often missed
Southwest Details →	DEN 21:15 → ONT 22:35WN 1663	1h 20m Ontario	ONT 23:55 → MDW 05:40 +1WN 3153	7h 25m	65%	54%
Southwest Details →	DEN 23:50 → BWI 05:15WN 1501	55m Baltimore	BWI 06:10 → MDW 07:10 +1WN 995	6h 20m	55%	49%
Southwest Details →	DEN 21:05 → LAX 22:40WN 3110	1h 15m Los Angeles	LAX 23:55 → MDW 05:55 +1WN 2413	7h 50m	56%	47%

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

MCI · 1h 13m · leaves 07:45 1%

SJC · 1h 15m · leaves 07:50 6%

DAL · 55m · leaves 06:15 16%

Afternoon and evening

LAS · 50m · leaves 17:30 66%

CMH · 48m · leaves 14:40 67%

DAL · 50m · leaves 15:55 77%

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.


American AA 3156 DEN 23:59 → CLT Southwest WN 3048 CLT 07:35 → MDW Connection details →	2h 22m	7h 41m	93%	82%
Delta DL 1096 DEN 00:59 → DTW Southwest WN 1781 DTW 08:40 → MDW Connection details →	2h 52m	6h 56m	97%	81%
United UA 5497 DEN 09:55 → ICT Southwest WN 1276 ICT 15:55 → MDW Connection details →	3h 28m	7h 00m	99%	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