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	MDW	DEN	2h 40m	75%	1.3%	2,198	Flying now
Frontier	MDW	DEN	2h 48m	68%	1.4%	73	Not flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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


Southwest Details →	MDW 07:45 → CMH 10:05WN 4093	2h 10m Columbus	CMH 12:15 → DEN 13:15WN 779	6h 30m	100%	88%
Southwest Details →	MDW 08:00 → MCI 09:30WN 2808	1h 10m Kansas City	MCI 10:40 → DEN 11:25WN 2548	4h 25m	100%	81%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 50m Atlanta	ATL 11:45 → DEN 12:59DL 706	7h 59m	95%	80%
Southwest Details →	MDW 05:20 → PHX 06:55WN 2858	1h 55m Phoenix	PHX 08:50 → DEN 11:35WN 3261	7h 15m	100%	80%
Delta Details →	MDW 09:54 → MSP 11:35DL 5469 · flown by Endeavor	2h 52m Minneapolis	MSP 14:27 → DEN 15:38DL 1025	6h 44m	98%	79%
Southwest Details →	MDW 07:45 → SDF 10:05WN 1267	3h 05m Louisville	SDF 13:10 → DEN 13:55WN 1297	7h 10m	100%	79%
Southwest Details →	MDW 07:10 → PHX 08:45WN 2520	2h 15m Phoenix	PHX 11:00 → DEN 13:45WN 3262	7h 35m	100%	78%
Southwest Details →	MDW 10:10 → DSM 11:30WN 1771	2h 00m Des Moines	DSM 13:30 → DEN 14:25WN 1770	5h 15m	100%	73%
Tight connection: often missed
Southwest Details →	MDW 10:05 → OAK 12:35WN 3366	50m Oakland	OAK 13:25 → DEN 16:50WN 3043	7h 45m	62%	24%
Southwest Details →	MDW 10:08 → SAN 12:15WN 4648	1h 05m San Diego	SAN 13:20 → DEN 16:55WN 3496	7h 42m	66%	16%
Southwest Details →	MDW 12:55 → LGA 16:00WN 2803	50m New York	LGA 16:50 → DEN 19:30WN 2456	7h 35m	32%	11%

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

BWI · 1h 05m · leaves 08:55 5%

HOU · 1h 05m · leaves 06:40 10%

ATL · 55m · leaves 06:00 10%

Afternoon and evening

MCO · 55m · leaves 13:40 47%

HOU · 50m · leaves 19:15 56%

LGA · 50m · leaves 12:55 68%

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 1243 MDW 07:40 → MSP United UA 2232 MSP 11:34 → DEN Connection details →	2h 24m	6h 05m	100%	94%
Southwest WN 2726 MDW 05:20 → AUS United UA 779 AUS 11:27 → DEN Connection details →	3h 37m	8h 25m	100%	91%
Southwest WN 3054 MDW 07:15 → ATL Delta DL 957 ATL 12:50 → DEN Connection details →	2h 45m	7h 49m	100%	89%

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