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 77% on time.

Nonstops


Southwest	LAS	MDW	3h 30m	77%	0.7%	2,298	Flying now
Allegiant	LAS	MDW	–	50%few flights	0.0%	2	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 2 h ahead of Las Vegas). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	LAS 20:35 → TUL 01:15WN 4339	3h 45m Tulsa	TUL 05:00 → MDW 06:45 +1WN 4057	8h 10m	100%	97%
Southwest Details →	LAS 21:05 → OKC 01:32WN 4160	3h 28m Oklahoma City	OKC 05:00 → MDW 06:55 +1WN 3121	7h 50m	96%	94%
Southwest Details →	LAS 20:25 → MKE 01:55WN 4136	3h 50m Milwaukee	MKE 05:45 → MDW 06:35 +1WN 3178	8h 10m	96%	94%
Southwest Details →	LAS 21:05 → OMA 01:45WN 4587	3h 40m Omaha	OMA 05:25 → MDW 06:50 +1WN 4504	7h 45m	98%	94%
Southwest Details →	LAS 20:55 → MCI 01:42WN 2267	3h 33m Kansas City	MCI 05:15 → MDW 06:40 +1WN 4276	7h 45m	100%	93%
Southwest Details →	LAS 22:50 → MCO 06:25WN 4590	1h 35m Orlando	MCO 08:00 → MDW 09:50 +1WN 2835	9h 00m	98%	92%
Southwest Details →	LAS 18:30 → SMF 20:05WN 4032	3h 45m Sacramento	SMF 23:50 → MDW 05:45 +1WN 3802	9h 15m	100%	89%
Southwest Details →	LAS 20:20 → STL 01:55WN 2371	3h 45m St Louis	STL 05:40 → MDW 06:45 +1WN 1008	8h 25m	100%	88%
Tight connection: often missed
Southwest Details →	LAS 21:10 → SMF 22:45WN 2362	1h 05m Sacramento	SMF 23:50 → MDW 05:45 +1WN 3802	6h 35m	55%	48%
Southwest Details →	LAS 20:05 → SFO 21:35WN 4397	2h 05m San Francisco	SFO 23:40 → MDW 05:55 +1WN 3649	7h 50m	74%	30%
Southwest Details →	LAS 14:52 → BNA 20:30WN 4395	1h 10m Nashville	BNA 21:40 → MDW 19:10WN 578	6h 18m	52%	22%

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

SEA · 1h 20m · leaves 07:40 10%

MCO · 1h 00m · leaves 22:50 17%

Afternoon and evening

SMF · 1h 05m · leaves 21:10 45%

BNA · 1h 10m · leaves 14:52 48%

DEN · 1h 00m · leaves 15:00 57%

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 2794 LAS 22:14 → CVG Southwest WN 3016 CVG 08:00 → MDW Connection details →	3h 00m	7h 51m	98%	95%
Frontier F9 2016 LAS 00:59 → DEN Southwest WN 114 DEN 07:10 → MDW Connection details →	3h 17m	7h 31m	95%	89%
Delta DL 857 LAS 00:33 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	2h 42m	8h 27m	97%	86%

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