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

No clear winner: Frontier’s IAH → MDW flights land within a few points of 3 in 4 on time whatever the hour.

Nonstops (none in the current schedule)


Frontier	IAH	MDW	2h 37m	75%	1.8%	113	Not flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

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


American + Southwesttwo ticketsDetails →	IAH 06:01 → CLT 09:43AA 2011	1h 52m Charlotte	CLT 11:35 → MDW 12:35WN 4529	6h 34m	92%	87%
United + Southwesttwo ticketsDetails →	IAH 05:15 → DEN 06:47UA 1874	3h 13m Denver	DEN 10:00 → MDW 13:25WN 755	8h 10m	97%	84%
Delta Details →	IAH 05:40 → ATL 08:43DL 1069	2h 22m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 25m	99%	83%
United + Southwesttwo ticketsDetails →	IAH 07:35 → AUS 08:39UA 2016	1h 46m Austin	AUS 10:25 → MDW 12:55WN 4077	5h 20m	92%	81%
United + Southwesttwo ticketsDetails →	IAH 19:53 → PHX 20:42UA 2078	3h 13m Phoenix	PHX 23:55 → MDW 05:10 +1WN 3298	9h 17m	97%	80%
United + Southwesttwo ticketsDetails →	IAH 19:50 → LAX 21:26UA 483	2h 29m Los Angeles	LAX 23:55 → MDW 05:55 +1WN 2413	10h 05m	95%	80%
Delta Details →	IAH 05:20 → DTW 09:11DL 1389	3h 14m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	7h 26m	99%	79%
United + Southwesttwo ticketsDetails →	IAH 07:40 → BNA 09:47UA 2174	3h 08m Nashville	BNA 12:55 → MDW 14:30WN 1430	6h 50m	99%	77%
Tight connection: often missed
Delta Details →	IAH 16:51 → ATL 20:13DL 2890	1h 02m Atlanta	ATL 21:15 → MDW 22:17DL 1076	5h 26m	59%	45%

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

ATL · 1h 00m · leaves 07:02 12%

Afternoon and evening

ATL · 1h 02m · leaves 16:51 41%

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