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

No nonstop, and no clear pattern: the best connection reaches Chicago on time 3 times in 4.

Best connections, any airlines

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.


Southwest + Unitedtwo ticketsDetails →	HOU 05:00 → MCO 08:25WN 4483	2h 27m Orlando	MCO 10:52 → ORD 13:02UA 2466	8h 02m	100%	92%
Southwest + Americantwo ticketsDetails →	HOU 05:30 → LAS 06:30WN 2251	3h 10m Las Vegas	LAS 09:40 → ORD 15:42AA 2020	10h 12m	100%	90%
Southwest + Americantwo ticketsDetails →	HOU 07:50 → MSY 09:00WN 1796	3h 35m New Orleans	MSY 12:35 → ORD 15:21AA 4748 · flown by Republic	7h 31m	100%	86%
Southwest + Unitedtwo ticketsDetails →	HOU 05:30 → DEN 06:55WN 1970	2h 40m Denver	DEN 09:35 → ORD 13:15UA 2329	7h 45m	100%	83%
Southwest + Unitedtwo ticketsDetails →	HOU 05:50 → ATL 08:50WN 2622	2h 39m Atlanta	ATL 11:29 → ORD 12:52UA 1239	7h 02m	100%	82%
Southwest + Unitedtwo ticketsDetails →	HOU 07:15 → TPA 10:28WN 2088	2h 02m Tampa	TPA 12:30 → ORD 14:40UA 2223	7h 25m	98%	82%
Southwest + Unitedtwo ticketsDetails →	HOU 07:10 → MCO 10:35WN 4183	1h 59m Orlando	MCO 12:34 → ORD 14:42UA 2475	7h 32m	98%	80%
Southwest + Unitedtwo ticketsDetails →	HOU 07:10 → BNA 09:10WN 1954	2h 05m Nashville	BNA 11:15 → ORD 13:15UA 4653 · flown by SkyWest	6h 05m	96%	78%
Tight connection: often missed
American Details →	HOU 16:14 → DFW 17:38AA 5002 · flown by SkyWest	1h 00m Dallas-Fort Worth	DFW 18:38 → ORD 21:22AA 1424	5h 08m	60%	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

DFW · 1h 00m · leaves 06:03 12%

Afternoon and evening

ATL · 1h 03m · leaves 13:10 20%

DFW · 1h 00m · leaves 16:14 40%

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