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 9 in 10 on time.

Nonstops (seasonal or thin)


American	ORD	BIL	3h 10m	90%	0.4%	230	Flying now
United	ORD	BIL	3h 21m	86%	0.0%	86	Not flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

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


United + Alaskatwo ticketsDetails →	ORD 07:00 → PDX 09:34UA 2300	2h 39m Portland	PDX 12:13 → BIL 15:03AS 2368 · flown by Horizon	9h 03m	99%	93%
American + Deltatwo ticketsDetails →	ORD 10:05 → SLC 12:35AA 2616	3h 58m Salt Lake City	SLC 16:33 → BIL 18:00DL 3828 · flown by SkyWest	8h 55m	100%	89%
United Details →	ORD 05:00 → DEN 06:42UA 2666	1h 13m Denver	DEN 07:55 → BIL 09:36UA 4762 · flown by SkyWest	5h 36m	99%	85%
Alaska Details →	ORD 15:43 → SEA 18:22AS 407	2h 37m Seattle	SEA 20:59 → BIL 23:51AS 2457 · flown by Horizon	9h 08m	95%	85%
American Details →	ORD 05:00 → DFW 07:30AA 760	3h 30m Dallas-Fort Worth	DFW 11:00 → BIL 12:59AA 3429 · flown by Envoy	8h 59m	99%	84%
United Details →	ORD 08:40 → DEN 10:31UA 526	3h 14m Denver	DEN 13:45 → BIL 15:29UA 5845 · flown by SkyWest	7h 49m	100%	83%
American + Unitedtwo ticketsDetails →	ORD 06:41 → DEN 08:24AA 1747	3h 21m Denver	DEN 11:45 → BIL 13:22UA 703	7h 41m	99%	79%
Alaska Details →	ORD 06:00 → SEA 08:38AS 715	1h 31m Seattle	SEA 10:09 → BIL 13:05AS 2054 · flown by Horizon	8h 05m	93%	74%
Tight connection: often missed
United Details →	ORD 16:12 → DEN 18:13UA 2769	1h 27m Denver	DEN 19:40 → BIL 21:17UA 1417	6h 05m	71%	56%
American Details →	ORD 16:51 → DFW 19:28AA 2988	1h 47m Dallas-Fort Worth	DFW 21:15 → BIL 23:13AA 3937 · flown by Envoy	7h 22m	72%	53%
United Details →	ORD 18:17 → DEN 20:22UA 1974	48m Denver	DEN 21:10 → BIL 22:54UA 5257 · flown by SkyWest	5h 37m	47%	37%

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

DEN · 1h 13m · leaves 05:00 1%

Afternoon and evening

DEN · 48m · leaves 18:17 53%

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