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 73% on time.

Nonstops


American	MSN	ORD	1h 13m	75%	4.2%	2,026	Flying now
United	MSN	ORD	1h 11m	71%	3.5%	2,708	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. Layovers up to 4 hours. Pick a connection for the details.


Delta Details →	MSN 07:00 → DTW 09:22DL 3665 · flown by SkyWest	53m Detroit	DTW 10:15 → ORD 10:50DL 3673 · flown by SkyWest	3h 50m	100%	90%
United Details →	MSN 05:00 → DEN 06:42UA 5545 · flown by SkyWest	58m Denver	DEN 07:40 → ORD 11:23UA 1928	6h 23m	96%	88%
American Details →	MSN 07:20 → BOS 10:53AA 4687 · flown by Republic	1h 08m Boston	BOS 12:01 → ORD 14:02AA 1610	6h 42m	93%	82%
United Details →	MSN 06:29 → EWR 09:50UA 3482 · flown by Republic	1h 35m Newark	EWR 11:25 → ORD 13:08UA 1875	6h 39m	94%	70%
United Details →	MSN 08:50 → DEN 10:20UA 2360	55m Denver	DEN 11:15 → ORD 14:55UA 2865	6h 05m	86%	70%
Delta Details →	MSN 07:00 → DTW 09:25DL 4765 · flown by Endeavor	3h 10m Detroit	DTW 12:35 → ORD 13:03DL 1716	6h 03m	97%	70%
American Details →	MSN 06:00 → PHL 09:19AA 5509 · flown by PSA	1h 16m Philadelphia	PHL 10:35 → ORD 12:09AA 1041	6h 09m	92%	68%
American Details →	MSN 07:00 → CLT 10:16AA 1002	2h 49m Charlotte	CLT 13:05 → ORD 14:20AA 836	7h 20m	99%	68%
Tight connection: often missed
American Details →	MSN 13:17 → PHL 16:33AA 5471 · flown by PSA	1h 07m Philadelphia	PHL 17:40 → ORD 19:26AA 1012	6h 09m	70%	36%
American Details →	MSN 17:11 → DFW 19:46AA 2141	1h 14m Dallas-Fort Worth	DFW 21:00 → ORD 23:39AA 2346	6h 28m	61%	35%
American Details →	MSN 16:11 → CLT 19:40AA 5307 · flown by PSA	47m Charlotte	CLT 20:27 → ORD 22:00AA 627	5h 49m	50%	28%

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 18m · leaves 05:00 1%

BOS · 1h 08m · leaves 07:20 7%

LGA · 1h 10m · leaves 07:00 8%

Afternoon and evening

DCA · 1h 02m · leaves 13:07 32%

DFW · 1h 14m · leaves 17:11 39%

CLT · 47m · leaves 16:11 50%

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 1274 MSN 06:00 → MSP American AA 4162 MSP 10:31 → ORD Connection details →	3h 22m	6h 16m	97%	85%
Delta DL 3665 MSN 07:00 → DTW American AA 3498 DTW 13:02 → ORD Connection details →	3h 40m	6h 36m	100%	80%
Delta DL 4103 MSN 08:52 → MSP American AA 3432 MSP 13:57 → ORD Connection details →	3h 42m	6h 50m	98%	78%

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