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

No clear winner: Southwest’s GRR → MDW flights land within a few points of 4 in 5 on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	GRR	MDW	1h 05m	79%	0.4%	931	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 1 h behind Grand Rapids). Layovers up to 4 hours. Pick a connection for the details.


Delta Details →	GRR 06:10 → ATL 08:14DL 2453	2h 51m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 55m	99%	84%
Delta Details →	GRR 08:15 → DTW 09:19DL 3885 · flown by SkyWest	3h 06m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	5h 31m	100%	81%
Delta Details →	GRR 05:30 → DTW 06:30DL 4885 · flown by Endeavor	2h 20m Detroit	DTW 08:50 → MDW 09:14DL 4684 · flown by Endeavor	4h 44m	95%	70%
Southwest Details →	GRR 05:25 → BWI 07:05WN 1891	2h 30m Baltimore	BWI 09:35 → MDW 10:35WN 4217	6h 10m	96%	62%
Southwest Details →	GRR 14:45 → BWI 16:25WN 1892	2h 35m Baltimore	BWI 19:00 → MDW 20:05WN 1005	6h 20m	95%	59%
Delta Details →	GRR 07:00 → MSP 07:33DL 2913	3h 57m Minneapolis	MSP 11:30 → MDW 13:09DL 4820 · flown by Endeavor	7h 09m	98%	57%
Delta Details →	GRR 14:35 → DTW 15:38DL 5390 · flown by Endeavor	2h 29m Detroit	DTW 18:07 → MDW 18:25DL 4677 · flown by Endeavor	4h 54m	90%	53%
Tight connection: often missed
Delta Details →	GRR 10:34 → DTW 11:35DL 3500 · flown by SkyWest	50m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	3h 12m	74%	60%
Southwest Details →	GRR 15:45 → DEN 16:35WN 1893	1h 00m Denver	DEN 17:35 → MDW 21:00WN 1604	6h 15m	59%	16%

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 · 55m · leaves 06:10 12%

DTW · 50m · leaves 10:34 26%

Afternoon and evening

DEN · 1h 00m · leaves 15:45 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.


Delta DL 2453 GRR 06:10 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	1h 46m	5h 50m	91%	80%
American AA 5494 GRR 06:44 → PHL Southwest WN 3224 PHL 11:22 → MDW Connection details →	2h 38m	6h 48m	98%	78%
Delta DL 2913 GRR 07:00 → MSP Southwest WN 4345 MSP 10:25 → MDW Connection details →	2h 52m	5h 55m	96%	76%

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