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 MDW → GRR flights land within a few points of 3 in 4 on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	MDW	GRR	55m	76%	0.9%	931	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

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


Delta Details →	MDW 13:26 → DTW 15:44DL 4688 · flown by Endeavor	2h 16m Detroit	DTW 18:00 → GRR 19:01DL 5800 · flown by Republic	4h 35m	93%	85%
Southwest + Deltatwo ticketsDetails →	MDW 08:55 → ATL 11:45WN 4154	3h 34m Atlanta	ATL 15:19 → GRR 17:14DL 2058	7h 20m	100%	83%
Southwest + Frontiertwo ticketsDetails →	MDW 11:10 → DEN 12:40WN 2960	2h 28m Denver	DEN 15:08 → GRR 19:44F9 1248	7h 32m	92%	81%
Southwest + Americantwo ticketsDetails →	MDW 05:15 → LGA 08:15WN 2801	2h 20m New York	LGA 10:35 → GRR 12:52AA 4418 · flown by Republic	6h 36m	100%	78%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	55m Atlanta	ATL 09:50 → GRR 11:46DL 2547	4h 46m	90%	75%
Southwest + Deltatwo ticketsDetails →	MDW 17:05 → MSP 18:35WN 4643	3h 05m Minneapolis	MSP 21:40 → GRR 23:59DL 1711	5h 54m	95%	69%
Southwest + Deltatwo ticketsDetails →	MDW 07:55 → DTW 10:05WN 1775	2h 51m Detroit	DTW 12:56 → GRR 13:55DL 5390 · flown by Endeavor	5h 00m	100%	69%
Delta Details →	MDW 17:10 → ATL 20:22DL 1728	1h 37m Atlanta	ATL 21:59 → GRR 23:54DL 2865	5h 45m	87%	69%
Tight connection: often missed
Delta Details →	MDW 19:06 → MSP 20:51DL 4713 · flown by Endeavor	49m Minneapolis	MSP 21:40 → GRR 23:59DL 1711	3h 53m	52%	40%

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

MSP · 1h 20m · leaves 09:54 7%

ATL · 55m · leaves 06:00 10%

Afternoon and evening

MSP · 49m · leaves 19:06 48%

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