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

No clear winner: Frontier’s MDW → EWR flights land within a few points of 2 in 3 on time whatever the hour.

Nonstops (none in the current schedule)


Frontier	MDW	EWR	2h 04m	66%	5.6%	71	Not flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

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


Southwest + Unitedtwo ticketsDetails →	MDW 05:00 → TPA 08:25WN 2906	2h 32m Tampa	TPA 10:57 → EWR 13:48UA 2858	7h 48m	100%	86%
Southwest + Unitedtwo ticketsDetails →	MDW 07:40 → RDU 10:35WN 852	2h 05m Raleigh/Durham	RDU 12:40 → EWR 14:32UA 3443 · flown by Republic	5h 52m	98%	85%
Southwest + Unitedtwo ticketsDetails →	MDW 05:20 → AUS 07:50WN 2726	2h 19m Austin	AUS 10:09 → EWR 15:00UA 1499	8h 40m	100%	84%
Southwest + Unitedtwo ticketsDetails →	MDW 07:50 → STL 09:10WN 2900	3h 13m St Louis	STL 12:23 → EWR 16:00UA 3573 · flown by Republic	7h 10m	100%	82%
Southwest + Unitedtwo ticketsDetails →	MDW 06:00 → DCA 08:45WN 4976	2h 15m Washington	DCA 11:00 → EWR 12:22UA 4508 · flown by GoJet	5h 22m	100%	80%
Southwest + Unitedtwo ticketsDetails →	MDW 05:10 → MCO 08:40WN 2815	1h 42m Orlando	MCO 10:22 → EWR 13:05UA 2120	6h 55m	90%	79%
Southwest + Unitedtwo ticketsDetails →	MDW 07:45 → SDF 10:05WN 1267	3h 02m Louisville	SDF 13:07 → EWR 15:30UA 3694 · flown by Republic	6h 45m	100%	78%
Southwest + Unitedtwo ticketsDetails →	MDW 07:50 → CLT 10:55WN 2749	3h 40m Charlotte	CLT 14:35 → EWR 16:40UA 3450 · flown by Republic	7h 50m	100%	76%

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 · 1h 08m · leaves 06:00 9%

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