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 EWR → MDW flights land within a few points of 2 in 3 on time whatever the hour.

Nonstops (none in the current schedule)


Frontier	EWR	MDW	2h 30m	67%	5.6%	71	Not flying now

Best connections, any airlines

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 Newark). Layovers up to 4 hours. Pick a connection for the details.


American + Southwesttwo ticketsDetails →	EWR 06:00 → CLT 08:01AA 2505	3h 34m Charlotte	CLT 11:35 → MDW 12:35WN 4529	7h 35m	97%	91%
United + Deltatwo ticketsDetails →	EWR 06:00 → ATL 08:23UA 1012	2h 42m Atlanta	ATL 11:05 → MDW 12:05DL 2417	7h 05m	100%	84%
United + Deltatwo ticketsDetails →	EWR 07:30 → DTW 09:31UA 3672 · flown by Republic	2h 54m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	6h 16m	100%	81%
United + Southwesttwo ticketsDetails →	EWR 11:54 → IND 14:07UA 3446 · flown by Republic	3h 33m Indianapolis	IND 17:40 → MDW 17:55WN 961	7h 01m	97%	78%
United + Southwesttwo ticketsDetails →	EWR 08:30 → CLE 10:08UA 1833	1h 57m Cleveland	CLE 12:05 → MDW 12:20WN 1161	4h 50m	94%	78%
Delta + Southwesttwo ticketsDetails →	EWR 07:05 → ATL 09:22DL 1673	3h 08m Atlanta	ATL 12:30 → MDW 13:25WN 225	7h 20m	97%	71%
Delta + Southwesttwo ticketsDetails →	EWR 06:15 → MSP 08:13DL 1641	2h 12m Minneapolis	MSP 10:25 → MDW 11:55WN 4345	6h 40m	92%	71%
United + Southwesttwo ticketsDetails →	EWR 09:00 → GRR 11:12UA 3486 · flown by Republic	1h 33m Grand Rapids	GRR 12:45 → MDW 12:50WN 1895	4h 50m	82%	69%

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

DTW · 55m · 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