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

Connect in the morning. The same one-hour layover misses 7% of the time at 10 am and 22% of the time at 8 pm.

Nonstops (seasonal or thin)


Southwest	SAT	MDW	2h 35m	78%	1.1%	661	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. Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	SAT 05:45 → DEN 07:00WN 3565	3h 00m Denver	DEN 10:00 → MDW 13:25WN 755	7h 40m	100%	87%
American + Southwesttwo ticketsDetails →	SAT 06:01 → CLT 10:00AA 1119	1h 35m Charlotte	CLT 11:35 → MDW 12:35WN 4529	6h 34m	87%	83%
Delta Details →	SAT 05:25 → ATL 08:53DL 1073	2h 12m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 40m	97%	82%
Southwest Details →	SAT 05:25 → HOU 06:32WN 1315	1h 38m Houston	HOU 08:10 → MDW 10:40WN 1294	5h 15m	96%	81%
Southwest Details →	SAT 06:05 → ELP 06:35WN 4582	1h 05m El Paso	ELP 07:40 → MDW 11:35WN 1813	5h 30m	98%	80%
Delta Details →	SAT 05:15 → DTW 09:22DL 2497	3h 03m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	7h 31m	99%	79%
Southwest Details →	SAT 07:15 → DAL 08:25WN 1356	1h 40m Dallas	DAL 10:05 → MDW 12:20WN 1357	5h 05m	97%	78%
Southwest Details →	SAT 06:55 → BNA 09:10WN 3557	3h 45m Nashville	BNA 12:55 → MDW 14:30WN 1430	7h 35m	100%	78%
Tight connection: often missed
Southwest Details →	SAT 18:30 → HOU 19:35WN 3573	1h 10m Houston	HOU 20:45 → MDW 23:10WN 2044	4h 40m	64%	24%
Southwest Details →	SAT 20:05 → DAL 21:15WN 1338	1h 07m Dallas	DAL 22:22 → MDW 01:00 +1WN 1359	4h 32m	57%	18%
Southwest Details →	SAT 16:55 → BNA 19:10WN 4193	1h 15m Nashville	BNA 20:25 → MDW 21:55WN 4286	5h 00m	57%	17%

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

ELP · 1h 05m · leaves 06:05 2%

ATL · 59m · leaves 06:40 7%

LAS · 55m · leaves 10:55 38%

Afternoon and evening

BNA · 1h 15m · leaves 16:55 43%

DAL · 1h 07m · leaves 20:05 43%

DEN · 50m · leaves 18:30 57%

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