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

No clear winner: airlines and hours on this route all land within a few points of 78% on time.

Nonstops


Southwest	MSP	MDW	1h 30m	80%	1.8%	1,593	Flying now
Delta	MSP	MDW	1h 40m	75%	1.3%	1,061	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. Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	MSP 05:50 → DEN 06:55WN 1525	3h 05m Denver	DEN 10:00 → MDW 13:25WN 755	7h 35m	100%	87%
Delta Details →	MSP 05:20 → ATL 08:48DL 1062	2h 17m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 45m	98%	84%
Delta Details →	MSP 06:04 → DTW 08:47DL 1461	3h 38m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	6h 42m	100%	81%
Southwest Details →	MSP 07:05 → BNA 09:10WN 1528	3h 45m Nashville	BNA 12:55 → MDW 14:30WN 1430	7h 25m	100%	78%
Delta Details →	MSP 08:28 → ATL 11:54DL 1052	3h 21m Atlanta	ATL 15:15 → MDW 16:15DL 1728	7h 47m	100%	75%
Southwest Details →	MSP 05:25 → BWI 08:50WN 3658	3h 40m Baltimore	BWI 12:30 → MDW 13:30WN 435	8h 05m	100%	69%
Delta Details →	MSP 16:09 → ATL 19:46DL 1028	1h 29m Atlanta	ATL 21:15 → MDW 22:17DL 1076	6h 08m	89%	67%
Southwest Details →	MSP 17:40 → STL 19:10WN 2974	2h 35m St Louis	STL 21:45 → MDW 22:55WN 3957	5h 10m	96%	64%

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 3831 MSP 08:50 → OMA Southwest WN 4470 OMA 13:10 → MDW Connection details →	2h 54m	5h 45m	97%	89%
United UA 2041 MSP 05:45 → DEN Southwest WN 755 DEN 10:00 → MDW Connection details →	3h 07m	7h 40m	98%	85%
American AA 894 MSP 06:19 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	1h 35m	6h 16m	86%	83%

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