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 77% on time.

Nonstops


Southwest	BWI	MDW	2h 05m	77%	2.2%	1,767	Flying now
Frontier	BWI	MDW	2h 04m	77%	1.4%	71	Not 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 (Chicago is 1 h behind Baltimore). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	BWI 08:15 → CLT 09:55WN 148	1h 40m Charlotte	CLT 11:35 → MDW 12:35WN 4529	5h 20m	96%	92%
Southwest Details →	BWI 10:55 → ALB 12:15WN 155	3h 05m Albany	ALB 15:20 → MDW 16:35WN 164	6h 40m	100%	89%
Southwest Details →	BWI 06:20 → ATL 08:15WN 4689	1h 45m Atlanta	ATL 10:00 → MDW 11:00WN 224	5h 40m	100%	89%
Southwest Details →	BWI 06:25 → STL 07:45WN 1109	1h 10m St Louis	STL 08:55 → MDW 10:00WN 2570	4h 35m	98%	85%
Southwest Details →	BWI 14:40 → SDF 16:25WN 4885	3h 40m Louisville	SDF 20:05 → MDW 20:20WN 3329	6h 40m	100%	85%
Southwest Details →	BWI 06:25 → BNA 07:20WN 874	2h 00m Nashville	BNA 09:20 → MDW 11:00WN 1473	5h 35m	96%	84%
Delta Details →	BWI 07:00 → ATL 08:56DL 2579	2h 09m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 05m	99%	83%
Southwest Details →	BWI 06:15 → FLL 08:55WN 4627	1h 20m Fort Lauderdale	FLL 10:15 → MDW 12:15WN 1869	7h 00m	100%	80%
Tight connection: often missed
Southwest Details →	BWI 17:40 → MCO 20:15WN 172	1h 45m Orlando	MCO 22:00 → MDW 22:00WN 4762	7h 10m	72%	32%
Southwest Details →	BWI 17:05 → ROC 18:25WN 2693	1h 10m Rochester	ROC 19:35 → MDW 20:25WN 2693	4h 20m	66%	31%
Southwest Details →	BWI 18:00 → DTW 19:35WN 4159	50m Detroit	DTW 20:25 → MDW 20:35WN 1782	3h 35m	48%	18%

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

FLL · 1h 20m · leaves 06:15 0%

STL · 1h 10m · leaves 06:25 2%

DTW · 1h 10m · leaves 06:08 4%

Afternoon and evening

BOS · 1h 20m · leaves 13:50 19%

MCO · 50m · leaves 18:40 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.


American AA 2670 BWI 06:15 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	3h 42m	7h 20m	98%	94%
Southwest WN 4689 BWI 06:20 → ATL Delta DL 2417 ATL 11:05 → MDW Connection details →	2h 50m	6h 45m	100%	86%
Delta DL 2950 BWI 05:40 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	2h 29m	6h 20m	97%	84%

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