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 4 in 5 on time.

Nonstops


Southwest	MDW	BWI	1h 50m	80%	2.7%	1,786	Flying now
Frontier	MDW	BWI	1h 56m	83%	1.4%	71	Not flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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


Southwest Details →	MDW 07:40 → PVD 10:55WN 784	2h 07m Providence	PVD 13:02 → BWI 14:28WN 1094	5h 47m	100%	94%
Southwest Details →	MDW 07:40 → BOS 10:55WN 4611	2h 25m Boston	BOS 13:20 → BWI 15:00WN 733	6h 20m	100%	91%
Southwest Details →	MDW 07:40 → RDU 10:35WN 852	2h 45m Raleigh/Durham	RDU 13:20 → BWI 14:35WN 297	5h 55m	100%	88%
Southwest Details →	MDW 05:00 → TPA 08:25WN 2906	2h 15m Tampa	TPA 10:40 → BWI 13:00WN 1016	7h 00m	100%	88%
Southwest Details →	MDW 07:40 → ORF 10:45WN 1661	1h 30m Norfolk	ORF 12:15 → BWI 13:20WN 3185	4h 40m	100%	85%
Southwest Details →	MDW 05:10 → MCO 08:40WN 2815	2h 15m Orlando	MCO 10:55 → BWI 13:10WN 193	7h 00m	100%	85%
Southwest Details →	MDW 10:15 → MKE 11:00WN 1702	1h 25m Milwaukee	MKE 12:25 → BWI 15:20WN 2937	4h 05m	98%	83%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 15m Atlanta	ATL 11:10 → BWI 13:03DL 2711	6h 03m	95%	81%
Tight connection: often missed
Frontier Details →	MDW 12:11 → ATL 15:13F9 2144	53m Atlanta	ATL 16:06 → BWI 18:09F9 1080	4h 57m	63%	42%
Southwest Details →	MDW 18:00 → STL 19:10WN 2904	50m St Louis	STL 20:00 → BWI 23:05WN 3897	4h 00m	57%	23%
Southwest Details →	MDW 16:15 → DEN 18:00WN 2769	1h 05m Denver	DEN 19:05 → BWI 00:35 +1WN 1500	7h 18m	64%	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

AUS · 1h 05m · leaves 05:20 0%

HOU · 1h 15m · leaves 06:40 10%

MCO · 50m · leaves 06:30 24%

Afternoon and evening

ATL · 53m · leaves 12:11 37%

MSP · 1h 00m · leaves 15:30 40%

STL · 50m · leaves 18:00 43%

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.


Southwest WN 3054 MDW 07:15 → ATL Delta DL 2799 ATL 14:02 → BWI Connection details →	3h 57m	7h 38m	100%	79%
Southwest WN 1775 MDW 07:55 → DTW Frontier F9 1516 DTW 12:50 → BWI Connection details →	2h 45m	5h 31m	98%	76%
Southwest WN 1405 MDW 09:10 → BOS Delta DL 5644 BOS 15:50 → BWI Connection details →	3h 22m	7h 32m	100%	75%

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