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

The nonstop is quickest: Southwest MDW → BZN (3h 10m), on time 7 times in 10. Delta via Minneapolis (5h 56m) is more reliable, 87%, but takes 2h 46m longer.

Nonstops (seasonal or thin)


Southwest	MDW	BZN	3h 10m	71%	0.0%	120	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

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


Delta Details →	MDW 09:54 → MSP 11:35DL 5469 · flown by Endeavor	1h 42m Minneapolis	MSP 13:17 → BZN 14:48DL 2946	5h 56m	98%	87%
Southwest + Unitedtwo ticketsDetails →	MDW 06:50 → DEN 08:20WN 2765	3h 12m Denver	DEN 11:32 → BZN 13:20UA 1248	7h 30m	100%	86%
Southwest Details →	MDW 05:15 → DEN 06:50WN 2989	1h 00m Denver	DEN 07:50 → BZN 09:35WN 826	5h 20m	98%	81%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 14m Atlanta	ATL 11:09 → BZN 13:11DL 406	8h 13m	95%	75%
Southwest + Unitedtwo ticketsDetails →	MDW 14:30 → DEN 16:10WN 2768	3h 15m Denver	DEN 19:25 → BZN 21:14UA 1347	7h 44m	92%	74%
Southwest + Unitedtwo ticketsDetails →	MDW 09:55 → DEN 11:30WN 2654	2h 14m Denver	DEN 13:44 → BZN 15:33UA 513	6h 38m	90%	74%
Southwest + Unitedtwo ticketsDetails →	MDW 11:10 → DEN 12:40WN 2960	2h 35m Denver	DEN 15:15 → BZN 17:10UA 6030 · flown by SkyWest	7h 00m	92%	68%
Southwest + Deltatwo ticketsDetails →	MDW 17:05 → MSP 18:35WN 4643	3h 48m Minneapolis	MSP 22:23 → BZN 23:52DL 2954	7h 53m	98%	67%
Tight connection: often missed
Delta Details →	MDW 19:06 → MSP 20:51DL 4713 · flown by Endeavor	1h 32m Minneapolis	MSP 22:23 → BZN 23:52DL 2954	5h 52m	72%	52%
Southwest Details →	MDW 18:00 → DEN 19:45WN 1497	1h 25m Denver	DEN 21:10 → BZN 22:58WN 1505	5h 55m	72%	32%
Southwest Details →	MDW 09:55 → DEN 11:30WN 2654	1h 00m Denver	DEN 12:30 → BZN 14:10WN 4219	5h 15m	68%	31%

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

DEN · 1h 00m · leaves 05:15 2%

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