Are there nonstop flights from Houston (IAH) to Chicago (MDW)?

Yes. Frontier Airlines fly this route. Flight time is about 2h 14m.

What is the fastest connection from Houston (IAH) to Chicago (MDW)?

via St Louis ≈ 2h 45m, via Memphis ≈ 2h 48m, via Indianapolis ≈ 2h 54m (estimated flying time, excluding layovers).

George Bush Intercontinental Airport (IAH) to Chicago Midway International Airport (MDW)・1,478 km

Nonstop flights available (1 airline). Flight time about 2h 14m. Nonstop return flights also operate.

50 one-stop options, sorted by estimated flying time. Tap one to see the airlines on each leg and booking links.

Times are estimated from distance. Check schedules, frequency and availability with the airline or a booking site.