SFO and MDW are approximately 1,850 miles apart by great-circle distance.
Yes. Roame's current schedule feed shows nonstop service from SFO to MDW.
Airlines represented in the current schedule are Southwest Airlines (WN).
Aircraft listed in the current schedule include Boeing 737-800 Winglets (73H), Boeing 737 MAX 8 (7M8), 7S7 and JET.