Chicago to Chicago (ORD–MDW) — Airlines, Schedules & Connections
No flights match your filters.
No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.
Most recently operated nonstop flights — the month shown is when each was last scheduled. Most destinations remain reachable with a connection.
No discontinued nonstop flights on record for this route.
ORD–MDW had nonstop service from Southwest Airlines and United Airlines, last on the schedule in June 2026. There's no nonstop on it right now, so today you'd fly it with one stop. The connecting options below are sorted by layover.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 1 | – | – | – | – | |
| UA United Airlines | 0 | – | – | Star Alliance | – |
Connection Landscape
On-Time Performance
Other ways to reach Chicago from Chicago
| Metric | ORD→MDW | GYY→MDW | RFD→MDW |
|---|---|---|---|
| Distance from ORD | – | 36 mi | 63 mi |
| Nonstop airlines | – | 1 | 1 |
| Weekly flights | – | 1 | 1 |
| Departure OTP | 21% | – | – |
Travel Essentials
ORD: CDT · MDW: CDT
When it's 6:00 PM in Chicago, it's 6:00 PM in Chicago.
CTA Blue Line runs 24/7 from downtown Loop stations to O'Hare (45 min, $5). Pace buses serve suburbs. Ride-shares cost $35–55 from downtown depending on traffic; add 30+ minutes during rush hour on the Kennedy Expressway.Economy parking lots E/F connect via ATS people mover. Terminal 5 (international) is separate from Terminals 1–3; allow extra time for inter-terminal transfers.
ORD–MDW Quick Facts
Frequently Asked Questions
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via General Mitchell, Gerald R. Ford and Indianapolis. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Gary (GYY), Chicago/Rockford (RFD) and Milwaukee (MKE).