Chicago to Chicago (MDW–ORD) — Airlines, Schedules & Connections

MDW Airport Page →
15 mi airlines charter/private 1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 95 1-stop flights Verified 3w ago
Also flown by charter / private operators.
Nonstop Charter / private 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

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.

✦ 1-Stop connections via 10 hubs
MKE Milwaukee 2h 46m WN → AAACAS Milwaukee (MKE) to Chicago flights
GRR Grand Rapids 2h 55m WN → AAASBA Grand Rapids (GRR) to Chicago flights
IND Indianapolis 3h 23m JLGWN → AAACAS Indianapolis (IND) to Chicago flights
STL St Louis 3h 26m JRENSHWN → AAACAS St Louis (STL) to Chicago flights
DTW Detroit 3h 33m AFDLKE → AAACAM Detroit (DTW) to Chicago flights
CVG Cincinnati / Covington 3h 37m WN → AAACAS Cincinnati / Covington (CVG) to Chicago flights
CLE Cleveland 3h 38m UAWN → AAASAV Cleveland (CLE) to Chicago flights
SDF Louisville 3h 40m WN → AAACAS Louisville (SDF) to Chicago flights
CMH Columbus 3h 43m EJAWN → AAASAY Columbus (CMH) to Chicago flights
MSP Minneapolis 3h 59m DLKEVS → AAACAF Minneapolis (MSP) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Chicago to Chicago
Connecting service available through multiple hubs.
2 Airlines 15 mi

MDW–ORD had nonstop service from United Airlines and Southwest Airlines, last on the schedule in May 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.

Also explore MDW Routes ORD Routes MDW Live Flights ORD Live Flights MDW Delays ORD Delays
All flights from Chicago (ORD) Chicago to Chicago flights
Carriers on this route

Airline Landscape

Carriers that operated nonstop MDW–ORD service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
UA United Airlines 0 – – 28% Star Alliance –
WN Southwest Airlines 0 – – 28% – –
Alliance coverage
Star Alliance: UA (0 flights/wk, 0%)
Unaffiliated: WN (0 flights/wk, 0%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.
Connections

Connection Landscape

1-stop and 2-stop options for MDW to ORD.
1-STOP
One-Stop Connections
95
Hubs
~2h
Fastest
~25h
Longest
MKE ~2h 46m GRR ~2h 55m IND ~3h 23m STL ~3h 26m DTW ~3h 33m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
4,852
Candidates
Two-stop connections loaded in the connections tab above.
Connections computed from published schedules with minimum connection time verification. Use the interactive explorer above the fold to filter by airline, tier, and layover time.
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
MDW → ORD
28%
Frequent delays expected. Consider flexible booking.
Departing
28%
Arriving
83%
Return
ORD → MDW
10%
Frequent delays expected. Consider flexible booking.
Departing
10%
Arriving
85%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays → ORD delays →
Alternatives

Other ways to reach Chicago from Chicago

Nearby airports with service to Chicago O'Hare International Airport.
Metric MDW→ORD SBN→ORD RFD→ORD
Distance from MDW – 74 mi 75 mi
Nonstop airlines – 7 4
Weekly flights – 142 30
Departure OTP 28% – –
South Bend (SBN) to Chicago flights · Chicago/Rockford (RFD) to Chicago flights · Milwaukee (MKE) to Chicago flights
Airports within 200 miles of MDW with service to Chicago O'Hare International Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
0h
Chicago is 0 hours the same as Chicago.
MDW: CDT · ORD: CDT

When it's 6:00 PM in Chicago, it's 6:00 PM in Chicago.
Distance & Flight Time
15 mi / 25 km
Getting from ORD

CTA Blue Line runs 24/7 from O'Hare to downtown Chicago (45 min, $5). Taxis use a flat-rate zone system; downtown is around $40–45 plus tip. Ride-shares are typically $30–50.The Airport Transit System (ATS) connects all terminals and parking. Metra commuter rail does not serve O'Hare directly; transfer downtown via Blue Line.

Chicago Climate

Continental climate with four distinct seasons. Summers are warm and humid (25–32°C) with afternoon thunderstorms. Winters are cold (−10 to −2°C) with heavy snowfall that regularly delays flights December through March.

Spring and fall are mild but unpredictable. Pack layers. Lake Michigan moderates temperatures near the lakefront, but O'Hare sits inland and runs colder.

Check current weather forecasts before travel.
Facts

MDW–ORD Quick Facts

Key statistics for the Chicago to Chicago route.
Route details
Distance15 mi / 25 km
Time difference0 hours
Airlines (nonstop)2
1-stop connectionsAvailable
Origin: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
Destination: ORD
Full nameChicago O'Hare International Airport
IATA / ICAOORD / KORD
TimezoneAmerica/Chicago
Passengers/yr80.0M
Elevation680 ft / 207 m
FAQ

Frequently Asked Questions

Common questions about MDW to ORD flights.
2 airlines operated the nonstop from MDW to ORD: United Airlines and Southwest Airlines. The last scheduled nonstop was in May 2026. There's no nonstop right now, so today you'd fly it with one stop. See the connection options above, ranked by layover.
Not right now. The last scheduled nonstop was in May 2026. You can still fly it with one stop, and the connecting options above are sorted by layover.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include General Mitchell, Gerald R. Ford and Indianapolis.
Yes, return flights from ORD to MDW are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include SBN, RFD and MKE. See the Alternatives section for a full comparison.
Click the 'Search Flights' button to check availability and prices on Google Flights. You can also compare airlines and schedules on this page to find the best option.
See the On-Time Performance section for the latest delay data at both airports. This shows departure and arrival reliability to help you plan.
Route data is updated regularly from official airline schedules. On-time performance data comes from recent airport delay snapshots.

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 South Bend (SBN), Chicago/Rockford (RFD) and Milwaukee (MKE).