Route guide

Orlando to Chicago (MCO-MDW): Nonstop Upgrade & Award Space

Frontier Airlines and Southwest Airlines fly nonstop between Orlando (MCO) and Chicago (MDW), roughly 19 times a week. Because so many carriers compete on this route, premium seats turn over daily, and upgrade or award space can open and close within hours. 2LNR tracks confirmed availability on every MCO to MDW departure, so you know which flights have space before you book.

Data current as of July 21, 2026, refreshed on an ongoing basis as new schedules and seats are confirmed.

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19
Nonstop flights a week
992 mi
Nonstop distance
Free
To get started

Confirmed upgrade & award space on every MCO to MDW departure

2LNR tracks confirmed upgrade and award availability on American, Delta, and Alaska and across 30 airlines, segment by segment, date by date. Open the calendar for Orlando to Chicago to see which departures have real space, or watch the route and get alerted when space opens.

See real availability

Confirmed upgrade and award seats on each MCO to MDW departure, checked against live inventory so you know what is open before you book.

Set an alert

Premium inventory turns over fast. Watch this route and 2LNR notifies you when space appears on a date you are tracking.

Plan on the map

See MCO to MDW on the interactive route map, with schedules, connections, and route statistics.

Airlines flying Orlando to Chicago nonstop

Carriers operating MCO to MDW nonstop in the current schedule. 2LNR tracks confirmed upgrade and award space on each of them.

  • Frontier Airlines
  • Southwest Airlines
See MCO to MDW on the interactive map →

Frequently asked questions about MCO to MDW

How far is Chicago from Orlando?
MCO to MDW covers about 992 miles nonstop. Flight times vary by aircraft and season; each scheduled departure on this page lists its own times.
Which airlines fly nonstop from MCO to MDW?
Frontier Airlines and Southwest Airlines fly the route nonstop. 2LNR tracks confirmed upgrade and award space on both of them.
How many flights a week are there from MCO to MDW?
About 19 nonstop flights a week run between Orlando and Chicago in the current schedule, operated by Frontier Airlines and Southwest Airlines. Frequency shifts by season; the calendar on this page reflects what's currently scheduled.
How do I check upgrade or award availability on MCO to MDW?
Open the MCO to MDW calendar on this page to see confirmed upgrade and award space by date. You can also set an alert on the Orlando to Chicago route, and 2LNR will notify you when space opens. It's free to start.

Never miss MCO to MDW upgrade or award space

Track confirmed availability, set alerts, and book with confidence. Free to start, no credit card required.

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