Route guide

Chicago to Milwaukee (MDW-MKE): Nonstop Upgrade & Award Space

Southwest Airlines flies nonstop from Chicago (MDW) to Milwaukee (MKE) just three times a week. With so few departures, each one carries the only premium seats on the route that day. 2LNR tracks confirmed upgrade and award space on all of them, so a rare opening doesn't slip past you.

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

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3
Nonstop flights a week
81 mi
Nonstop distance
Free
To get started

Confirmed upgrade & award space on every MDW to MKE 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 Chicago to Milwaukee 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 MDW to MKE 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 MDW to MKE on the interactive route map, with schedules, connections, and route statistics.

Airlines flying Chicago to Milwaukee nonstop

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

  • Southwest Airlines
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Frequently asked questions about MDW to MKE

How far is Milwaukee from Chicago?
MDW to MKE covers about 81 miles nonstop. Flight times vary by aircraft and season; each scheduled departure on this page lists its own times.
Which airlines fly nonstop from MDW to MKE?
Southwest Airlines is currently the only airline flying MDW to MKE nonstop. 2LNR tracks confirmed upgrade and award space on every Southwest Airlines departure.
How often does MDW to MKE operate?
The nonstop currently runs three times a week, on Southwest Airlines. Thin schedules like this change by season, and an alert will catch anything added.
How do I check upgrade or award availability on MDW to MKE?
Open the MDW to MKE calendar on this page to see confirmed upgrade and award space by date. You can also set an alert on the Chicago to Milwaukee route, and 2LNR will notify you when space opens. It's free to start.

Never miss MDW to MKE upgrade or award space

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

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