Route guide

Chicago to Punta Cana (MDW-PUJ): Nonstop Upgrade & Award Space

Southwest Airlines flies nonstop from Chicago (MDW) to Punta Cana (PUJ) 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.

See MDW to PUJ on the interactive map Get started free
3
Nonstop flights a week
1,968 mi
Nonstop distance
Free
To get started

Confirmed upgrade & award space on every MDW to PUJ 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 Punta Cana 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 PUJ 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 PUJ on the interactive route map, with schedules, connections, and route statistics.

Airlines flying Chicago to Punta Cana nonstop

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

  • Southwest Airlines
See MDW to PUJ on the interactive map →

Frequently asked questions about MDW to PUJ

How far is Punta Cana from Chicago?
MDW to PUJ covers about 1,968 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 PUJ?
Southwest Airlines is currently the only airline flying MDW to PUJ nonstop. 2LNR tracks confirmed upgrade and award space on every Southwest Airlines departure.
How often does MDW to PUJ 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 PUJ?
Open the MDW to PUJ calendar on this page to see confirmed upgrade and award space by date. You can also set an alert on the Chicago to Punta Cana route, and 2LNR will notify you when space opens. It's free to start.

Never miss MDW to PUJ upgrade or award space

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

Get started free