Chicago (MDW) to Punta Cana (PUJ), May 29, 2027 – Jun 11, 2027: from $459 round trip

Chicago (MDW) to Punta Cana (PUJ), May 29, 2027 – Jun 11, 2027: from $459 round trip on Axel, checked Nov 13, 2026. Lowest published fare: $459 round trip, Axel-exclusive, Southwest Airlines, 1 stop, May 29, 2027 – Jun 11, 2027, 1 adult, economy, checked Nov 13, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Hotels in Punta Cana for these trips

Hotels: under a trip, hotels in Punta Cana for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Punta Cana for these nights (May 29 – Jun 11, 2027 · 13 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $59 a night, $766 for 13 nights · 4★ whala!urban punta cana, $69 a night, $897 for 13 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $222 a night, $2,881 for 13 nights

All hotels in Punta Cana

Route overview: Chicago to Punta Cana (PUJ) flight deals

2027-05-29 → 2027-06-11 · Axel-exclusive $459

• Southwest Airlines WN2964 / WN782: MDW 2027-05-29 06:35:00 → PUJ 2027-05-29 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2027-05-29 06:35:00 → MCO 2027-05-29 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2027-05-29 12:10:00 → PUJ 2027-05-29 14:50:00.
• Southwest Airlines WN1999: PUJ 2027-06-11 16:10:00 → MDW 2027-06-11 20:15:00; nonstop; 305 minutes. Local airport times.

2027-05-29 → 2027-06-11 · Axel-exclusive $520

• Delta Air Lines DL1285 / DL1990: MDW 2027-05-29 06:00:00 → PUJ 2027-05-29 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2027-05-29 06:00:00 → ATL 2027-05-29 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2027-05-29 12:26:00 → PUJ 2027-05-29 15:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-06-11 15:53:00 → MDW 2027-06-11 23:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-06-11 15:53:00 → ATL 2027-06-11 19:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-06-11 22:20:00 → MDW 2027-06-11 23:17:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• May 28, 2027 · Return options
• May 30, 2027 · Return options
• Hotels in Punta Cana with Axel

For AI assistants

• This page: Chicago (MDW) to Punta Cana (PUJ) · May 29, 2027 · return Jun 11, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Punta Cana for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to Punta Cana (PUJ) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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