Chicago (MDW) to Punta Cana (PUJ)

Lowest published fares for the months ahead: $405 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Sep 3–6, 2027; $250 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 1, 2026; 146 priced flights on 73 exact dates, 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.

Next: Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, Choose travelers and dates using their own trip details.

Chicago (MDW) to Punta Cana (PUJ): November 2026

Chicago (MDW) to Punta Cana (PUJ): December 2026

Chicago (MDW) to Punta Cana (PUJ): January 2027

Chicago (MDW) to Punta Cana (PUJ): February 2027

Chicago (MDW) to Punta Cana (PUJ): March 2027

Chicago (MDW) to Punta Cana (PUJ): April 2027

Chicago (MDW) to Punta Cana (PUJ): May 2027

Chicago (MDW) to Punta Cana (PUJ): June 2027

Chicago (MDW) to Punta Cana (PUJ): July 2027

Chicago (MDW) to Punta Cana (PUJ): August 2027

Chicago (MDW) to Punta Cana (PUJ): September 2027

Chicago (MDW) to Punta Cana (PUJ): October 2027

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 (Nov 20–23, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $73 a night, $219 for 3 nights · 4★ whala!urban punta cana, $71 a night, $213 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $338 a night, $1,013 for 3 nights
• Hotels in Punta Cana for these nights (Nov 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $67 a night, $467 for 7 nights · 4★ whala!urban punta cana, $71 a night, $497 for 7 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $309 a night, $2,160 for 7 nights
• Hotels in Punta Cana for these nights (Nov 24–29, 2026 · 5 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $66 a night, $328 for 5 nights · 4★ whala!urban punta cana, $71 a night, $355 for 5 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $288 a night, $1,441 for 5 nights
• Hotels in Punta Cana for these nights (Nov 26–29, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $68 a night, $204 for 3 nights · 4★ whala!urban punta cana, $71 a night, $213 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $300 a night, $899 for 3 nights
• Hotels in Punta Cana for these nights (Nov 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $70 a night, $210 for 3 nights · 4★ whala!urban punta cana, $71 a night, $213 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $299 a night, $896 for 3 nights
• Hotels in Punta Cana for these nights (Nov 28 – Dec 5, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $73 a night, $513 for 7 nights · 4★ whala!urban punta cana, $71 a night, $498 for 7 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $281 a night, $1,968 for 7 nights
• Hotels in Punta Cana for these nights (Dec 3–6, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $76 a night, $227 for 3 nights · 4★ whala!urban punta cana, $74 a night, $221 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $306 a night, $917 for 3 nights
• Hotels in Punta Cana for these nights (Dec 4–7, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $76 a night, $227 for 3 nights · 4★ whala!urban punta cana, $74 a night, $221 for 3 nights · 5★ TRS Turquesa Hotel - Adults Only - All Inclusive, $296 a night, $889 for 3 nights
• Hotels in Punta Cana for these nights (Dec 5–12, 2026 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $343 a night, $2,404 for 7 nights · 4★ whala!urban punta cana, $72 a night, $505 for 7 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $266 a night, $1,864 for 7 nights
• Hotels in Punta Cana for these nights (Dec 10–13, 2026 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $263 a night, $789 for 3 nights · 4★ whala!urban punta cana, $73 a night, $219 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $260 a night, $780 for 3 nights
• Hotels in Punta Cana for these nights (Dec 11–14, 2026 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $269 a night, $806 for 3 nights · 4★ whala!urban punta cana, $75 a night, $225 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $256 a night, $768 for 3 nights
• Hotels in Punta Cana for these nights (Dec 12–19, 2026 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $258 a night, $1,804 for 7 nights · 4★ whala!urban punta cana, $77 a night, $539 for 7 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $245 a night, $1,718 for 7 nights
• Hotels in Punta Cana for these nights (Dec 17–20, 2026 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $318 a night, $953 for 3 nights · 4★ whala!urban punta cana, $76 a night, $229 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $258 a night, $774 for 3 nights
• Hotels in Punta Cana for these nights (Dec 18–21, 2026 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $313 a night, $939 for 3 nights · 4★ whala!urban punta cana, $76 a night, $227 for 3 nights · 5★ TRS Turquesa Hotel - Adults Only - All Inclusive, $266 a night, $797 for 3 nights
• Hotels in Punta Cana for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $447 a night, $3,129 for 7 nights · 4★ whala!urban punta cana, $76 a night, $535 for 7 nights · 5★ TRS Turquesa Hotel - Adults Only - All Inclusive, $317 a night, $2,221 for 7 nights
• Hotels in Punta Cana for these nights (Dec 22–27, 2026 · 5 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $553 a night, $2,766 for 5 nights · 4★ whala!urban punta cana, $77 a night, $385 for 5 nights · 5★ TRS Turquesa Hotel - Adults Only - All Inclusive, $402 a night, $2,012 for 5 nights
• Hotels in Punta Cana for these nights (Dec 24–27, 2026 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $613 a night, $1,840 for 3 nights · 4★ whala!urban punta cana, $77 a night, $231 for 3 nights · 5★ TRS Turquesa Hotel - Adults Only - All Inclusive, $472 a night, $1,415 for 3 nights
• Hotels in Punta Cana for these nights (Dec 25–28, 2026 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge · 4★ whala!urban punta cana, $85 a night, $256 for 3 nights · 5★ TRS Turquesa Hotel - Adults Only - All Inclusive, $500 a night, $1,500 for 3 nights
• Hotels in Punta Cana for these nights (Dec 26 – Jan 2, 2027 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge · 4★ whala!urban punta cana, $98 a night, $689 for 7 nights · 5★ TRS Turquesa Hotel - Adults Only - All Inclusive, $860 a night, $6,019 for 7 nights
• Hotels in Punta Cana for these nights (Dec 30 – Jan 2, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge · 4★ whala!urban punta cana, $102 a night, $306 for 3 nights · 5★ TRS Turquesa Hotel - Adults Only - All Inclusive, $878 a night, $2,633 for 3 nights
• Hotels in Punta Cana for these nights (Dec 31 – Jan 3, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $659 a night, $1,978 for 3 nights · 4★ whala!urban punta cana, $101 a night, $303 for 3 nights · 5★ El Beso Adults Only At Ocean El Faro - All Inclusive, $775 a night, $2,325 for 3 nights
• Hotels in Punta Cana for these nights (Jan 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $508 a night, $1,524 for 3 nights · 4★ whala!urban punta cana, $98 a night, $295 for 3 nights · 5★ El Beso Adults Only At Ocean El Faro - All Inclusive, $567 a night, $1,700 for 3 nights
• Hotels in Punta Cana for these nights (Jan 2–9, 2027 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $420 a night, $2,938 for 7 nights · 4★ The MT Hotel, $92 a night, $641 for 7 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $384 a night, $2,685 for 7 nights
• Hotels in Punta Cana for these nights (Jan 7–10, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $375 a night, $1,125 for 3 nights · 4★ The MT Hotel, $84 a night, $252 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $403 a night, $1,210 for 3 nights
• Hotels in Punta Cana for these nights (Jan 8–11, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $375 a night, $1,125 for 3 nights · 4★ The MT Hotel, $86 a night, $258 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $405 a night, $1,215 for 3 nights
• Hotels in Punta Cana for these nights (Jan 9–16, 2027 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $382 a night, $2,674 for 7 nights · 4★ The MT Hotel, $84 a night, $590 for 7 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $340 a night, $2,382 for 7 nights
• Hotels in Punta Cana for these nights (Jan 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $393 a night, $1,180 for 3 nights · 4★ The MT Hotel, $84 a night, $253 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $356 a night, $1,067 for 3 nights
• Hotels in Punta Cana for these nights (Jan 15–18, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $393 a night, $1,180 for 3 nights · 4★ The MT Hotel, $90 a night, $269 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $329 a night, $986 for 3 nights
• Hotels in Punta Cana for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $397 a night, $2,777 for 7 nights · 4★ The MT Hotel, $84 a night, $589 for 7 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $328 a night, $2,293 for 7 nights
• Hotels in Punta Cana for these nights (Jan 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $400 a night, $1,201 for 3 nights · 4★ The MT Hotel, $84 a night, $252 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $384 a night, $1,152 for 3 nights
• Hotels in Punta Cana for these nights (Jan 22–25, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $399 a night, $1,198 for 3 nights · 4★ The MT Hotel, $86 a night, $258 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $394 a night, $1,181 for 3 nights
• Hotels in Punta Cana for these nights (Jan 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $388 a night, $2,715 for 7 nights · 4★ The MT Hotel, $82 a night, $577 for 7 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $331 a night, $2,316 for 7 nights
• Hotels in Punta Cana for these nights (Jan 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $387 a night, $1,161 for 3 nights · 4★ The MT Hotel, $84 a night, $252 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $292 a night, $877 for 3 nights
• Hotels in Punta Cana for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $380 a night, $1,140 for 3 nights · 4★ The MT Hotel, $86 a night, $258 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $286 a night, $858 for 3 nights
• Hotels in Punta Cana for these nights (Jan 30 – Feb 6, 2027 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $418 a night, $2,924 for 7 nights · 4★ The MT Hotel, $85 a night, $593 for 7 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $297 a night, $2,081 for 7 nights
• Hotels in Punta Cana for these nights (Feb 4–7, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $470 a night, $1,409 for 3 nights · 4★ The MT Hotel, $88 a night, $263 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $319 a night, $958 for 3 nights
• Hotels in Punta Cana for these nights (Feb 5–8, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $471 a night, $1,412 for 3 nights · 4★ The MT Hotel, $86 a night, $258 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $345 a night, $1,036 for 3 nights
• Hotels in Punta Cana for these nights (Feb 6–13, 2027 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $441 a night, $3,088 for 7 nights · 4★ The MT Hotel, $83 a night, $581 for 7 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $341 a night, $2,390 for 7 nights
• Hotels in Punta Cana for these nights (Feb 12–15, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $442 a night, $1,326 for 3 nights · 4★ The MT Hotel, $87 a night, $262 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $356 a night, $1,069 for 3 nights
• Hotels in Punta Cana for these nights (Feb 26 – Mar 1, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $397 a night, $1,191 for 3 nights · 4★ The MT Hotel, $86 a night, $258 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $288 a night, $864 for 3 nights
• Hotels in Punta Cana for these nights (Feb 27 – Mar 6, 2027 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $397 a night, $2,776 for 7 nights · 4★ The MT Hotel, $87 a night, $606 for 7 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $303 a night, $2,121 for 7 nights
• Hotels in Punta Cana for these nights (Mar 25–29, 2027 · 4 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge · 4★ The MT Hotel, $88 a night, $350 for 4 nights · 5★ TRS Turquesa Hotel - Adults Only - All Inclusive, $428 a night, $1,711 for 4 nights
• Hotels in Punta Cana for these nights (Mar 26–29, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge · 4★ The MT Hotel, $90 a night, $270 for 3 nights · 5★ TRS Turquesa Hotel - Adults Only - All Inclusive, $414 a night, $1,243 for 3 nights
• Hotels in Punta Cana for these nights (Mar 27 – Apr 3, 2027 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $449 a night, $3,140 for 7 nights · 4★ The MT Hotel, $84 a night, $585 for 7 nights · 5★ TRS Turquesa Hotel - Adults Only - All Inclusive, $480 a night, $3,361 for 7 nights
• Hotels in Punta Cana for these nights (Apr 23–26, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $430 a night, $1,291 for 3 nights · 4★ whala!urban punta cana, $85 a night, $254 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $274 a night, $822 for 3 nights
• Hotels in Punta Cana for these nights (Apr 24 – May 1, 2027 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge, $333 a night, $2,330 for 7 nights · 4★ The MT Hotel, $86 a night, $602 for 7 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $244 a night, $1,708 for 7 nights
• Hotels in Punta Cana for these nights (May 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $58 a night, $174 for 3 nights · 4★ whala!urban punta cana, $69 a night, $207 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $273 a night, $818 for 3 nights
• Hotels in Punta Cana for these nights (May 22–29, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $58 a night, $406 for 7 nights · 4★ whala!urban punta cana, $69 a night, $483 for 7 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $232 a night, $1,621 for 7 nights
• Hotels in Punta Cana for these nights (May 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $58 a night, $174 for 3 nights · 4★ whala!urban punta cana, $69 a night, $207 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $269 a night, $807 for 3 nights
• Hotels in Punta Cana for these nights (Jun 18–21, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $58 a night, $174 for 3 nights · 4★ whala!urban punta cana, $69 a night, $207 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $275 a night, $825 for 3 nights
• Hotels in Punta Cana for these nights (Jun 19–26, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $58 a night, $406 for 7 nights · 4★ whala!urban punta cana, $69 a night, $483 for 7 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $237 a night, $1,657 for 7 nights
• Hotels in Punta Cana for these nights (Jul 2–6, 2027 · 4 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $58 a night, $232 for 4 nights · 4★ The MT Hotel, $86 a night, $344 for 4 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $275 a night, $1,098 for 4 nights
• Hotels in Punta Cana for these nights (Jul 16–19, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $58 a night, $174 for 3 nights · 4★ The MT Hotel, $84 a night, $252 for 3 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $294 a night, $883 for 3 nights
• Hotels in Punta Cana for these nights (Jul 17–24, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Checkin El Cortecito, $58 a night, $406 for 7 nights · 4★ The MT Hotel, $85 a night, $596 for 7 nights · 5★ Melia Caribe Beach Resort - All Inclusive, $257 a night, $1,799 for 7 nights
• Hotels in Punta Cana for these nights (Aug 13–16, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge · 4★ The Westin® Puntacana Resort · 5★ Hyatt Zilara Cap Cana ‐ Adults Only ‐ All Inclusive
• Hotels in Punta Cana for these nights (Aug 14–21, 2027 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge · 4★ The Westin® Puntacana Resort · 5★ Hyatt Zilara Cap Cana ‐ Adults Only ‐ All Inclusive
• Hotels in Punta Cana for these nights (Sep 3–6, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge · 4★ The Westin® Puntacana Resort · 5★ Hyatt Zilara Cap Cana ‐ Adults Only ‐ All Inclusive
• Hotels in Punta Cana for these nights (Sep 10–13, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge · 4★ The Westin® Puntacana Resort · 5★ Hyatt Zilara Cap Cana ‐ Adults Only ‐ All Inclusive
• Hotels in Punta Cana for these nights (Sep 11–18, 2027 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge · 4★ The Westin® Puntacana Resort · 5★ Hyatt Zilara Cap Cana ‐ Adults Only ‐ All Inclusive
• Hotels in Punta Cana for these nights (Oct 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge · 4★ The Westin® Puntacana Resort · 5★ Hyatt Zilara Cap Cana ‐ Adults Only ‐ All Inclusive
• Hotels in Punta Cana for these nights (Oct 2–9, 2027 · 7 nights · 2 adults, 1 room): 3★ Punta Cana Villas Country and Ecolodge · 4★ The Westin® Puntacana Resort · 5★ Hyatt Zilara Cap Cana ‐ Adults Only ‐ All Inclusive

All hotels in Punta Cana

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

2026-11-20 → 2026-11-23 · Axel-exclusive $533

• Southwest Airlines WN2964 / WN782: MDW 2026-11-20 06:35:00 → PUJ 2026-11-20 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-11-20 06:35:00 → MCO 2026-11-20 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-11-20 12:10:00 → PUJ 2026-11-20 15:50:00.
• Southwest Airlines WN1999: PUJ 2026-11-23 16:10:00 → MDW 2026-11-23 19:15:00; nonstop; 305 minutes. Local airport times.

2026-11-20 → 2026-11-23 · Axel-exclusive $605

• Delta Air Lines DL1285 / DL1990: MDW 2026-11-20 06:00:00 → PUJ 2026-11-20 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-11-20 06:00:00 → ATL 2026-11-20 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-11-20 12:26:00 → PUJ 2026-11-20 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2026-11-23 15:53:00 → MDW 2026-11-23 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2026-11-23 15:53:00 → ATL 2026-11-23 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2026-11-23 21:20:00 → MDW 2026-11-23 22:17:00.

2026-11-24 · one way · Axel-exclusive $300

• Southwest Airlines WN2964 / WN782: MDW 2026-11-24 06:35:00 → PUJ 2026-11-24 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-11-24 06:35:00 → MCO 2026-11-24 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-11-24 12:10:00 → PUJ 2026-11-24 15:50:00.

2026-11-24 · one way · Axel-exclusive $354

• Delta Air Lines DL1285 / DL1990: MDW 2026-11-24 06:00:00 → PUJ 2026-11-24 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-11-24 06:00:00 → ATL 2026-11-24 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-11-24 12:26:00 → PUJ 2026-11-24 16:49:00.

2026-12-03 → 2026-12-06 · Axel-exclusive $465

• Southwest Airlines WN2964 / WN782: MDW 2026-12-03 06:35:00 → PUJ 2026-12-03 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-12-03 06:35:00 → MCO 2026-12-03 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-12-03 12:10:00 → PUJ 2026-12-03 15:50:00.
• Southwest Airlines WN822 / WN257: PUJ 2026-12-06 14:45:00 → MDW 2026-12-06 21:50:00; 1 stop(s) via BWI; 545 minutes. Local airport times.
  • WN822: PUJ 2026-12-06 14:45:00 → BWI 2026-12-06 17:40:00; layover at BWI: 185 minutes.
  • WN257: BWI 2026-12-06 20:45:00 → MDW 2026-12-06 21:50:00.

2026-12-03 → 2026-12-06 · Axel-exclusive $550

• Delta Air Lines DL1285 / DL1990: MDW 2026-12-03 06:00:00 → PUJ 2026-12-03 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-12-03 06:00:00 → ATL 2026-12-03 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-12-03 12:26:00 → PUJ 2026-12-03 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2026-12-06 15:53:00 → MDW 2026-12-06 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2026-12-06 15:53:00 → ATL 2026-12-06 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2026-12-06 21:20:00 → MDW 2026-12-06 22:17:00.

2026-12-17 → 2026-12-20 · Axel-exclusive $558

• Southwest Airlines WN2964 / WN782: MDW 2026-12-17 06:35:00 → PUJ 2026-12-17 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-12-17 06:35:00 → MCO 2026-12-17 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-12-17 12:10:00 → PUJ 2026-12-17 15:50:00.
• Southwest Airlines WN822 / WN257: PUJ 2026-12-20 14:45:00 → MDW 2026-12-20 21:50:00; 1 stop(s) via BWI; 545 minutes. Local airport times.
  • WN822: PUJ 2026-12-20 14:45:00 → BWI 2026-12-20 17:40:00; layover at BWI: 185 minutes.
  • WN257: BWI 2026-12-20 20:45:00 → MDW 2026-12-20 21:50:00.

2026-12-17 → 2026-12-20 · Axel-exclusive $660

• Delta Air Lines DL1285 / DL1990: MDW 2026-12-17 06:00:00 → PUJ 2026-12-17 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-12-17 06:00:00 → ATL 2026-12-17 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-12-17 12:26:00 → PUJ 2026-12-17 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2026-12-20 15:53:00 → MDW 2026-12-20 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2026-12-20 15:53:00 → ATL 2026-12-20 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2026-12-20 21:20:00 → MDW 2026-12-20 22:17:00.

2026-12-26 → 2027-01-02 · Axel-exclusive $676

• Southwest Airlines WN2964 / WN782: MDW 2026-12-26 06:35:00 → PUJ 2026-12-26 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2026-12-26 06:35:00 → MCO 2026-12-26 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2026-12-26 12:10:00 → PUJ 2026-12-26 15:50:00.
• Southwest Airlines WN1999: PUJ 2027-01-02 16:10:00 → MDW 2027-01-02 19:15:00; nonstop; 305 minutes. Local airport times.

2026-12-26 → 2027-01-02 · Axel-exclusive $770

• Delta Air Lines DL1285 / DL1990: MDW 2026-12-26 06:00:00 → PUJ 2026-12-26 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2026-12-26 06:00:00 → ATL 2026-12-26 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2026-12-26 12:26:00 → PUJ 2026-12-26 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-01-02 15:53:00 → MDW 2027-01-02 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-01-02 15:53:00 → ATL 2027-01-02 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-01-02 21:20:00 → MDW 2027-01-02 22:17:00.

2027-01-08 → 2027-01-11 · Axel-exclusive $483

• Southwest Airlines WN2964 / WN782: MDW 2027-01-08 06:35:00 → PUJ 2027-01-08 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2027-01-08 06:35:00 → MCO 2027-01-08 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2027-01-08 12:10:00 → PUJ 2027-01-08 15:50:00.
• Southwest Airlines WN1999: PUJ 2027-01-11 16:10:00 → MDW 2027-01-11 19:15:00; nonstop; 305 minutes. Local airport times.

2027-01-08 → 2027-01-11 · Axel-exclusive $550

• Delta Air Lines DL1285 / DL1990: MDW 2027-01-08 06:00:00 → PUJ 2027-01-08 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2027-01-08 06:00:00 → ATL 2027-01-08 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2027-01-08 12:26:00 → PUJ 2027-01-08 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-01-11 15:53:00 → MDW 2027-01-11 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-01-11 15:53:00 → ATL 2027-01-11 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-01-11 21:20:00 → MDW 2027-01-11 22:17:00.

2027-01-22 → 2027-01-25 · Axel-exclusive $483

• Southwest Airlines WN2964 / WN782: MDW 2027-01-22 06:35:00 → PUJ 2027-01-22 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2027-01-22 06:35:00 → MCO 2027-01-22 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2027-01-22 12:10:00 → PUJ 2027-01-22 15:50:00.
• Southwest Airlines WN1999: PUJ 2027-01-25 16:10:00 → MDW 2027-01-25 19:15:00; nonstop; 305 minutes. Local airport times.

2027-01-22 → 2027-01-25 · Axel-exclusive $550

• Delta Air Lines DL1285 / DL1990: MDW 2027-01-22 06:00:00 → PUJ 2027-01-22 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2027-01-22 06:00:00 → ATL 2027-01-22 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2027-01-22 12:26:00 → PUJ 2027-01-22 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-01-25 15:53:00 → MDW 2027-01-25 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-01-25 15:53:00 → ATL 2027-01-25 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-01-25 21:20:00 → MDW 2027-01-25 22:17:00.

2027-02-05 → 2027-02-08 · Axel-exclusive $483

• Southwest Airlines WN2964 / WN782: MDW 2027-02-05 06:35:00 → PUJ 2027-02-05 15:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2027-02-05 06:35:00 → MCO 2027-02-05 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2027-02-05 12:10:00 → PUJ 2027-02-05 15:50:00.
• Southwest Airlines WN1999: PUJ 2027-02-08 16:10:00 → MDW 2027-02-08 19:15:00; nonstop; 305 minutes. Local airport times.

2027-02-05 → 2027-02-08 · Axel-exclusive $550

• Delta Air Lines DL1285 / DL1990: MDW 2027-02-05 06:00:00 → PUJ 2027-02-05 16:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2027-02-05 06:00:00 → ATL 2027-02-05 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2027-02-05 12:26:00 → PUJ 2027-02-05 16:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-02-08 15:53:00 → MDW 2027-02-08 22:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-02-08 15:53:00 → ATL 2027-02-08 18:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-02-08 21:20:00 → MDW 2027-02-08 22:17:00.

2027-03-26 → 2027-03-29 · Axel-exclusive $609

• Southwest Airlines WN2964 / WN782: MDW 2027-03-26 06:35:00 → PUJ 2027-03-26 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2027-03-26 06:35:00 → MCO 2027-03-26 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2027-03-26 12:10:00 → PUJ 2027-03-26 14:50:00.
• Southwest Airlines WN1999: PUJ 2027-03-29 16:10:00 → MDW 2027-03-29 20:15:00; nonstop; 305 minutes. Local airport times.

2027-03-26 → 2027-03-29 · Axel-exclusive $694

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

2027-05-28 → 2027-05-31 · Axel-exclusive $468

• Southwest Airlines WN2964 / WN782: MDW 2027-05-28 06:35:00 → PUJ 2027-05-28 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2027-05-28 06:35:00 → MCO 2027-05-28 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2027-05-28 12:10:00 → PUJ 2027-05-28 14:50:00.
• Southwest Airlines WN1999: PUJ 2027-05-31 16:10:00 → MDW 2027-05-31 20:15:00; nonstop; 305 minutes. Local airport times.

2027-05-28 → 2027-05-31 · Axel-exclusive $530

• Delta Air Lines DL1285 / DL1990: MDW 2027-05-28 06:00:00 → PUJ 2027-05-28 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2027-05-28 06:00:00 → ATL 2027-05-28 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2027-05-28 12:26:00 → PUJ 2027-05-28 15:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-05-31 15:53:00 → MDW 2027-05-31 23:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-05-31 15:53:00 → ATL 2027-05-31 19:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-05-31 22:20:00 → MDW 2027-05-31 23:17:00.

2027-08-13 → 2027-08-16 · Axel-exclusive $428

• Southwest Airlines WN2964 / WN782: MDW 2027-08-13 06:35:00 → PUJ 2027-08-13 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2027-08-13 06:35:00 → MCO 2027-08-13 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2027-08-13 12:10:00 → PUJ 2027-08-13 14:50:00.
• Southwest Airlines WN1999: PUJ 2027-08-16 16:10:00 → MDW 2027-08-16 20:15:00; nonstop; 305 minutes. Local airport times.

2027-08-13 → 2027-08-16 · Axel-exclusive $485

• Delta Air Lines DL1285 / DL1990: MDW 2027-08-13 06:00:00 → PUJ 2027-08-13 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2027-08-13 06:00:00 → ATL 2027-08-13 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2027-08-13 12:26:00 → PUJ 2027-08-13 15:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-08-16 15:53:00 → MDW 2027-08-16 23:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-08-16 15:53:00 → ATL 2027-08-16 19:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-08-16 22:20:00 → MDW 2027-08-16 23:17:00.

2027-10-02 → 2027-10-09 · Axel-exclusive $428

• Southwest Airlines WN2964 / WN782: MDW 2027-10-02 06:35:00 → PUJ 2027-10-02 14:50:00; 1 stop(s) via MCO; 435 minutes. Local airport times.
  • WN2964: MDW 2027-10-02 06:35:00 → MCO 2027-10-02 10:20:00; layover at MCO: 110 minutes.
  • WN782: MCO 2027-10-02 12:10:00 → PUJ 2027-10-02 14:50:00.
• Southwest Airlines WN1999: PUJ 2027-10-09 16:10:00 → MDW 2027-10-09 20:15:00; nonstop; 305 minutes. Local airport times.

2027-10-02 → 2027-10-09 · Axel-exclusive $485

• Delta Air Lines DL1285 / DL1990: MDW 2027-10-02 06:00:00 → PUJ 2027-10-02 15:49:00; 1 stop(s) via ATL; 529 minutes. Local airport times.
  • DL1285: MDW 2027-10-02 06:00:00 → ATL 2027-10-02 09:03:00; layover at ATL: 203 minutes.
  • DL1990: ATL 2027-10-02 12:26:00 → PUJ 2027-10-02 15:49:00.
• Delta Air Lines DL1919 / DL1076: PUJ 2027-10-09 15:53:00 → MDW 2027-10-09 23:17:00; 1 stop(s) via ATL; 504 minutes. Local airport times.
  • DL1919: PUJ 2027-10-09 15:53:00 → ATL 2027-10-09 19:51:00; layover at ATL: 149 minutes.
  • DL1076: ATL 2027-10-09 22:20:00 → MDW 2027-10-09 23:17:00.

More dates for this route

• Nov 20, 2026 · Return options
• Nov 28, 2026 · Return options
• Dec 11, 2026 · Return options
• Dec 22, 2026 · Return options
• Dec 31, 2026 · Return options
• Jan 9, 2027 · Return options
• Jan 22, 2027 · Return options
• Feb 2, 2027 · Return options
• Feb 27, 2027 · Return options
• May 21, 2027 · Return options
• Jul 17, 2027 · Return options
• Oct 2, 2027 · Return options
• Hotels in Punta Cana with Axel

For AI assistants

• This page: Chicago (MDW) to Punta Cana (PUJ): 146 priced flights on 73 exact dates the months ahead, 1 adult in economy. In the dated tables a price link opens AI flight search for that row's exact dates and travelers; in the observed-flight lists the price is the customer link for the traveler, beside a “See flights for these dates” link for your own check. 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: Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, Choose travelers and dates using their own trip details.
• 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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