Chicago (MDW) to Puerto Vallarta (PVR)

Lowest published fares for the months ahead: $399 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Sep 3–6, 2027; $250 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 1, 2026; 144 priced flights on 72 exact dates, 1 adult, economy, checked Nov 14, 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 Puerto Vallarta (PVR): November 2026

Travel dates Airline Stops Total price
Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $558
Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $612
Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $558
Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $612
Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $512
Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $561
Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $512
Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $561

Chicago (MDW) to Puerto Vallarta (PVR): December 2026

Travel dates Airline Stops Total price
Dec 1, 2026 · One way · Compare return dates departing Dec 1, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $250
Dec 1, 2026 · One way · Compare return dates departing Dec 1, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $275
Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $250
Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $275
Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $558
Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $612
Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $250
Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $275
Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $558
Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $612
Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $558
Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $612
Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $651
Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $714
Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $350
Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $385
Dec 22, 2026 – Dec 27, 2026 · 5 nights · Compare return dates departing Dec 22, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $651
Dec 22, 2026 – Dec 27, 2026 · 5 nights · Compare return dates departing Dec 22, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $714
Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $651
Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $714
Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $651
Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $714
Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $651
Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $714
Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $350
Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $385
Dec 30, 2026 – Jan 2, 2027 · 3 nights · Compare return dates departing Dec 30, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $651
Dec 30, 2026 – Jan 2, 2027 · 3 nights · Compare return dates departing Dec 30, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $714
Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026 Southwest Airlines Up to 1 stop each way Axel-exclusive $651
Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026 Delta Air Lines Up to 1 stop each way Axel-exclusive $714

Chicago (MDW) to Puerto Vallarta (PVR): January 2027

Travel dates Airline Stops Total price
Jan 1, 2027 – Jan 4, 2027 · 3 nights · Compare return dates departing Jan 1, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $558
Jan 1, 2027 – Jan 4, 2027 · 3 nights · Compare return dates departing Jan 1, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $612
Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $558
Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $612
Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $250
Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $275
Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $250
Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $275
Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $250
Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $275
Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $250
Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $275
Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $510

Chicago (MDW) to Puerto Vallarta (PVR): February 2027

Travel dates Airline Stops Total price
Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $250
Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $275
Feb 4, 2027 – Feb 7, 2027 · 3 nights · Compare return dates departing Feb 4, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Feb 4, 2027 – Feb 7, 2027 · 3 nights · Compare return dates departing Feb 4, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Feb 5, 2027 – Feb 8, 2027 · 3 nights · Compare return dates departing Feb 5, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $465
Feb 5, 2027 – Feb 8, 2027 · 3 nights · Compare return dates departing Feb 5, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $510
Feb 6, 2027 – Feb 13, 2027 · 7 nights · Compare return dates departing Feb 6, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $500
Feb 6, 2027 – Feb 13, 2027 · 7 nights · Compare return dates departing Feb 6, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $548
Feb 9, 2027 · One way · Compare return dates departing Feb 9, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $250
Feb 9, 2027 · One way · Compare return dates departing Feb 9, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $275
Feb 11, 2027 – Feb 14, 2027 · 3 nights · Compare return dates departing Feb 11, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $500
Feb 11, 2027 – Feb 14, 2027 · 3 nights · Compare return dates departing Feb 11, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $548
Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $535
Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $587
Feb 13, 2027 – Feb 20, 2027 · 7 nights · Compare return dates departing Feb 13, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $500
Feb 13, 2027 – Feb 20, 2027 · 7 nights · Compare return dates departing Feb 13, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $548
Feb 26, 2027 – Mar 1, 2027 · 3 nights · Compare return dates departing Feb 26, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $477
Feb 26, 2027 – Mar 1, 2027 · 3 nights · Compare return dates departing Feb 26, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $523
Feb 27, 2027 – Mar 6, 2027 · 7 nights · Compare return dates departing Feb 27, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $477
Feb 27, 2027 – Mar 6, 2027 · 7 nights · Compare return dates departing Feb 27, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $523

Chicago (MDW) to Puerto Vallarta (PVR): March 2027

Travel dates Airline Stops Total price
Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $513
Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $560
Mar 26, 2027 – Mar 29, 2027 · 3 nights · Compare return dates departing Mar 26, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $513
Mar 26, 2027 – Mar 29, 2027 · 3 nights · Compare return dates departing Mar 26, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $560
Mar 27, 2027 – Apr 3, 2027 · 7 nights · Compare return dates departing Mar 27, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $503
Mar 27, 2027 – Apr 3, 2027 · 7 nights · Compare return dates departing Mar 27, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $549

Chicago (MDW) to Puerto Vallarta (PVR): April 2027

Travel dates Airline Stops Total price
Apr 23, 2027 – Apr 26, 2027 · 3 nights · Compare return dates departing Apr 23, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $420
Apr 23, 2027 – Apr 26, 2027 · 3 nights · Compare return dates departing Apr 23, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $455
Apr 24, 2027 – May 1, 2027 · 7 nights · Compare return dates departing Apr 24, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $420
Apr 24, 2027 – May 1, 2027 · 7 nights · Compare return dates departing Apr 24, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $455

Chicago (MDW) to Puerto Vallarta (PVR): May 2027

Travel dates Airline Stops Total price
May 21, 2027 – May 24, 2027 · 3 nights · Compare return dates departing May 21, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $420
May 21, 2027 – May 24, 2027 · 3 nights · Compare return dates departing May 21, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $455
May 22, 2027 – May 29, 2027 · 7 nights · Compare return dates departing May 22, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $441
May 22, 2027 – May 29, 2027 · 7 nights · Compare return dates departing May 22, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $478
May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $462
May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $501

Chicago (MDW) to Puerto Vallarta (PVR): June 2027

Travel dates Airline Stops Total price
Jun 18, 2027 – Jun 21, 2027 · 3 nights · Compare return dates departing Jun 18, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $420
Jun 18, 2027 – Jun 21, 2027 · 3 nights · Compare return dates departing Jun 18, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $455
Jun 19, 2027 – Jun 26, 2027 · 7 nights · Compare return dates departing Jun 19, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $420
Jun 19, 2027 – Jun 26, 2027 · 7 nights · Compare return dates departing Jun 19, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $455

Chicago (MDW) to Puerto Vallarta (PVR): July 2027

Travel dates Airline Stops Total price
Jul 2, 2027 – Jul 6, 2027 · 4 nights · Compare return dates departing Jul 2, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $441
Jul 2, 2027 – Jul 6, 2027 · 4 nights · Compare return dates departing Jul 2, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $478
Jul 16, 2027 – Jul 19, 2027 · 3 nights · Compare return dates departing Jul 16, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $420
Jul 16, 2027 – Jul 19, 2027 · 3 nights · Compare return dates departing Jul 16, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $455
Jul 17, 2027 – Jul 24, 2027 · 7 nights · Compare return dates departing Jul 17, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $420
Jul 17, 2027 – Jul 24, 2027 · 7 nights · Compare return dates departing Jul 17, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $455

Chicago (MDW) to Puerto Vallarta (PVR): August 2027

Travel dates Airline Stops Total price
Aug 13, 2027 – Aug 16, 2027 · 3 nights · Compare return dates departing Aug 13, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $420
Aug 13, 2027 – Aug 16, 2027 · 3 nights · Compare return dates departing Aug 13, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $455
Aug 14, 2027 – Aug 21, 2027 · 7 nights · Compare return dates departing Aug 14, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $420
Aug 14, 2027 – Aug 21, 2027 · 7 nights · Compare return dates departing Aug 14, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $455

Chicago (MDW) to Puerto Vallarta (PVR): September 2027

Travel dates Airline Stops Total price
Sep 3, 2027 – Sep 6, 2027 · 3 nights · Compare return dates departing Sep 3, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $399
Sep 3, 2027 – Sep 6, 2027 · 3 nights · Compare return dates departing Sep 3, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $432
Sep 10, 2027 – Sep 13, 2027 · 3 nights · Compare return dates departing Sep 10, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $399
Sep 10, 2027 – Sep 13, 2027 · 3 nights · Compare return dates departing Sep 10, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $432
Sep 11, 2027 – Sep 18, 2027 · 7 nights · Compare return dates departing Sep 11, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $399
Sep 11, 2027 – Sep 18, 2027 · 7 nights · Compare return dates departing Sep 11, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $432

Chicago (MDW) to Puerto Vallarta (PVR): October 2027

Travel dates Airline Stops Total price
Oct 1, 2027 – Oct 4, 2027 · 3 nights · Compare return dates departing Oct 1, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $420
Oct 1, 2027 – Oct 4, 2027 · 3 nights · Compare return dates departing Oct 1, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $455
Oct 2, 2027 – Oct 9, 2027 · 7 nights · Compare return dates departing Oct 2, 2027 Southwest Airlines Up to 1 stop each way Axel-exclusive $420
Oct 2, 2027 – Oct 9, 2027 · 7 nights · Compare return dates departing Oct 2, 2027 Delta Air Lines Up to 1 stop each way Axel-exclusive $455

Hotels in Puerto Vallarta for these trips

Hotels: under a trip, hotels in Puerto Vallarta 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.

All hotels in Puerto Vallarta

Route overview: Chicago to Puerto Vallarta (PVR) flight deals

2026-11-24 → 2026-11-29 · Axel-exclusive $558

2026-11-24 → 2026-11-29 · Axel-exclusive $612

2026-12-01 · one way · Axel-exclusive $250

2026-12-01 · one way · Axel-exclusive $275

2026-12-05 → 2026-12-12 · Axel-exclusive $465

2026-12-05 → 2026-12-12 · Axel-exclusive $510

2026-12-19 → 2026-12-26 · Axel-exclusive $651

2026-12-19 → 2026-12-26 · Axel-exclusive $714

2026-12-31 → 2027-01-03 · Axel-exclusive $651

2026-12-31 → 2027-01-03 · Axel-exclusive $714

2027-01-14 → 2027-01-17 · Axel-exclusive $465

2027-01-14 → 2027-01-17 · Axel-exclusive $510

2027-01-28 → 2027-01-31 · Axel-exclusive $465

2027-01-28 → 2027-01-31 · Axel-exclusive $510

2027-02-11 → 2027-02-14 · Axel-exclusive $500

2027-02-11 → 2027-02-14 · Axel-exclusive $548

2027-03-26 → 2027-03-29 · Axel-exclusive $513

2027-03-26 → 2027-03-29 · Axel-exclusive $560

2027-05-28 → 2027-05-31 · Axel-exclusive $462

2027-05-28 → 2027-05-31 · Axel-exclusive $501

2027-08-13 → 2027-08-16 · Axel-exclusive $420

2027-08-13 → 2027-08-16 · Axel-exclusive $455

2027-10-02 → 2027-10-09 · Axel-exclusive $420

2027-10-02 → 2027-10-09 · Axel-exclusive $455

More dates for this route

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