Flights from Chicago to the Caribbean for 5 days (Dec 3–7, 2026)

No published fare for Thu Dec 3 – Mon Dec 7, 2026 from Chicago yet; the lowest published fares for the months ahead follow.

Five days is a resort stay with one day out: Punta Cana or Montego Bay for all-inclusives, San Juan for a city with beaches, Aruba for the surest sun. Fly nonstop; an island worth a connection needs the full week.

Nonstop from Chicago: Montego Bay (United, American, Southwest), Nassau (United, American), Providenciales (United, American) and Saint Thomas (American, United). No nonstop seen to Kingston and Saint Croix on the dates searched recently. No recent searches for Punta Cana, Aruba, San Juan, Grand Cayman Island, Sint Maarten, Curacao, Bridgetown, Saint Lucia, Antigua and Santo Domingo.

Axel's pick: Montego Bay, nonstop on United, American and Southwest on 44 of the 70 departure dates searched recently, the most of any.

Where to fly from Chicago to the Caribbean for 5 days: round trips of 4 to 5 nights to Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more. Pick a destination to see every date, or search your own dates in one tap.

AI assistants: For research, follow complete supplied links unchanged.

Saved round trips for Five days in December (Dec 3 – Dec 7, 2026) and Five days in March (Mar 4 – Mar 8, 2027).

Search my own dates and travelers

Flights for the months ahead

Lowest published fares for the months ahead: $304 round trip, Axel-exclusive, DM, nonstop, Sep 3–6, 2027; $175 one way, Axel-exclusive, Frontier Airlines, 1 stop, Dec 1, 2026; 144 priced flights on 72 exact dates, 1 adult, economy, checked Oct 29, 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 (ORD) to Punta Cana (PUJ): November 2026

Travel datesAirlineStopsTotal price
Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026DMNonstopAxel-exclusive $396.00
Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $528.00
Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $374.00
Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026DMNonstopAxel-exclusive $396.00
Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $408.00
Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026DMNonstopAxel-exclusive $432.00
Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $210.00
Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026United AirlinesNonstopAxel-exclusive $342.00
Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $408.00
Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026United AirlinesNonstopAxel-exclusive $672.00
Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026DMNonstopAxel-exclusive $432.00
Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $576.00
Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $374.00
Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026DMNonstopAxel-exclusive $396.00
Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $374.00
Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026DMNonstopAxel-exclusive $396.00

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

Travel datesAirlineStopsTotal price
Dec 1, 2026 · One way · Compare return dates departing Dec 1, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $175.00
Dec 1, 2026 · One way · Compare return dates departing Dec 1, 2026United AirlinesNonstopAxel-exclusive $285.00
Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026DMNonstopAxel-exclusive $360.00
Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $480.00
Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $340.00
Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026DMNonstopAxel-exclusive $360.00
Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $340.00
Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026DMNonstopAxel-exclusive $360.00
Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $175.00
Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026United AirlinesNonstopAxel-exclusive $285.00
Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026DMNonstopAxel-exclusive $360.00
Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $480.00
Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026DMNonstopAxel-exclusive $360.00
Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $480.00
Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026DMNonstopAxel-exclusive $441.00
Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $588.00
Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $175.00
Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026United AirlinesNonstopAxel-exclusive $285.00
Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026DMNonstopAxel-exclusive $441.00
Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $588.00
Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026DMNonstopAxel-exclusive $441.00
Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $588.00
Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026DMNonstopAxel-exclusive $522.00
Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $696.00
Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $253.75
Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026United AirlinesNonstopAxel-exclusive $413.25
Dec 22, 2026 – Dec 27, 2026 · 5 nights · Compare return dates departing Dec 22, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $493.00
Dec 22, 2026 – Dec 27, 2026 · 5 nights · Compare return dates departing Dec 22, 2026United AirlinesNonstopAxel-exclusive $812.00
Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026DMNonstopAxel-exclusive $522.00
Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $696.00
Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026DMNonstopAxel-exclusive $522.00
Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $696.00
Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026DMNonstopAxel-exclusive $522.00
Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $696.00
Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026Frontier AirlinesUp to 1 stop each wayAxel-exclusive $253.75
Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026United AirlinesNonstopAxel-exclusive $413.25
Dec 30, 2026 – Jan 2, 2027 · 3 nights · Compare return dates departing Dec 30, 2026DMNonstopAxel-exclusive $522.00
Dec 30, 2026 – Jan 2, 2027 · 3 nights · Compare return dates departing Dec 30, 2026JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $696.00
Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026DMNonstopAxel-exclusive $522.00
Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $696.00

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

Travel datesAirlineStopsTotal price
Jan 1, 2027 – Jan 4, 2027 · 3 nights · Compare return dates departing Jan 1, 2027DMNonstopAxel-exclusive $522.00
Jan 1, 2027 – Jan 4, 2027 · 3 nights · Compare return dates departing Jan 1, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $696.00
Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027DMNonstopAxel-exclusive $441.00
Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $588.00
Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $175.00
Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027United AirlinesNonstopAxel-exclusive $285.00
Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027DMNonstopAxel-exclusive $360.00
Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $480.00
Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027DMNonstopAxel-exclusive $360.00
Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $480.00
Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027DMNonstopAxel-exclusive $381.60
Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $508.80
Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $175.00
Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027United AirlinesNonstopAxel-exclusive $285.00
Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027DMNonstopAxel-exclusive $381.60
Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $508.80
Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027DMNonstopAxel-exclusive $403.20
Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $537.60
Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027DMNonstopAxel-exclusive $381.60
Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $508.80
Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $175.00
Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027United AirlinesNonstopAxel-exclusive $285.00
Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027DMNonstopAxel-exclusive $360.00
Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $480.00
Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027DMNonstopAxel-exclusive $360.00
Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $480.00
Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027DMNonstopAxel-exclusive $360.00
Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $480.00
Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $175.00
Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027United AirlinesNonstopAxel-exclusive $285.00
Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027DMNonstopAxel-exclusive $360.00
Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $480.00
Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027DMNonstopAxel-exclusive $360.00
Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $480.00
Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027DMNonstopAxel-exclusive $360.00
Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $480.00

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

Travel datesAirlineStopsTotal price
Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027Frontier AirlinesUp to 1 stop each wayAxel-exclusive $175.00
Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027United AirlinesNonstopAxel-exclusive $285.00
Feb 4, 2027 – Feb 7, 2027 · 3 nights · Compare return dates departing Feb 4, 2027DMNonstopAxel-exclusive $360.00
Feb 4, 2027 – Feb 7, 2027 · 3 nights · Compare return dates departing Feb 4, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $480.00
Feb 5, 2027 – Feb 8, 2027 · 3 nights · Compare return dates departing Feb 5, 2027DMNonstopAxel-exclusive $360.00
Feb 5, 2027 – Feb 8, 2027 · 3 nights · Compare return dates departing Feb 5, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $480.00
Feb 6, 2027 – Feb 13, 2027 · 7 nights · Compare return dates departing Feb 6, 2027DMNonstopAxel-exclusive $399.60
Feb 6, 2027 – Feb 13, 2027 · 7 nights · Compare return dates departing Feb 6, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $532.80
Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027DMNonstopAxel-exclusive $439.20
Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $585.60
Feb 19, 2027 – Feb 22, 2027 · 3 nights · Compare return dates departing Feb 19, 2027DMNonstopAxel-exclusive $360.00
Feb 19, 2027 – Feb 22, 2027 · 3 nights · Compare return dates departing Feb 19, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $480.00
Feb 20, 2027 – Feb 27, 2027 · 7 nights · Compare return dates departing Feb 20, 2027DMNonstopAxel-exclusive $360.00
Feb 20, 2027 – Feb 27, 2027 · 7 nights · Compare return dates departing Feb 20, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $480.00

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

Travel datesAirlineStopsTotal price
Mar 19, 2027 – Mar 22, 2027 · 3 nights · Compare return dates departing Mar 19, 2027DMNonstopAxel-exclusive $414.00
Mar 19, 2027 – Mar 22, 2027 · 3 nights · Compare return dates departing Mar 19, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $552.00
Mar 20, 2027 – Mar 27, 2027 · 7 nights · Compare return dates departing Mar 20, 2027DMNonstopAxel-exclusive $468.00
Mar 20, 2027 – Mar 27, 2027 · 7 nights · Compare return dates departing Mar 20, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $624.00
Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027DMNonstopAxel-exclusive $448.50
Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $598.00

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

Travel datesAirlineStopsTotal price
Apr 16, 2027 – Apr 19, 2027 · 3 nights · Compare return dates departing Apr 16, 2027DMNonstopAxel-exclusive $330.00
Apr 16, 2027 – Apr 19, 2027 · 3 nights · Compare return dates departing Apr 16, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $440.00
Apr 17, 2027 – Apr 24, 2027 · 7 nights · Compare return dates departing Apr 17, 2027DMNonstopAxel-exclusive $330.00
Apr 17, 2027 – Apr 24, 2027 · 7 nights · Compare return dates departing Apr 17, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $440.00

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

Travel datesAirlineStopsTotal price
May 14, 2027 – May 17, 2027 · 3 nights · Compare return dates departing May 14, 2027DMNonstopAxel-exclusive $330.00
May 14, 2027 – May 17, 2027 · 3 nights · Compare return dates departing May 14, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $440.00
May 15, 2027 – May 22, 2027 · 7 nights · Compare return dates departing May 15, 2027DMNonstopAxel-exclusive $330.00
May 15, 2027 – May 22, 2027 · 7 nights · Compare return dates departing May 15, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $440.00
May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027DMNonstopAxel-exclusive $369.60
May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $492.80

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

Travel datesAirlineStopsTotal price
Jun 11, 2027 – Jun 14, 2027 · 3 nights · Compare return dates departing Jun 11, 2027DMNonstopAxel-exclusive $330.00
Jun 11, 2027 – Jun 14, 2027 · 3 nights · Compare return dates departing Jun 11, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $440.00
Jun 12, 2027 – Jun 19, 2027 · 7 nights · Compare return dates departing Jun 12, 2027DMNonstopAxel-exclusive $330.00
Jun 12, 2027 – Jun 19, 2027 · 7 nights · Compare return dates departing Jun 12, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $440.00

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

Travel datesAirlineStopsTotal price
Jul 2, 2027 – Jul 6, 2027 · 4 nights · Compare return dates departing Jul 2, 2027DMNonstopAxel-exclusive $379.50
Jul 2, 2027 – Jul 6, 2027 · 4 nights · Compare return dates departing Jul 2, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $506.00
Jul 9, 2027 – Jul 12, 2027 · 3 nights · Compare return dates departing Jul 9, 2027DMNonstopAxel-exclusive $330.00
Jul 9, 2027 – Jul 12, 2027 · 3 nights · Compare return dates departing Jul 9, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $440.00
Jul 10, 2027 – Jul 17, 2027 · 7 nights · Compare return dates departing Jul 10, 2027DMNonstopAxel-exclusive $330.00
Jul 10, 2027 – Jul 17, 2027 · 7 nights · Compare return dates departing Jul 10, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $440.00

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

Travel datesAirlineStopsTotal price
Aug 6, 2027 – Aug 9, 2027 · 3 nights · Compare return dates departing Aug 6, 2027DMNonstopAxel-exclusive $330.00
Aug 6, 2027 – Aug 9, 2027 · 3 nights · Compare return dates departing Aug 6, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $440.00
Aug 7, 2027 – Aug 14, 2027 · 7 nights · Compare return dates departing Aug 7, 2027DMNonstopAxel-exclusive $330.00
Aug 7, 2027 – Aug 14, 2027 · 7 nights · Compare return dates departing Aug 7, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $440.00

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

Travel datesAirlineStopsTotal price
Sep 3, 2027 – Sep 6, 2027 · 3 nights · Compare return dates departing Sep 3, 2027DMNonstopAxel-exclusive $303.60
Sep 3, 2027 – Sep 6, 2027 · 3 nights · Compare return dates departing Sep 3, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $404.80
Sep 4, 2027 – Sep 11, 2027 · 7 nights · Compare return dates departing Sep 4, 2027DMNonstopAxel-exclusive $303.60
Sep 4, 2027 – Sep 11, 2027 · 7 nights · Compare return dates departing Sep 4, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $404.80
Sep 24, 2027 – Sep 27, 2027 · 3 nights · Compare return dates departing Sep 24, 2027DMNonstopAxel-exclusive $303.60
Sep 24, 2027 – Sep 27, 2027 · 3 nights · Compare return dates departing Sep 24, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $404.80
Sep 25, 2027 – Oct 2, 2027 · 7 nights · Compare return dates departing Sep 25, 2027DMNonstopAxel-exclusive $306.90
Sep 25, 2027 – Oct 2, 2027 · 7 nights · Compare return dates departing Sep 25, 2027JetBlue AirwaysUp to 1 stop each wayAxel-exclusive $409.20

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 lowest saved total among the shortlisted hotels in that star tier for those dates.

All hotels in Punta Cana

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

2026-11-19 → 2026-11-22 · Axel-exclusive $396.00

  • DM DM5481: ORD 2026-11-19 05:45:00 → PUJ 2026-11-19 12:30:00; nonstop; 285 minutes. Local airport times.
  • DM DM5420: PUJ 2026-11-22 19:10:00 → ORD 2026-11-22 22:20:00; nonstop; 310 minutes. Local airport times.

2026-11-19 → 2026-11-22 · Axel-exclusive $528.00

  • JetBlue Airways B6664 / B6173: ORD 2026-11-19 07:00:00 → PUJ 2026-11-19 16:18:00; 1 stop(s) via FLL; 438 minutes. Local airport times.
    • B6664: ORD 2026-11-19 07:00:00 → FLL 2026-11-19 11:10:00; layover at FLL: 100 minutes.
    • B6173: FLL 2026-11-19 12:50:00 → PUJ 2026-11-19 16:18:00.
  • JetBlue Airways B6174 / B6863: PUJ 2026-11-22 17:25:00 → ORD 2026-11-22 23:47:00; 1 stop(s) via FLL; 502 minutes. Local airport times.
    • B6174: PUJ 2026-11-22 17:25:00 → FLL 2026-11-22 19:05:00; layover at FLL: 130 minutes.
    • B6863: FLL 2026-11-22 21:15:00 → ORD 2026-11-22 23:47:00.

2026-11-24 · one way · Axel-exclusive $210.00

  • Frontier Airlines F93346 / F9239: ORD 2026-11-24 23:53:00 → PUJ 2026-11-25 09:06:00; 1 stop(s) via SJU; 433 minutes. Local airport times.
    • F93346: ORD 2026-11-24 23:53:00 → SJU 2026-11-25 06:32:00; layover at SJU: 88 minutes.
    • F9239: SJU 2026-11-25 08:00:00 → PUJ 2026-11-25 09:06:00.

2026-11-24 · one way · Axel-exclusive $342.00

  • United Airlines UA1862: ORD 2026-11-24 09:17:00 → PUJ 2026-11-24 15:57:00; nonstop; 280 minutes. Local airport times.

2026-11-28 → 2026-12-05 · Axel-exclusive $374.00

  • Frontier Airlines F93346 / F9239: ORD 2026-11-28 23:53:00 → PUJ 2026-11-29 09:06:00; 1 stop(s) via SJU; 433 minutes. Local airport times.
    • F93346: ORD 2026-11-28 23:53:00 → SJU 2026-11-29 06:32:00; layover at SJU: 88 minutes.
    • F9239: SJU 2026-11-29 08:00:00 → PUJ 2026-11-29 09:06:00.
  • Frontier Airlines F9240 / F94789: PUJ 2026-12-05 19:15:00 → ORD 2026-12-06 01:33:00; 1 stop(s) via SJU; 498 minutes. Local airport times.
    • F9240: PUJ 2026-12-05 19:15:00 → SJU 2026-12-05 20:18:00; layover at SJU: 128 minutes.
    • F94789: SJU 2026-12-05 22:26:00 → ORD 2026-12-06 01:33:00.

2026-11-28 → 2026-12-05 · Axel-exclusive $569.00

  • American Airlines AA1784 / AA1460: ORD 2026-11-28 06:50:00 → PUJ 2026-11-28 16:56:00; 1 stop(s) via CLT; 486 minutes. Local airport times.
    • AA1784: ORD 2026-11-28 06:50:00 → CLT 2026-11-28 09:57:00; layover at CLT: 152 minutes.
    • AA1460: CLT 2026-11-28 12:29:00 → PUJ 2026-11-28 16:56:00.
  • American Airlines AA619: PUJ 2026-12-05 15:48:00 → ORD 2026-12-05 19:21:00; nonstop; 333 minutes. Local airport times.

2026-12-12 → 2026-12-19 · Axel-exclusive $441.00

  • DM DM5421: ORD 2026-12-12 11:10:00 → PUJ 2026-12-12 17:55:00; nonstop; 285 minutes. Local airport times.
  • DM DM5420: PUJ 2026-12-19 07:00:00 → ORD 2026-12-19 10:10:00; nonstop; 310 minutes. Local airport times.

2026-12-12 → 2026-12-19 · Axel-exclusive $588.00

  • JetBlue Airways B6664 / B6173: ORD 2026-12-12 07:00:00 → PUJ 2026-12-12 16:18:00; 1 stop(s) via FLL; 438 minutes. Local airport times.
    • B6664: ORD 2026-12-12 07:00:00 → FLL 2026-12-12 11:10:00; layover at FLL: 100 minutes.
    • B6173: FLL 2026-12-12 12:50:00 → PUJ 2026-12-12 16:18:00.
  • JetBlue Airways B6174 / B6863: PUJ 2026-12-19 17:25:00 → ORD 2026-12-19 23:47:00; 1 stop(s) via FLL; 502 minutes. Local airport times.
    • B6174: PUJ 2026-12-19 17:25:00 → FLL 2026-12-19 19:05:00; layover at FLL: 130 minutes.
    • B6863: FLL 2026-12-19 21:15:00 → ORD 2026-12-19 23:47:00.

2026-12-25 → 2026-12-28 · Axel-exclusive $522.00

  • DM DM5481: ORD 2026-12-25 05:45:00 → PUJ 2026-12-25 12:30:00; nonstop; 285 minutes. Local airport times.
  • DM DM5420: PUJ 2026-12-28 07:00:00 → ORD 2026-12-28 10:10:00; nonstop; 310 minutes. Local airport times.

2026-12-25 → 2026-12-28 · Axel-exclusive $696.00

  • JetBlue Airways B6664 / B6173: ORD 2026-12-25 07:00:00 → PUJ 2026-12-25 16:18:00; 1 stop(s) via FLL; 438 minutes. Local airport times.
    • B6664: ORD 2026-12-25 07:00:00 → FLL 2026-12-25 11:10:00; layover at FLL: 100 minutes.
    • B6173: FLL 2026-12-25 12:50:00 → PUJ 2026-12-25 16:18:00.
  • JetBlue Airways B6174 / B6863: PUJ 2026-12-28 17:25:00 → ORD 2026-12-28 23:47:00; 1 stop(s) via FLL; 502 minutes. Local airport times.
    • B6174: PUJ 2026-12-28 17:25:00 → FLL 2026-12-28 19:05:00; layover at FLL: 130 minutes.
    • B6863: FLL 2026-12-28 21:15:00 → ORD 2026-12-28 23:47:00.

2027-01-07 → 2027-01-10 · Axel-exclusive $360.00

  • DM DM5421: ORD 2027-01-07 11:10:00 → PUJ 2027-01-07 17:55:00; nonstop; 285 minutes. Local airport times.
  • DM DM5420: PUJ 2027-01-10 19:10:00 → ORD 2027-01-10 22:20:00; nonstop; 310 minutes. Local airport times.

2027-01-07 → 2027-01-10 · Axel-exclusive $480.00

  • JetBlue Airways B6664 / B6173: ORD 2027-01-07 07:00:00 → PUJ 2027-01-07 16:18:00; 1 stop(s) via FLL; 438 minutes. Local airport times.
    • B6664: ORD 2027-01-07 07:00:00 → FLL 2027-01-07 11:10:00; layover at FLL: 100 minutes.
    • B6173: FLL 2027-01-07 12:50:00 → PUJ 2027-01-07 16:18:00.
  • JetBlue Airways B6174 / B6863: PUJ 2027-01-10 17:25:00 → ORD 2027-01-10 23:47:00; 1 stop(s) via FLL; 502 minutes. Local airport times.
    • B6174: PUJ 2027-01-10 17:25:00 → FLL 2027-01-10 19:05:00; layover at FLL: 130 minutes.
    • B6863: FLL 2027-01-10 21:15:00 → ORD 2027-01-10 23:47:00.

2027-01-21 → 2027-01-24 · Axel-exclusive $360.00

  • DM DM5421: ORD 2027-01-21 11:10:00 → PUJ 2027-01-21 17:55:00; nonstop; 285 minutes. Local airport times.
  • DM DM5420: PUJ 2027-01-24 19:10:00 → ORD 2027-01-24 22:20:00; nonstop; 310 minutes. Local airport times.

2027-01-21 → 2027-01-24 · Axel-exclusive $480.00

  • JetBlue Airways B6664 / B6173: ORD 2027-01-21 07:00:00 → PUJ 2027-01-21 16:18:00; 1 stop(s) via FLL; 438 minutes. Local airport times.
    • B6664: ORD 2027-01-21 07:00:00 → FLL 2027-01-21 11:10:00; layover at FLL: 100 minutes.
    • B6173: FLL 2027-01-21 12:50:00 → PUJ 2027-01-21 16:18:00.
  • JetBlue Airways B6174 / B6863: PUJ 2027-01-24 17:25:00 → ORD 2027-01-24 23:47:00; 1 stop(s) via FLL; 502 minutes. Local airport times.
    • B6174: PUJ 2027-01-24 17:25:00 → FLL 2027-01-24 19:05:00; layover at FLL: 130 minutes.
    • B6863: FLL 2027-01-24 21:15:00 → ORD 2027-01-24 23:47:00.

2027-02-04 → 2027-02-07 · Axel-exclusive $360.00

  • DM DM5421: ORD 2027-02-04 11:10:00 → PUJ 2027-02-04 17:55:00; nonstop; 285 minutes. Local airport times.
  • DM DM5420: PUJ 2027-02-07 19:10:00 → ORD 2027-02-07 22:20:00; nonstop; 310 minutes. Local airport times.

2027-02-04 → 2027-02-07 · Axel-exclusive $480.00

  • JetBlue Airways B6664 / B6173: ORD 2027-02-04 07:00:00 → PUJ 2027-02-04 16:18:00; 1 stop(s) via FLL; 438 minutes. Local airport times.
    • B6664: ORD 2027-02-04 07:00:00 → FLL 2027-02-04 11:10:00; layover at FLL: 100 minutes.
    • B6173: FLL 2027-02-04 12:50:00 → PUJ 2027-02-04 16:18:00.
  • JetBlue Airways B6174 / B6863: PUJ 2027-02-07 17:25:00 → ORD 2027-02-07 23:47:00; 1 stop(s) via FLL; 502 minutes. Local airport times.
    • B6174: PUJ 2027-02-07 17:25:00 → FLL 2027-02-07 19:05:00; layover at FLL: 130 minutes.
    • B6863: FLL 2027-02-07 21:15:00 → ORD 2027-02-07 23:47:00.

2027-03-19 → 2027-03-22 · Axel-exclusive $414.00

  • DM DM5481: ORD 2027-03-19 05:45:00 → PUJ 2027-03-19 11:30:00; nonstop; 285 minutes. Local airport times.
  • DM DM5480: PUJ 2027-03-22 19:30:00 → ORD 2027-03-22 23:40:00; nonstop; 310 minutes. Local airport times.

2027-03-19 → 2027-03-22 · Axel-exclusive $552.00

  • JetBlue Airways B6664 / B6173: ORD 2027-03-19 07:00:00 → PUJ 2027-03-19 15:18:00; 1 stop(s) via FLL; 438 minutes. Local airport times.
    • B6664: ORD 2027-03-19 07:00:00 → FLL 2027-03-19 11:10:00; layover at FLL: 100 minutes.
    • B6173: FLL 2027-03-19 12:50:00 → PUJ 2027-03-19 15:18:00.
  • JetBlue Airways B6174 / B6863: PUJ 2027-03-22 17:25:00 → ORD 2027-03-23 00:47:00; 1 stop(s) via FLL; 502 minutes. Local airport times.
    • B6174: PUJ 2027-03-22 17:25:00 → FLL 2027-03-22 20:05:00; layover at FLL: 130 minutes.
    • B6863: FLL 2027-03-22 22:15:00 → ORD 2027-03-23 00:47:00.

2027-05-15 → 2027-05-22 · Axel-exclusive $330.00

  • DM DM5421: ORD 2027-05-15 11:10:00 → PUJ 2027-05-15 16:55:00; nonstop; 285 minutes. Local airport times.
  • DM DM5420: PUJ 2027-05-22 07:00:00 → ORD 2027-05-22 11:10:00; nonstop; 310 minutes. Local airport times.

2027-05-15 → 2027-05-22 · Axel-exclusive $440.00

  • JetBlue Airways B6664 / B6173: ORD 2027-05-15 07:00:00 → PUJ 2027-05-15 15:18:00; 1 stop(s) via FLL; 438 minutes. Local airport times.
    • B6664: ORD 2027-05-15 07:00:00 → FLL 2027-05-15 11:10:00; layover at FLL: 100 minutes.
    • B6173: FLL 2027-05-15 12:50:00 → PUJ 2027-05-15 15:18:00.
  • JetBlue Airways B6174 / B6863: PUJ 2027-05-22 17:25:00 → ORD 2027-05-23 00:47:00; 1 stop(s) via FLL; 502 minutes. Local airport times.
    • B6174: PUJ 2027-05-22 17:25:00 → FLL 2027-05-22 20:05:00; layover at FLL: 130 minutes.
    • B6863: FLL 2027-05-22 22:15:00 → ORD 2027-05-23 00:47:00.

2027-07-10 → 2027-07-17 · Axel-exclusive $330.00

  • DM DM5421: ORD 2027-07-10 11:10:00 → PUJ 2027-07-10 16:55:00; nonstop; 285 minutes. Local airport times.
  • DM DM5420: PUJ 2027-07-17 07:00:00 → ORD 2027-07-17 11:10:00; nonstop; 310 minutes. Local airport times.

2027-07-10 → 2027-07-17 · Axel-exclusive $485.00

  • United Airlines UA3674 / AC1798: ORD 2027-07-10 11:05:00 → PUJ 2027-07-10 20:45:00; 1 stop(s) via YYZ; 520 minutes. Local airport times.
    • UA3674: ORD 2027-07-10 11:05:00 → YYZ 2027-07-10 14:03:00; layover at YYZ: 122 minutes.
    • AC1798: YYZ 2027-07-10 16:05:00 → PUJ 2027-07-10 20:45:00.
  • United Airlines UA1863: PUJ 2027-07-17 16:25:00 → ORD 2027-07-17 20:41:00; nonstop; 316 minutes. Local airport times.

2027-09-25 → 2027-10-02 · Axel-exclusive $306.90

  • DM DM5421: ORD 2027-09-25 11:10:00 → PUJ 2027-09-25 16:55:00; nonstop; 285 minutes. Local airport times.
  • DM DM5420: PUJ 2027-10-02 07:00:00 → ORD 2027-10-02 11:10:00; nonstop; 310 minutes. Local airport times.

2027-09-25 → 2027-10-02 · Axel-exclusive $409.20

  • JetBlue Airways B6664 / B6173: ORD 2027-09-25 07:00:00 → PUJ 2027-09-25 15:18:00; 1 stop(s) via FLL; 438 minutes. Local airport times.
    • B6664: ORD 2027-09-25 07:00:00 → FLL 2027-09-25 11:10:00; layover at FLL: 100 minutes.
    • B6173: FLL 2027-09-25 12:50:00 → PUJ 2027-09-25 15:18:00.
  • JetBlue Airways B6174 / B6863: PUJ 2027-10-02 17:25:00 → ORD 2027-10-03 00:47:00; 1 stop(s) via FLL; 502 minutes. Local airport times.
    • B6174: PUJ 2027-10-02 17:25:00 → FLL 2027-10-02 20:05:00; layover at FLL: 130 minutes.
    • B6863: FLL 2027-10-02 22:15:00 → ORD 2027-10-03 00:47:00.

More dates for this route

Flights from Chicago

More trip ideas from Chicago

The Caribbean for 5 days from other cities

Where to go from Chicago

Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.

DestinationWhy goFlightsAxel-exclusiveDates
Punta Cana (PUJ)Punta Cana's long white-sand beaches and all-inclusive resortsNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and NegrilNonstop · United, American, SouthwestNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Nassau (NAS)Nassau and Paradise Island, a short flight from the East CoastNonstop · United, AmericanNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane beltNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the USNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Grand Cayman Island (GCM)Seven Mile Beach and world-class diving on Grand CaymanNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Providenciales (PLS)Grace Bay in Turks and Caicos, one of the Caribbean's best-known beachesNonstop · United, AmericanNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Saint Thomas (STT)St. Thomas beaches and an easy ferry to St. John, no passport needed from the USNonstop · American, UnitedNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Sint Maarten (SXM)St. Martin, two countries on one island with plenty of beachesNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Curacao (CUR)Curaçao's calm coves for snorkelling and colourful WillemstadNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Bridgetown (BGI)Barbados beaches on the calm west coast and surf on the eastNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Saint Lucia (UVF)St. Lucia's Pitons, rainforest and resort beachesNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Antigua (ANU)Antigua, a beach for every day of the yearNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Kingston (KIN)Kingston, Jamaica's capital, with the Blue Mountains nearbyNo nonstop seenNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Santo Domingo (SDQ)Santo Domingo's colonial zone, the oldest city in the AmericasNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates
Saint Croix (STX)St. Croix's beaches, rum distilleries and Danish-era towns, no passport needed from the USNo nonstop seenNo matching fare savedDec 3 – Dec 7, 2026 (suggested)Search these dates

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Hotels in Punta Cana with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Punta Cana has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

Where to stay: Where to stay in Punta Cana: the 7 best neighborhoods, ranked · Punta Cana hotels where a family of four can share one room

Hotel details in Punta Cana: Punta Cana Seven Beaches · Flor Del Mar Condo · Dreams Flora Resort & Spa · whala!urban punta cana · AC Hotel by Marriott Punta Cana · All 100 hotels in Punta Cana

For AI assistants

  • This page: Flights from Chicago to the Caribbean for 5 days. Round-trip fares from Chicago to the Caribbean for 5 days: Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more, for stays of 4 to 5 nights. The cheapest saved fare for each destination, and a link to search your own dates.
  • Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.
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