Lowcost flights from Chicago (United States) to San Juan (Puerto Rico), €83 - €331

Direct distance between cities: 3306 km. Average direct flight time is 4:53 hours.

Please note! Some routes are seasonal.

From Chicago to San Juan with Fly Arna (G6)
From Chicago to San Juan with Spirit Airlines (NK)
From Chicago to San Juan with Southwest Airlines (WN)
Average ticket price: €83 - €331

Connection in Atlanta (United States)
From Chicago to Atlanta with Frontier Airlines (F9)
From Chicago to Atlanta with Southwest Airlines (WN)
From Chicago to Atlanta with Fly Lili (FL)
From Chicago to Atlanta with Level (IB)
Average ticket price: €24 - €95
From Atlanta to San Juan with Southwest Airlines (WN)
From Atlanta to San Juan with Spirit Airlines (NK)
From Atlanta to San Juan with Fly Lili (FL)
Average ticket price: €62 - €249
Connection in Atlantic City (United States)
From Chicago to Atlantic City with Spirit Airlines (NK)
Average ticket price: €29 - €115
From Atlantic City to San Juan with Spirit Airlines (NK)
Average ticket price: €61 - €246
Connection in Austin (United States)
From Chicago to Austin with Southwest Airlines (WN)
From Chicago to Austin with Fly Lili (FL)
From Chicago to Austin with Level (IB)
Average ticket price: €39 - €158
From Austin to San Juan with Southwest Airlines (WN)
Average ticket price: €86 - €345
Connection in Baltimore (United States)
From Chicago to Baltimore with Frontier Airlines (F9)
From Chicago to Baltimore with Southwest Airlines (WN)
From Chicago to Baltimore with Fly Lili (FL)
Average ticket price: €24 - €97
From Baltimore to San Juan with Southwest Airlines (WN)
From Baltimore to San Juan with Spirit Airlines (NK)
From Baltimore to San Juan with Fly Lili (FL)
Average ticket price: €63 - €253
Connection in Boston (United States)
From Chicago to Boston with Southwest Airlines (WN)
From Chicago to Boston with Spirit Airlines (NK)
From Chicago to Boston with Fly Lili (FL)
From Chicago to Boston with Level (IB)
Average ticket price: €34 - €137
From Boston to San Juan with Frontier Airlines (F9)
Average ticket price: €67 - €270
Connection in Charlotte (United States)
From Chicago to Charlotte with Frontier Airlines (F9)
From Chicago to Charlotte with Southwest Airlines (WN)
From Chicago to Charlotte with Fly Lili (FL)
Average ticket price: €24 - €95
From Charlotte to San Juan with Frontier Airlines (F9)
Average ticket price: €59 - €236
Connection in Dallas (United States)
From Chicago to Dallas with Gol Transportes Aéreos (G3)
From Chicago to Dallas with Frontier Airlines (F9)
From Chicago to Dallas with Southwest Airlines (WN)
From Chicago to Dallas with Spirit Airlines (NK)
Average ticket price: €32 - €129
From Dallas to San Juan with Spirit Airlines (NK)
Average ticket price: €86 - €345
Connection in Fort Lauderdale (United States)
From Chicago to Fort Lauderdale with Southwest Airlines (WN)
From Chicago to Fort Lauderdale with Spirit Airlines (NK)
Average ticket price: €47 - €188
From Fort Lauderdale to San Juan with Frontier Airlines (F9)
From Fort Lauderdale to San Juan with Southwest Airlines (WN)
From Fort Lauderdale to San Juan with Spirit Airlines (NK)
From Fort Lauderdale to San Juan with Fly Lili (FL)
Average ticket price: €42 - €168
Connection in Hartford (United States)
From Chicago to Hartford with Southwest Airlines (WN)
From Chicago to Hartford with Fly Lili (FL)
Average ticket price: €31 - €124
From Hartford to San Juan with Frontier Airlines (F9)
Average ticket price: €67 - €268
Connection in Houston (United States)
From Chicago to Houston with Frontier Airlines (F9)
From Chicago to Houston with Southwest Airlines (WN)
From Chicago to Houston with Spirit Airlines (NK)
From Chicago to Houston with Fly Lili (FL)
Average ticket price: €38 - €152
From Houston to San Juan with Southwest Airlines (WN)
From Houston to San Juan with Spirit Airlines (NK)
Average ticket price: €80 - €321
Connection in Madrid (Spain)
From Chicago to Madrid with Level (IB)
Average ticket price: €168 - €673
From Madrid to San Juan with Level (IB)
Average ticket price: €159 - €637
Connection in Miami (United States)
From Chicago to Miami with Gol Transportes Aéreos (G3)
From Chicago to Miami with Frontier Airlines (F9)
From Chicago to Miami with Southwest Airlines (WN)
From Chicago to Miami with Spirit Airlines (NK)
From Chicago to Miami with Fly Arna (G6)
Average ticket price: €48 - €191
From Miami to San Juan with Frontier Airlines (F9)
From Miami to San Juan with Spirit Airlines (NK)
From Miami to San Juan with Level (IB)
Average ticket price: €42 - €167
Connection in Minneapolis (United States)
From Chicago to Minneapolis with Southwest Airlines (WN)
From Chicago to Minneapolis with Spirit Airlines (NK)
From Chicago to Minneapolis with Sun Country Airlines (SY)
From Chicago to Minneapolis with Fly Lili (FL)
Average ticket price: €14 - €57
From Minneapolis to San Juan with Sun Country Airlines (SY)
Average ticket price: €97 - €387
Connection in Nashville (United States)
From Chicago to Nashville with Allegiant Air (G4)
From Chicago to Nashville with Frontier Airlines (F9)
From Chicago to Nashville with Southwest Airlines (WN)
From Chicago to Nashville with Fly Lili (FL)
From Chicago to Nashville with Level (IB)
Average ticket price: €16 - €65
From Nashville to San Juan with Southwest Airlines (WN)
Average ticket price: €70 - €281
Connection in New Haven (United States)
From Chicago to New Haven with Avelo Airlines (XP)
Average ticket price: €31 - €122
From New Haven to San Juan with Avelo Airlines (XP)
Average ticket price: €66 - €262
Connection in New Orleans (United States)
From Chicago to New Orleans with Breeze Airways (MX)
From Chicago to New Orleans with Southwest Airlines (WN)
From Chicago to New Orleans with Spirit Airlines (NK)
From Chicago to New Orleans with Fly Lili (FL)
From Chicago to New Orleans with Level (IB)
Average ticket price: €34 - €134
From New Orleans to San Juan with Spirit Airlines (NK)
Average ticket price: €68 - €274
Connection in New York (United States)
From Chicago to New York with Gol Transportes Aéreos (G3)
From Chicago to New York with Southwest Airlines (WN)
From Chicago to New York with Spirit Airlines (NK)
From Chicago to New York with Fly Lili (FL)
Average ticket price: €29 - €115
From New York to San Juan with Frontier Airlines (F9)
Average ticket price: €65 - €259
Connection in Orlando (United States)
From Chicago to Orlando with Gol Transportes Aéreos (G3)
From Chicago to Orlando with Allegiant Air (G4)
From Chicago to Orlando with Frontier Airlines (F9)
From Chicago to Orlando with Southwest Airlines (WN)
From Chicago to Orlando with Spirit Airlines (NK)
From Chicago to Orlando with Fly Lili (FL)
Average ticket price: €40 - €159
From Orlando to San Juan with Southwest Airlines (WN)
From Orlando to San Juan with Spirit Airlines (NK)
From Orlando to San Juan with Fly Lili (FL)
Average ticket price: €48 - €192
Connection in Philadelphia (United States)
From Chicago to Philadelphia with Frontier Airlines (F9)
From Chicago to Philadelphia with Southwest Airlines (WN)
From Chicago to Philadelphia with Fly Lili (FL)
Average ticket price: €27 - €107
From Philadelphia to San Juan with Frontier Airlines (F9)
From Philadelphia to San Juan with Spirit Airlines (NK)
Average ticket price: €64 - €254
Connection in Punta Cana (Dominican Republic)
From Chicago to Punta Cana with Frontier Airlines (F9)
From Chicago to Punta Cana with Fly Lili (FL)
Average ticket price: €79 - €317
From Punta Cana to San Juan with Frontier Airlines (F9)
Average ticket price: €6 - €24
Connection in Raleigh/Durham (United States)
From Chicago to Raleigh/Durham with Frontier Airlines (F9)
From Chicago to Raleigh/Durham with Southwest Airlines (WN)
From Chicago to Raleigh/Durham with Fly Lili (FL)
Average ticket price: €25 - €102
From Raleigh/Durham to San Juan with Frontier Airlines (F9)
Average ticket price: €58 - €230
Connection in Saint Louis (United States)
From Chicago to Saint Louis with Southwest Airlines (WN)
From Chicago to Saint Louis with Fly Lili (FL)
Average ticket price: €11 - €42
From Saint Louis to San Juan with Southwest Airlines (WN)
Average ticket price: €81 - €323
Connection in Tampa (United States)
From Chicago to Tampa with Allegiant Air (G4)
From Chicago to Tampa with Frontier Airlines (F9)
From Chicago to Tampa with Southwest Airlines (WN)
From Chicago to Tampa with Spirit Airlines (NK)
From Chicago to Tampa with Fly Lili (FL)
Average ticket price: €40 - €162
From Tampa to San Juan with Frontier Airlines (F9)
From Tampa to San Juan with Southwest Airlines (WN)
From Tampa to San Juan with Fly Lili (FL)
Average ticket price: €49 - €197
Connection in Toronto (Canada)
From Chicago to Toronto with Level (IB)
Average ticket price: €18 - €70
From Toronto to San Juan with Air Canada Rouge (RV)
Average ticket price: €77 - €306
Connection in Wilmington (United States)
From Chicago to Wilmington with Frontier Airlines (F9)
Average ticket price: €26 - €104
From Wilmington to San Juan with Avelo Airlines (XP)
Average ticket price: €63 - €253