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

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

Please note! Some routes are seasonal.

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

Connection in Atlanta (United States)
From San Juan to Atlanta with Southwest Airlines (WN)
From San Juan to Atlanta with Spirit Airlines (NK)
From San Juan to Atlanta with Fly Lili (FL)
Average ticket price: €62 - €249
From Atlanta to Chicago with Frontier Airlines (F9)
From Atlanta to Chicago with Southwest Airlines (WN)
From Atlanta to Chicago with Fly Lili (FL)
From Atlanta to Chicago with Level (IB)
Average ticket price: €24 - €95
Connection in Austin (United States)
From San Juan to Austin with Southwest Airlines (WN)
Average ticket price: €86 - €345
From Austin to Chicago with Southwest Airlines (WN)
From Austin to Chicago with Fly Lili (FL)
From Austin to Chicago with Level (IB)
Average ticket price: €39 - €158
Connection in Baltimore (United States)
From San Juan to Baltimore with Southwest Airlines (WN)
From San Juan to Baltimore with Spirit Airlines (NK)
From San Juan to Baltimore with Fly Lili (FL)
Average ticket price: €63 - €253
From Baltimore to Chicago with Frontier Airlines (F9)
From Baltimore to Chicago with Southwest Airlines (WN)
From Baltimore to Chicago with Fly Lili (FL)
Average ticket price: €24 - €97
Connection in Dallas (United States)
From San Juan to Dallas with Spirit Airlines (NK)
Average ticket price: €86 - €345
From Dallas to Chicago with Gol Transportes Aéreos (G3)
From Dallas to Chicago with Frontier Airlines (F9)
From Dallas to Chicago with Southwest Airlines (WN)
From Dallas to Chicago with Spirit Airlines (NK)
From Dallas to Chicago with Level (IB)
Average ticket price: €32 - €129
Connection in Fort Lauderdale (United States)
From San Juan to Fort Lauderdale with Southwest Airlines (WN)
From San Juan to Fort Lauderdale with Spirit Airlines (NK)
From San Juan to Fort Lauderdale with Fly Lili (FL)
Average ticket price: €42 - €168
From Fort Lauderdale to Chicago with Southwest Airlines (WN)
From Fort Lauderdale to Chicago with Spirit Airlines (NK)
Average ticket price: €47 - €188
Connection in Houston (United States)
From San Juan to Houston with Southwest Airlines (WN)
From San Juan to Houston with Spirit Airlines (NK)
Average ticket price: €80 - €321
From Houston to Chicago with Frontier Airlines (F9)
From Houston to Chicago with Southwest Airlines (WN)
From Houston to Chicago with Spirit Airlines (NK)
From Houston to Chicago with Fly Lili (FL)
From Houston to Chicago with Level (IB)
Average ticket price: €38 - €152
Connection in Madrid (Spain)
From San Juan to Madrid with Level (IB)
Average ticket price: €159 - €637
From Madrid to Chicago with Level (IB)
Average ticket price: €168 - €673
Connection in Miami (United States)
From San Juan to Miami with Spirit Airlines (NK)
From San Juan to Miami with Level (IB)
Average ticket price: €42 - €167
From Miami to Chicago with Gol Transportes Aéreos (G3)
From Miami to Chicago with Frontier Airlines (F9)
From Miami to Chicago with Southwest Airlines (WN)
From Miami to Chicago with Spirit Airlines (NK)
Average ticket price: €48 - €191
Connection in Minneapolis (United States)
From San Juan to Minneapolis with Sun Country Airlines (SY)
Average ticket price: €97 - €387
From Minneapolis to Chicago with Southwest Airlines (WN)
From Minneapolis to Chicago with Spirit Airlines (NK)
From Minneapolis to Chicago with Sun Country Airlines (SY)
From Minneapolis to Chicago with Fly Lili (FL)
From Minneapolis to Chicago with Level (IB)
Average ticket price: €14 - €57
Connection in Nashville (United States)
From San Juan to Nashville with Southwest Airlines (WN)
Average ticket price: €70 - €281
From Nashville to Chicago with Allegiant Air (G4)
From Nashville to Chicago with Frontier Airlines (F9)
From Nashville to Chicago with Southwest Airlines (WN)
From Nashville to Chicago with Fly Lili (FL)
From Nashville to Chicago with Level (IB)
Average ticket price: €16 - €65
Connection in New Haven (United States)
From San Juan to New Haven with Avelo Airlines (XP)
Average ticket price: €66 - €262
From New Haven to Chicago with Avelo Airlines (XP)
Average ticket price: €31 - €122
Connection in New Orleans (United States)
From San Juan to New Orleans with Spirit Airlines (NK)
Average ticket price: €68 - €274
From New Orleans to Chicago with Breeze Airways (MX)
From New Orleans to Chicago with Southwest Airlines (WN)
From New Orleans to Chicago with Spirit Airlines (NK)
From New Orleans to Chicago with Fly Lili (FL)
Average ticket price: €34 - €134
Connection in Ontario (United States)
From San Juan to Ontario with Fly Lili (FL)
Average ticket price: €134 - €536
From Ontario to Chicago with Southwest Airlines (WN)
Average ticket price: €69 - €276
Connection in Orlando (United States)
From San Juan to Orlando with Southwest Airlines (WN)
From San Juan to Orlando with Spirit Airlines (NK)
From San Juan to Orlando with Fly Lili (FL)
Average ticket price: €48 - €192
From Orlando to Chicago with Gol Transportes Aéreos (G3)
From Orlando to Chicago with Allegiant Air (G4)
From Orlando to Chicago with Southwest Airlines (WN)
From Orlando to Chicago with Spirit Airlines (NK)
From Orlando to Chicago with Fly Lili (FL)
From Orlando to Chicago with Level (IB)
Average ticket price: €40 - €159
Connection in Philadelphia (United States)
From San Juan to Philadelphia with Spirit Airlines (NK)
Average ticket price: €64 - €254
From Philadelphia to Chicago with Frontier Airlines (F9)
From Philadelphia to Chicago with Southwest Airlines (WN)
From Philadelphia to Chicago with Fly Lili (FL)
From Philadelphia to Chicago with Level (IB)
Average ticket price: €27 - €107
Connection in Punta Cana (Dominican Republic)
From San Juan to Punta Cana with Frontier Airlines (F9)
From San Juan to Punta Cana with Southwest Airlines (WN)
Average ticket price: €6 - €24
From Punta Cana to Chicago with Frontier Airlines (F9)
From Punta Cana to Chicago with Fly Lili (FL)
Average ticket price: €79 - €317
Connection in Raleigh/Durham (United States)
From San Juan to Raleigh/Durham with Frontier Airlines (F9)
Average ticket price: €58 - €230
From Raleigh/Durham to Chicago with Frontier Airlines (F9)
From Raleigh/Durham to Chicago with Southwest Airlines (WN)
From Raleigh/Durham to Chicago with Fly Lili (FL)
Average ticket price: €25 - €102
Connection in Saint Louis (United States)
From San Juan to Saint Louis with Southwest Airlines (WN)
Average ticket price: €81 - €323
From Saint Louis to Chicago with Southwest Airlines (WN)
From Saint Louis to Chicago with Sun Country Airlines (SY)
From Saint Louis to Chicago with Fly Lili (FL)
Average ticket price: €11 - €42
Connection in Tampa (United States)
From San Juan to Tampa with Frontier Airlines (F9)
From San Juan to Tampa with Southwest Airlines (WN)
From San Juan to Tampa with Fly Lili (FL)
Average ticket price: €49 - €197
From Tampa to Chicago with Allegiant Air (G4)
From Tampa to Chicago with Frontier Airlines (F9)
From Tampa to Chicago with Southwest Airlines (WN)
From Tampa to Chicago with Spirit Airlines (NK)
From Tampa to Chicago with Fly Lili (FL)
Average ticket price: €40 - €162
Connection in Toronto (Canada)
From San Juan to Toronto with Air Canada Rouge (RV)
Average ticket price: €77 - €306
From Toronto to Chicago with Level (IB)
Average ticket price: €18 - €70
Connection in Wilmington (United States)
From San Juan to Wilmington with Avelo Airlines (XP)
Average ticket price: €63 - €253
From Wilmington to Chicago with Frontier Airlines (F9)
Average ticket price: €26 - €104