Cheapest Flights From Chicago

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Here’s the cheapest flights from Chicago across all of the USA. There’s cheap flights to Baltimore, Las Vegas, New York, Miami, Seattle, San Francisco and loads more. If you don’t see your destination or if you prefer to search your own flights, click any flight and adjust the cities and dates, or search any flight here ✈️.

The key is flexibility – don’t expect flight sales on a weekend in the school holidays. Do expect cheap flights midweek, when the weather is extreme and there’s few other tourists or no events on.

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Here’s the cheapest flights from Chicago for the next few months.

Origin - DestinationDeparture atReturn atPriceFind tickets
Chicago ↔ Tampa24 October 202127 October 2021 40 40
Chicago ↔ Fort Lauderdale26 October 202130 October 2021 41 41
Chicago ↔ Atlanta4 November 20219 November 2021 41 41
Chicago ↔ Myrtle Beach30 October 20211 November 2021 41 41
Chicago ↔ San Diego8 November 202111 November 2021 42 42
Chicago ↔ Las Vegas18 October 202121 October 2021 42 42
Chicago ↔ Orlando25 September 202128 September 2021 42 42
Chicago ↔ Miami2 October 20213 October 2021 43 43
Chicago ↔ Phoenix2 October 20214 October 2021 43 43
Chicago ↔ Fort Walton Beach23 September 202126 September 2021 46 46
Chicago ↔ Punta Gorda11 November 202114 November 2021 46 46
Chicago ↔ Fort Myers24 September 202130 September 2021 47 47
Chicago ↔ Dallas1 October 20214 October 2021 47 47
Chicago ↔ Houston30 September 20215 October 2021 52 52
Chicago ↔ New Orleans11 October 202116 October 2021 53 53
Chicago ↔ Los Angeles9 October 202112 October 2021 54 54
Chicago ↔ Denver12 October 202114 October 2021 63 63
Chicago ↔ Baltimore6 October 20219 October 2021 64 64
Chicago ↔ Santa Ana15 October 202118 October 2021 65 65
Chicago ↔ Philadelphia7 October 202111 October 2021 70 70
Chicago ↔ Oakland14 October 202116 October 2021 72 72
Chicago ↔ New York6 October 202110 October 2021 73 73
Chicago ↔ Boston27 October 202130 October 2021 76 76
Chicago ↔ Ontario24 September 202128 September 2021 78 78
Chicago ↔ Asheville14 October 202117 October 2021 81 81
Chicago ↔ Minneapolis16 October 202119 October 2021 83 83
Chicago ↔ Knoxville22 September 202123 September 2021 89 89
Chicago ↔ Hartford1 October 20213 October 2021 92 92
Chicago ↔ Austin24 September 202126 September 2021 92 92
Chicago ↔ Seattle28 September 20211 October 2021 97 97
Chicago ↔ Ronkonkoma13 October 202116 October 2021 98 98
Chicago ↔ Saint Croix31 October 20214 November 2021 98 98
Chicago ↔ Sacramento26 October 202130 October 2021 99 99
Chicago ↔ Columbus23 September 202128 September 2021 101 101
Chicago ↔ Pittsburgh6 November 20219 November 2021 101 101
Chicago ↔ San Juan6 October 202110 October 2021 102 102
Chicago ↔ Saint Thomas11 October 202115 October 2021 103 103
Chicago ↔ Memphis11 November 202115 November 2021 110 110
Chicago ↔ Washington4 November 20216 November 2021 110 110
Chicago ↔ Charlotte10 December 202113 December 2021 110 110
Chicago ↔ San Francisco23 September 202127 September 2021 112 112
Chicago ↔ Colorado Springs21 September 202127 September 2021 113 113
Chicago ↔ Dayton28 September 202130 September 2021 116 116
Chicago ↔ Indianapolis28 September 202129 September 2021 116 116
Chicago ↔ Portland21 September 202125 September 2021 118 118
Chicago ↔ Raleigh/Durham24 September 202127 September 2021 121 121
Chicago ↔ Nashville28 October 202131 October 2021 123 123
Chicago ↔ Detroit15 October 202116 October 2021 125 125
Chicago ↔ Saint Louis28 October 202131 October 2021 127 127
Chicago ↔ Kansas City15 October 202118 October 2021 127 127
Chicago ↔ Cincinnati8 November 202110 November 2021 127 127
Chicago ↔ Greensboro/High Point30 September 20214 October 2021 128 128
Chicago ↔ Sarasota9 December 202112 December 2021 135 135
Chicago ↔ Salt Lake City11 October 202115 October 2021 135 135
Chicago ↔ Cleveland24 September 202126 September 2021 137 137
Chicago ↔ Buffalo11 October 202112 October 2021 139 139
Chicago ↔ Peoria24 September 202127 September 2021 140 140
Chicago ↔ Guatemala City23 September 202124 September 2021 142 142
Chicago ↔ Albuquerque16 October 202118 October 2021 142 142
Chicago ↔ Cancun15 October 202120 October 2021 143 143
Chicago ↔ Providence6 November 20218 November 2021 143 143
Chicago ↔ San Antonio1 October 20214 October 2021 145 145
Chicago ↔ Norfolk24 September 202126 September 2021 147 147
Chicago ↔ Richmond21 October 202125 October 2021 149 149
Chicago ↔ Barranquilla5 November 20218 November 2021 160 160
Chicago ↔ Jacksonville7 October 202112 October 2021 163 163
Chicago ↔ El Paso11 November 202114 November 2021 167 167
Chicago ↔ San Jose9 October 202114 October 2021 168 168
Chicago ↔ Little Rock30 October 20211 November 2021 168 168
Chicago ↔ Savannah1 October 20213 October 2021 170 170
Chicago ↔ Grand Rapids1 October 20213 October 2021 172 172
Chicago ↔ Greenville12 November 202113 November 2021 174 174
Chicago ↔ Mobile15 October 202118 October 2021 174 174
Chicago ↔ Fayetteville28 October 202130 October 2021 175 175
Chicago ↔ Reno4 October 20217 October 2021 175 175
Chicago ↔ Lexington24 September 202126 September 2021 175 175
Chicago ↔ Cartagena30 October 20213 November 2021 177 177
Chicago ↔ Tulsa28 October 202129 October 2021 178 178
Chicago ↔ Middletown12 November 202114 November 2021 181 181
Chicago ↔ Mexico City20 October 202122 October 2021 183 183
Chicago ↔ Tallahassee16 October 202118 October 2021 184 184
Chicago ↔ Rochester21 October 202125 October 2021 185 185
Chicago ↔ Fayetteville28 October 20212 November 2021 192 192
Chicago ↔ Omaha1 October 20213 October 2021 192 192
Chicago ↔ Oklahoma City15 October 202117 October 2021 198 198
Chicago ↔ Panama City2 October 20213 October 2021 198 198
Chicago ↔ Green Bay23 September 202126 September 2021 202 202
Chicago ↔ Punta Cana26 November 20212 December 2021 205 205
Chicago ↔ Guadalajara4 November 20217 November 2021 205 205
Chicago ↔ Tucson4 November 20218 November 2021 205 205
Chicago ↔ Charlottesville9 October 202111 October 2021 209 209
Chicago ↔ San Salvador17 September 202119 September 2021 217 217
Chicago ↔ San Jose25 September 202128 September 2021 218 218
Chicago ↔ Fresno25 September 202126 September 2021 220 220
Chicago ↔ Augusta15 November 202121 November 2021 222 222
Chicago ↔ Wilmington28 October 202131 October 2021 222 222
Chicago ↔ Flagstaff18 October 202120 October 2021 228 228
Chicago ↔ Paducah4 October 202110 October 2021 230 230
Chicago ↔ Montego Bay12 November 202115 November 2021 231 231
Chicago ↔ Pasco13 October 202117 October 2021 232 232
Chicago ↔ Allentown8 October 202111 October 2021 239 239
Chicago ↔ Santo Domingo3 December 20216 December 2021 241 241
Chicago ↔ Bogota19 October 202121 October 2021 242 242
Chicago ↔ Columbia18 September 202120 September 2021 246 246
Chicago ↔ McAllen7 October 202111 October 2021 249 249
Chicago ↔ Toronto19 November 202122 November 2021 251 251
Chicago ↔ Monterrey16 November 202120 November 2021 253 253
Chicago ↔ South Bend4 October 20217 October 2021 255 255
Chicago ↔ Spokane20 October 202125 October 2021 255 255
Chicago ↔ Madison20 September 202122 September 2021 256 256
Chicago ↔ Evansville15 October 202117 October 2021 257 257
Chicago ↔ San José del Cabo12 November 202117 November 2021 258 258
Chicago ↔ Leon/Guanajuato23 January 202229 January 2022 260 260
Chicago ↔ Springfield15 October 202117 October 2021 264 264
Chicago ↔ Huntsville8 October 202111 October 2021 265 265
Chicago ↔ Belgrade1 October 20215 October 2021 265 265
Chicago ↔ Rhinelander23 September 202126 September 2021 268 268
Chicago ↔ Monroe8 October 202111 October 2021 271 271
Chicago ↔ Billings24 January 202230 January 2022 275 275
Chicago ↔ Lansing1 October 20213 October 2021 276 276
Chicago ↔ Puerto Vallarta3 February 20227 February 2022 276 276
Chicago ↔ Kingston23 September 202127 September 2021 278 278
Chicago ↔ Nassau8 November 20219 November 2021 279 279
Chicago ↔ Honolulu1 October 20214 October 2021 282 282
Chicago ↔ Milan4 November 20218 November 2021 289 289
Chicago ↔ Aguascalientes9 October 202111 October 2021 290 290
Chicago ↔ Melbourne16 January 202220 January 2022 292 292
Chicago ↔ Bristol, VA/Johnson City/Kingsport22 September 202123 September 2021 294 294
Chicago ↔ Manchester2 October 20213 October 2021 297 297
Chicago ↔ Amsterdam28 October 202131 October 2021 298 298
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If you didn’t see any destination you liked, then search all flights here ✈️.

All prices are based on previous searches. If you click through and the cheap price is no longer visible, it means the flight has been booked out. Try searching alternative dates. Have questions? just ask. Cheap flights may not be available on all days or across all airlines. Restrictions may apply including a ticket being non-refundable or with limited baggage. Always read the terms and conditions and keep a copy for reference. You can view our terms here.


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The Flight Sale Team.

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