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 - DestinationDepartureReturn atPriceBook
ChicagoDallas10 January 202416 January 2024 47 47
ChicagoPhiladelphia9 January 202410 January 2024 47 47
ChicagoMiami1 December 20237 December 2023 67 67
ChicagoFort Myers17 December 202319 December 2023 73 73
ChicagoFort Lauderdale20 December 202321 December 2023 74 74
ChicagoPhoenix4 January 20249 January 2024 77 77
ChicagoTampa10 December 202314 December 2023 81 81
ChicagoLas Vegas5 December 20236 December 2023 82 82
ChicagoOrlando4 December 20236 December 2023 84 84
ChicagoNew Orleans9 December 202312 December 2023 87 87
ChicagoRaleigh/Durham2 December 20235 December 2023 87 87
ChicagoAtlanta30 December 20234 January 2024 87 87
ChicagoBoston14 December 202318 December 2023 89 89
ChicagoHouston13 December 202314 December 2023 89 89
ChicagoKirksville30 November 20233 December 2023 98 98
ChicagoDetroit11 December 202312 December 2023 102 102
ChicagoHartford8 January 202411 January 2024 107 107
ChicagoRonkonkoma25 January 202430 January 2024 107 107
ChicagoSan Diego22 January 202426 January 2024 113 113
ChicagoCharlotte8 December 202314 December 2023 116 116
ChicagoMarion1 December 20233 December 2023 118 118
ChicagoCharleston24 January 202427 January 2024 118 118
ChicagoOwensboro30 November 20233 December 2023 118 118
ChicagoCleveland21 February 202424 February 2024 118 118
ChicagoManistee9 December 202315 December 2023 119 119
ChicagoLouisville24 January 202427 January 2024 120 120
ChicagoNashville8 January 202410 January 2024 120 120
ChicagoDenver8 December 202310 December 2023 125 125
ChicagoFayetteville6 December 20239 December 2023 127 127
ChicagoOklahoma City14 February 202416 February 2024 127 127
ChicagoKnoxville7 December 202312 December 2023 127 127
ChicagoBoise27 December 202331 December 2023 127 127
ChicagoNorfolk24 January 202428 January 2024 127 127
ChicagoEl Paso15 January 202418 January 2024 127 127
ChicagoAustin8 December 202311 December 2023 127 127
ChicagoSioux Falls3 December 20236 December 2023 127 127
ChicagoOmaha5 December 20237 December 2023 127 127
ChicagoWest Palm Beach5 December 20236 December 2023 127 127
ChicagoJacksonville14 February 202417 February 2024 127 127
ChicagoBaltimore12 January 202414 January 2024 128 128
ChicagoMadrid19 March 202424 March 2024 130 130
ChicagoMinneapolis21 December 202323 December 2023 133 133
ChicagoColumbus19 January 202421 January 2024 134 134
ChicagoNew York13 December 202316 December 2023 134 134
ChicagoMissoula17 April 202424 April 2024 136 136
ChicagoPalm Springs23 December 202326 December 2023 136 136
ChicagoSeattle10 January 202411 January 2024 140 140
ChicagoAtlantic City19 January 202423 January 2024 142 142
ChicagoPensacola8 January 202411 January 2024 142 142
ChicagoSan Juan4 December 20237 December 2023 143 143
ChicagoMyrtle Beach25 January 202430 January 2024 144 144
ChicagoRichmond9 January 202411 January 2024 146 146
ChicagoBuffalo31 January 20246 February 2024 147 147
ChicagoBurlington27 December 202330 December 2023 148 148
ChicagoGrand Rapids19 January 202421 January 2024 149 149
ChicagoIndianapolis17 January 202420 January 2024 152 152
ChicagoPittsburgh18 January 202423 January 2024 156 156
ChicagoSaint Louis12 January 202415 January 2024 156 156
ChicagoKansas City4 January 20246 January 2024 156 156
ChicagoPortland15 December 202318 December 2023 157 157
ChicagoFargo29 February 20244 March 2024 157 157
ChicagoWashington10 January 202411 January 2024 157 157
ChicagoMuskegon27 December 20233 January 2024 158 158
ChicagoFort Dodge26 December 20231 January 2024 159 159
ChicagoCincinnati6 January 20247 January 2024 160 160
ChicagoMemphis25 January 202428 January 2024 160 160
ChicagoMason City12 January 202416 January 2024 163 163
ChicagoOntario28 November 202329 November 2023 165 165
ChicagoLittle Rock12 December 202315 December 2023 167 167
ChicagoMiddletown17 January 202422 January 2024 167 167
ChicagoPortland4 December 20238 December 2023 167 167
ChicagoQuincy21 December 202323 December 2023 168 168
ChicagoCancun15 December 202318 December 2023 169 169
ChicagoDecatur5 January 20247 January 2024 171 171
ChicagoBirmingham26 January 202429 January 2024 176 176
ChicagoGreen Bay9 January 202410 January 2024 176 176
ChicagoWestchester County4 January 20246 January 2024 176 176
ChicagoCharleston9 December 202313 December 2023 176 176
ChicagoDuluth6 January 202410 January 2024 176 176
ChicagoRochester8 February 202413 February 2024 176 176
ChicagoTulsa18 January 202421 January 2024 176 176
ChicagoIronwood5 January 20248 January 2024 178 178
ChicagoReno18 January 202422 January 2024 182 182
ChicagoAlbuquerque5 January 20249 January 2024 182 182
ChicagoLos Angeles28 November 202329 November 2023 183 183
ChicagoSaginaw18 January 202421 January 2024 186 186
ChicagoRoanoke19 January 202420 January 2024 186 186
ChicagoCedar Rapids27 January 202428 January 2024 186 186
ChicagoSpringfield14 February 202417 February 2024 186 186
ChicagoWichita15 December 202317 December 2023 186 186
ChicagoAllentown11 January 202414 January 2024 186 186
ChicagoDes Moines9 January 202410 January 2024 186 186
ChicagoRapid City30 January 20243 February 2024 186 186
ChicagoTraverse City17 January 202421 January 2024 186 186
ChicagoGreenville15 December 202321 December 2023 186 186
ChicagoChattanooga12 January 202416 January 2024 186 186
ChicagoSyracuse3 January 20246 January 2024 186 186
ChicagoCharlottesville10 January 202414 January 2024 186 186
ChicagoPunta Cana15 January 202419 January 2024 187 187
ChicagoAlbany26 January 202429 January 2024 188 188
ChicagoSavannah18 January 202421 January 2024 188 188
ChicagoGuatemala City21 January 202425 January 2024 189 189
ChicagoBurlington24 January 202427 January 2024 190 190
ChicagoOakland18 December 202324 December 2023 251 251
ChicagoLexington3 April 20246 April 2024 265 265
ChicagoMontego Bay27 January 202431 January 2024 297 297
ChicagoAguadilla4 December 20238 December 2023 311 311
ChicagoSan Antonio12 March 202417 March 2024 366 366
ChicagoFort Walton Beach6 April 20247 April 2024 411 411
ChicagoHonolulu21 January 202427 January 2024 420 420
ChicagoSan Salvador30 November 20231 December 2023 427 427
ChicagoLa Crosse1 March 20247 March 2024 465 465
ChicagoHavana12 December 202316 December 2023 512 512
ChicagoNassau12 April 202418 April 2024 547 547
ChicagoBelgrade24 January 202428 January 2024 643 643
ChicagoIstanbul7 February 202412 February 2024 811 811
ChicagoDubai24 January 202428 January 2024 874 874
ChicagoParis29 November 202330 November 2023 925 925
ChicagoVienna12 December 202316 December 2023 965 965
ChicagoTallinn5 December 20239 December 2023 1 021 1 021
ChicagoDublin25 March 202430 March 2024 1 029 1 029
ChicagoMoscow15 March 202420 March 2024 1 406 1 406
ChicagoColombo24 January 202428 January 2024 1 412 1 412
ChicagoYerevan15 December 202317 December 2023 1 444 1 444
ChicagoSaint Petersburg5 December 20239 December 2023 1 506 1 506
ChicagoSeoul10 January 202411 January 2024 1 965 1 965
ChicagoBangkok30 November 20231 December 2023 8 250 8 250
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Happy Travels

Cheers,

The Flight Sale Team.

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