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 ↔ Fort Myers11 January 202215 January 2022 41 41
Chicago ↔ Miami9 January 202215 January 2022 41 41
Chicago ↔ Las Vegas9 February 202215 February 2022 42 42
Chicago ↔ Fort Lauderdale9 January 202215 January 2022 55 55
Chicago ↔ New Orleans5 January 20228 January 2022 56 56
Chicago ↔ Dallas7 January 20228 January 2022 56 56
Chicago ↔ Houston20 January 202224 January 2022 58 58
Chicago ↔ Atlanta4 February 20227 February 2022 58 58
Chicago ↔ Orlando17 January 202219 January 2022 64 64
Chicago ↔ Phoenix11 January 202214 January 2022 66 66
Chicago ↔ Tampa8 February 202211 February 2022 68 68
Chicago ↔ Ironwood10 January 202212 January 2022 74 74
Chicago ↔ Santa Ana15 January 202218 January 2022 75 75
Chicago ↔ Cincinnati4 March 20229 March 2022 82 82
Chicago ↔ Los Angeles18 January 202220 January 2022 84 84
Chicago ↔ New York11 December 202113 December 2021 89 89
Chicago ↔ Boston9 December 202113 December 2021 90 90
Chicago ↔ Denver13 January 202216 January 2022 93 93
Chicago ↔ Louisville3 February 20226 February 2022 93 93
Chicago ↔ Minneapolis10 December 202112 December 2021 95 95
Chicago ↔ San Diego20 January 202225 January 2022 100 100
Chicago ↔ Knoxville11 March 202214 March 2022 101 101
Chicago ↔ Nashville13 December 202115 December 2021 105 105
Chicago ↔ Oakland24 January 202227 January 2022 115 115
Chicago ↔ Raleigh/Durham25 January 202229 January 2022 117 117
Chicago ↔ Sacramento5 January 202211 January 2022 118 118
Chicago ↔ Burbank6 December 20219 December 2021 120 120
Chicago ↔ Philadelphia10 December 202111 December 2021 122 122
Chicago ↔ Kansas City20 January 202222 January 2022 122 122
Chicago ↔ Austin23 March 202229 March 2022 124 124
Chicago ↔ San Francisco15 January 202217 January 2022 125 125
Chicago ↔ Saint Louis16 December 202120 December 2021 125 125
Chicago ↔ Baltimore9 December 202112 December 2021 125 125
Chicago ↔ Columbus4 February 20226 February 2022 126 126
Chicago ↔ Lexington12 January 202214 January 2022 128 128
Chicago ↔ Syracuse21 January 202224 January 2022 130 130
Chicago ↔ Myrtle Beach6 May 202211 May 2022 133 133
Chicago ↔ Ontario28 March 202230 March 2022 133 133
Chicago ↔ Portland3 February 20225 February 2022 135 135
Chicago ↔ Salt Lake City13 January 202217 January 2022 137 137
Chicago ↔ San Juan22 February 202225 February 2022 137 137
Chicago ↔ Hot Springs13 January 202219 January 2022 138 138
Chicago ↔ Charlotte7 January 202210 January 2022 139 139
Chicago ↔ Washington16 January 202218 January 2022 140 140
Chicago ↔ Detroit10 December 202112 December 2021 141 141
Chicago ↔ Ronkonkoma10 December 202113 December 2021 143 143
Chicago ↔ Saint Croix19 January 202222 January 2022 144 144
Chicago ↔ Seattle12 January 202214 January 2022 144 144
Chicago ↔ Cedar Rapids17 December 202120 December 2021 145 145
Chicago ↔ Sarasota8 January 202213 January 2022 146 146
Chicago ↔ San Antonio9 December 202113 December 2021 147 147
Chicago ↔ Fayetteville13 January 202217 January 2022 150 150
Chicago ↔ Green Bay6 January 202212 January 2022 151 151
Chicago ↔ McAllen3 February 20228 February 2022 154 154
Chicago ↔ Colorado Springs13 January 202217 January 2022 154 154
Chicago ↔ Richmond8 December 202113 December 2021 154 154
Chicago ↔ Charleston11 December 202113 December 2021 156 156
Chicago ↔ Cancun6 January 202212 January 2022 157 157
Chicago ↔ Concord27 January 202230 January 2022 158 158
Chicago ↔ Greensboro/High Point3 February 20226 February 2022 159 159
Chicago ↔ Middletown16 January 202219 January 2022 165 165
Chicago ↔ Little Rock13 January 202219 January 2022 167 167
Chicago ↔ Omaha18 December 202119 December 2021 169 169
Chicago ↔ Hartford4 March 20225 March 2022 170 170
Chicago ↔ Punta Cana10 January 202214 January 2022 174 174
Chicago ↔ Wilmington19 January 202225 January 2022 176 176
Chicago ↔ Guadalajara2 February 20227 February 2022 179 179
Chicago ↔ Daytona Beach11 February 202214 February 2022 181 181
Chicago ↔ Saint Thomas24 January 202229 January 2022 184 184
Chicago ↔ Lebanon12 December 202114 December 2021 184 184
Chicago ↔ Tallahassee21 January 202224 January 2022 186 186
Chicago ↔ Key West27 January 202230 January 2022 188 188
Chicago ↔ Fort Walton Beach6 December 202110 December 2021 188 188
Chicago ↔ Jacksonville17 January 202220 January 2022 191 191
Chicago ↔ Pittsburgh18 December 202119 December 2021 194 194
Chicago ↔ Buffalo17 May 202218 May 2022 195 195
Chicago ↔ Savannah11 December 202113 December 2021 200 200
Chicago ↔ Panama City8 February 202212 February 2022 201 201
Chicago ↔ Memphis10 December 202113 December 2021 204 204
Chicago ↔ West Palm Beach17 December 202120 December 2021 205 205
Chicago ↔ Columbia7 January 20229 January 2022 207 207
Chicago ↔ Punta Gorda24 December 202126 December 2021 209 209
Chicago ↔ Cozumel15 December 202119 December 2021 213 213
Chicago ↔ Cleveland22 December 202128 December 2021 215 215
Chicago ↔ El Paso28 January 202230 January 2022 215 215
Chicago ↔ Medellin14 January 202218 January 2022 216 216
Chicago ↔ San José del Cabo20 February 202225 February 2022 217 217
Chicago ↔ Asheville11 December 202113 December 2021 221 221
Chicago ↔ San Jose11 February 202215 February 2022 221 221
Chicago ↔ Reno10 December 202113 December 2021 222 222
Chicago ↔ Charlottesville10 December 202111 December 2021 222 222
Chicago ↔ Puerto Vallarta10 February 202213 February 2022 225 225
Chicago ↔ Belgrade11 February 202215 February 2022 228 228
Chicago ↔ Tucson13 January 202219 January 2022 228 228
Chicago ↔ Everett12 January 202214 January 2022 232 232
Chicago ↔ Oklahoma City7 December 202110 December 2021 239 239
Chicago ↔ Montego Bay13 December 202114 December 2021 243 243
Chicago ↔ Santo Domingo12 April 202217 April 2022 246 246
Chicago ↔ Durango24 February 202228 February 2022 247 247
Chicago ↔ Indianapolis17 December 202119 December 2021 248 248
Chicago ↔ Palm Springs27 January 202230 January 2022 252 252
Chicago ↔ Milwaukee24 December 202128 December 2021 253 253
Chicago ↔ Newburgh11 December 202113 December 2021 255 255
Chicago ↔ Albany17 December 202119 December 2021 255 255
Chicago ↔ Sioux Falls7 December 20219 December 2021 256 256
Chicago ↔ Toronto24 December 202126 December 2021 257 257
Chicago ↔ Kingston3 February 20228 February 2022 260 260
Chicago ↔ Aspen8 February 202211 February 2022 261 261
Chicago ↔ Birmingham30 March 20224 April 2022 261 261
Chicago ↔ Montgomery14 January 202217 January 2022 261 261
Chicago ↔ Lincoln24 December 202125 December 2021 266 266
Chicago ↔ Montreal31 December 20216 January 2022 271 271
Chicago ↔ Vancouver14 January 202217 January 2022 272 272
Chicago ↔ Vail7 January 202211 January 2022 274 274
Chicago ↔ Santiago14 January 202218 January 2022 274 274
Chicago ↔ Rochester19 December 202120 December 2021 275 275
Chicago ↔ Flint24 December 202127 December 2021 275 275
Chicago ↔ Nassau22 February 202227 February 2022 277 277
Chicago ↔ Springfield11 December 202113 December 2021 277 277
Chicago ↔ Liberia5 February 202210 February 2022 284 284
Chicago ↔ Veracruz22 June 202227 June 2022 289 289
Chicago ↔ Pendleton6 April 20229 April 2022 293 293
Chicago ↔ Yuma13 January 202216 January 2022 298 298
Chicago ↔ Huatulco14 April 202217 April 2022 300 300
Chicago ↔ Albuquerque31 December 20215 January 2022 301 301
Chicago ↔ Worcester7 May 20228 May 2022 308 308
Chicago ↔ Huntsville28 December 202129 December 2021 308 308
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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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